57: Jack Wilson of Cinch IT - Selling More While Working Less and Being Happier
Sales Success StoriesDecember 04, 2018
57
01:35:4088.21 MB

57: Jack Wilson of Cinch IT - Selling More While Working Less and Being Happier

In one line

Jack Wilson, Director of Business Development at Cinch IT, grew his book of business 223% in his first year using a counterculture 2-4-6-8 daily activity plan, after a top 1% run in business banking at Citizens Bank, proving you can sell more while working less and being happier.

Who is Jack Wilson?

Jack Wilson is the Director of Business Development at Cinch IT, a managed IT services company covering New England. A business major who started out running a 3,000-square-foot coffee shop, he moved into selling outsourced payroll to small and medium businesses, then into business banking at Citizens Bank in Worcester, Massachusetts, where he was consistently ranked in the top 1% of performers and finished a year ranked #4 in the bank. He was brought into Cinch IT by owner Rick Porter not just to sell but to build the sales team, process, and tools from scratch. Jack calls himself a rule breaker and a counterculture, old-school seller, and his approach centers on activity that is measurable and repeatable, keeping a hard work-life boundary so that happiness stays a priority.

Key questions answered

What are the three things Jack Wilson credits for his sales success? Per Jack Wilson (Cinch IT), on Sales Success Stories, there are three: everything you do should be measurable and repeatable (measure the revenue-generating activities, then wash, rinse, repeat), put your success on autopilot (pre-schedule every activity in your CRM so the tool tells you what to do and when), and be contagious (spread your passion and knowledge so people want to be around you). 0:05:20

What is Jack Wilson's 2-4-6-8 activity plan? Per Jack Wilson (Cinch IT), it is a low-but-deliberate daily formula: 2 revenue-generating meetings a day (existing clients, tier 1 partners, assessments, or presentations), 4 networking activities a week (one a day across four field days), 6 highly targeted walk-ins a day, and 8 dials a day to prospects you commit to working through the full 6-to-8-touch cadence. He stresses this is not about working less hard, it is about being hyper-efficient and targeted. 0:48:31

How much did Jack Wilson grow the business at Cinch IT? Per Jack Wilson (Cinch IT), the same 2-4-6-8 plan drove 223% growth in the book of business in his first year, starting as salesperson number one, and his team of three is closing the year at over 126% of goal with roughly $1 million in recurring revenue, up from only hundreds of thousands when he arrived. 0:03:33

Can you really be a top salesperson while working fewer hours? Per Jack Wilson (Cinch IT), yes: after pushing his activity up to 45-to-50-hour weeks in year two and hitting a point of diminishing returns, he treated success like a volume dial rather than an on-off switch, and the epiphany came at a Citizens Bank recognition trip when he realized a higher-effort peer ranked below him while he felt ten times happier. 1:29:53

What is Jack Wilson's sales philosophy and style? Per Jack Wilson (Cinch IT), the philosophy is to follow a value-first process (Cinch IT runs a cybersecurity audit as a free deliverable during discovery) and to be genuinely okay walking away when it is not a good fit. His style is relationship-based, a giver's-gain approach he defends even in the era of the challenger sale. 1:07:50

What advice does Jack Wilson give salespeople starting out? Per Jack Wilson (Cinch IT), be vulnerable: lean into the uncomfortable things like role play, ride-alongs, and call recordings, because the resistance is ego and those tools exist to make you better. For cold calls specifically, throw away the script once you have internalized it and lead with genuine intent. His closing challenge is to do the math: reverse-engineer your own ratios so you know cold how many dials it takes to book an appointment. 1:21:21

Frameworks & concepts

  • The 2-4-6-8 activity plan: 2 revenue-generating meetings a day, 4 networking activities a week, 6 targeted walk-ins a day, 8 committed dials a day, deliberately low volume executed with high targeting and full-cadence follow-through.
  • Measurable and repeatable: design your day around a small set of measurable revenue-generating activities, split-test approaches, and review weekly or monthly whether the pattern still works before repeating it.
  • Put your success on autopilot: pre-schedule every activity and follow-up in the CRM so the calendar and its reminders drive your day, "if it's not in my sales tool, I'm not doing it."
  • Be contagious: spread passion and knowledge like a cold so people want to be around you, a character trait Jack ranks alongside the process-based habits.
  • Leading vs. trailing indicators: focus on the leading activity you control rather than the trailing results (sales, revenue), and trust the reverse-engineered math to produce the outcome.
  • Tier 1 partners: prioritize referral partners whose customers are your customers and whose conversations naturally surface your offering (for example CPAs for payroll reps), instead of treating any referral meeting as equal.
  • The twos: two revenue-generating opportunities every single day, one in the morning (Jack favors a 10 a.m. meeting) and one in the afternoon, in any combination.
  • Success as a volume dial: effort is not an on-off switch but a dial you turn up or down to find the point before diminishing returns, so you can be a top producer and still have a life.
  • Work-life barrier: Jack rejects "work-life balance" (which implies equilibrium) in favor of a hard boundary: leave the phone on the table at home and protect personal life.
  • Will over skill: if the will to reach the top 1% is not there, that is fine, redirect that energy into honing your craft and getting better at what you already do.
  • Most salespeople: Jack's team shorthand for the average behaviors to avoid, such as quoting gaudy activity goals (100 dials a day) they rarely actually hit.

Notable claims

  • Per Jack Wilson, the 2-4-6-8 plan drove 223% growth in the book of business in his first year at Cinch IT.
  • Per Jack Wilson, his three-person team is closing the year at over 126% of goal, worth about $1 million in recurring revenue, up from only hundreds of thousands when he started.
  • Per Jack Wilson, managed IT services companies typically stall around $2 million in monthly recurring revenue, and the goal he set with owner Rick Porter was to scale Cinch IT toward $10 million.
  • Per Jack Wilson, at Citizens Bank he targeted businesses with $2 to $5 million in revenue, aimed for 6 to 8 face-to-face meetings a week, and ran a closing ratio of roughly 50 to 70%.
  • Per Jack Wilson, he climbed from ranked in the 40s to the top 15, was ranked #1 in the bank in January of his third year, and finished that year #4, out of a team of a couple hundred, working out of the smaller Worcester, Massachusetts market.
  • Per Jack Wilson, one rep on his team who is strong at walk-ins converts about 2 face-to-face appointments per 61 doors and closes roughly 1 of those 2.
  • Per Jack Wilson, three reps with very different backgrounds (insurance B2C, relationship-driven high-influence, and his own banking B2B) produced at nearly the same clip, which he attributes to consistency rather than raw talent.

Companies, tools & books mentioned

Companies & organizations: Cinch IT, Citizens Bank, IBM, BNI, Chamber of Commerce, Panera Bread, Starbucks.
Tools: Autotask (ticketing system used as a built-in CRM), Salesforce (referenced as the one he does not use), Feedly, Gong.
Podcasts referenced: Make It Happen Mondays with John Barrows.
Books: Jack references an unnamed book on leading versus trailing indicators but does not recall its title.
Connect with Jack Wilson: LinkedIn.

Quotes

"I'm not an advocate for not working hard. That's not what this is about. Instead, I'm an advocate for being hyper-efficient and being very targeted and very deliberate in how you spend your time and talent." Jack Wilson 0:48:31
"If it's not in, in my sales tool, I'm not doing it." Jack Wilson 0:07:29
"I want you to catch me easy like a cold. When I walk into a room with you, I want you to have that rapport where you feel comfortable talking with me." Jack Wilson 0:09:25
"I don't think work-life balance is a real thing because balance indicates to me sort of like a homeostasis or an equilibrium." Jack Wilson 1:16:50
"Throw every script you've ever had in the trash." Jack Wilson 1:23:24
"I said, well, wait a minute, he's, you know, ranked number 8. Here I am at number 4, and I think I'm doing half as much as him, but I feel like I'm, I'm 10 times happier. And that's the way I want to live my life forever." Jack Wilson 1:29:53

Listen & full episode details on top1.fm →

0:01 Scott Ingram: I kind of had an epiphany. I said, well, wait a minute. He's ranked number 8. Here I am at number 4, and I think I'm doing half as much as him, but I feel like I'm 10 times happier. That's the way I want to live my life forever. That's really what spurred this whole model and this whole process to be successful while having that boundary and making sure that you're happy while doing it. You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm. Here's your host, Scott Ingram.

0:48 Scott Ingram: Today on the Sales Success Stories podcast, my guest is Jack Wilson, who is currently the Director of Business Development at Cinch IT. But my conversation with Jack requires a bit more setup because I'm technically breaking my own rules for guests on this show, but only by a little bit. As a general rule, I only interview active quota-carrying individual contributor sales professionals who are either number one or at least in the top 1% of performers in their respective organizations. And that's why you don't ever hear the usual quote-unquote sales experts on this show that you hear everywhere else. The good news is I'm not breaking the rule by much because in Jack's previous role at Citizens Bank, he was consistently ranked in the top 1% and will certainly discuss that in our conversation today. But the reason I'm bending the rules here for Jack is because of some seriously unique things he's doing currently as a sales leader, but based on his own experience and success. I was recently on John Barrows' Make It Happen Mondays podcast, which Jack happened to listen to. And in that conversation, I was talking about hard work and how I hadn't talked to anybody on that show… on this show… who was at the top of their game who wasn't both working hard and smart, and certainly nobody that was number one while working 30 hours a week. Well, that prompted Jack to send me an email with the subject, I am that guy. And after our first conversation, I knew I had to have Jack on the show. So with that crazy long introduction, welcome to the show, Jack.

2:22 Jack Wilson: Thank you for having me. That's a high bar you set there to live up to, but I love that you said you're, you're bending the rules a little bit because I see myself as, as sort of a rule breaker and a counterculture guy when it comes to sales and being successful. So I'm excited to talk about that.

2:36 Scott Ingram: Yeah, I think so. And I think that there's a lot that we're all going to learn from, from this conversation from, from a number of angles, right? So, we'll certainly talk about some of your own experience as, as an individual contributor in the work that you did and how you were successful by working more efficiently, right? Getting, getting the same results that other people were doing, probably working twice as much as, as you were, but also how you're applying that and building a team. And one of the conversations we've had here a lot on the show recently is Just this idea that I don't think that I've talked to anybody that's at the top of their game despite their boss. And given our first conversation, I think a lot of the things that you're doing as a leader are really, really impactful and important. And perhaps we can also sort of tease apart how you kind of qualify around finding a good leader that you want to work with that's going to help you be successful. Because as I recall, 100% of the people on your team are making their number right now.

3:33 Jack Wilson: Absolutely. Yeah. The entire team. And, and since my inception being salesperson number one, uh, you know, I was given a small book to manage and I took that book and grew it by 223%, uh, in the first year. So we're definitely achieving, the entire team is achieving. And I think starting at the leadership point is a good, a good place for me to break the rules right away. So you talked about finding good leaders. I actually really think that one of the reasons that I position myself as what I think is a good leader is because of a point in my career where I didn't have a leader. I actually, while I was at Citizens Bank and, you know, even though it's a banking role, it's really a, a development role. You're going out, you're finding new relationships, you're introducing customers to the brand, uh, to the bank, sorry. And you're asking for their business. So there was a period in that career where I actually was without, uh, a boss, a leader, a coach, and a manager. They had transitioned to another role. And there was a few months where our entire team was sort of collaborating with one another to try to make sure we were maintaining our activity standards and finding success. And it was during that window in my career. Where I really had to look inward and say, how is it that I'm going to find success without that person driving me and leading me in the right directions? And that's really when I was able to boil down what are the basic activities, what's the premise that I need to set up every single day to achieve success, and how do I do that in a measurable and repeatable manner in order to get the outcomes that I want for myself, you know, really without anyone else putting those pressures on me. I knew I had my own goals. It was time to really figure out how to dive deep and achieve those goals for myself.

5:05 Scott Ingram: Well, and let's use that to transition. I mean, speaking of looking inward, and I know that'll transition well into your first point here, we always kind of open off with immediate value and talk about the top 3 things that you believe have contributed the most to your own success. So talk us through those.

5:20 Jack Wilson: Yeah. So the first one is being… everything that you do should be measurable and repeatable. You know, we have a limited number of time. In our day, and to be efficient with that time, you've got to measure what are the activities that are going to lead you to success. So measurability is so important, and, you know, using your tools to measure the outcomes of that, you got to determine what it means for that activity to be successful. In my life, I look at those activities as being potentially revenue generating. So obviously, you know, your cold calls, your walk-ins, your dials, your social media outreach… what are you know, the small measurable number of activities that you could design a plan around that's gonna help you get to those outcomes. And then, you know, we, you talk a little bit on the podcast about split testing and making sure you're, you know, if you're gonna try one approach or one dialogue, make sure you measure that against another approach and dialogue and really measure how many appointments did I book based on that? How many of those appointments led to closed deals? You know, even get as granular as what was the revenue generated from that specific, very specific activity. And to really reverse engineering those numbers to saying, okay, every day, I've got 8 hours in a day. I don't want to be working 9, 10, 12 hours if I don't have to. What mix of activities do I lay out for myself? You know, in what amount of time in order to achieve those results? And then the last part of that is making sure it's repeatable. So when you measure it, if it's coming up with the outcomes that you want, they're going to lead to success. Wash, rinse, repeat. Keep doing those activities. But repeatable doesn't just mean doing them and doing them and doing them. The definition of insanity, you know, doing the same thing, expecting different results. You've got to measure the success of that same pattern as well. So having a period of time, you know, whether it's weekly, monthly, to sit down and really review if that pattern of activity is working for you and if it's not, trying something new and then adding that to your mix, measuring it, and then really, you know, defining what that cycle looks like for you so that you can constantly keep up on your game and make sure you're doing the right activities to lead to success.

7:16 Scott Ingram: Awesome. And we'll definitely dig into that a little bit more in terms of what the specifics were around those actual activities, both for you and also kind of what you've set up for your team. So the first piece was being measurable and repeatable. What's number 2?

7:29 Jack Wilson: So number 2, I would have to say, is a little kind of slogan I put together that says, put your success on autopilot. I actually don't think that the human brain is all that great. I think there's major limitations in what we can think about and how many thoughts we have in our head, staying focused, keeping on tasks. But when I say put your success on autopilot, it really revolves around using the tools at your disposal to make sure that those patterns that you've defined work for you are set up in a manner that you could just execute on them. So, you know, in my daily life, it's, it's using a CRM tool to make sure that I've pre-scheduled all of those activities. You know, kind of go back to time. Time is that one resource that's so limited. And my whole goal is around being as efficient as possible. So instead of just saying, I know I'm going to do these activities, I know I'm going to do X amount of those activities, well, let's be specific and say when and pre-schedule them. And then even go a step further where all the tools that you use should be reminding you when and how to do them as well. So when I wake up in the morning, you know, I've already done my preparation the night before to look at my calendar and know what's going on. But the amount of alerts and tasks and reminders that are going to pop up when I start my day tells me exactly where to be and when to be there. I'm sure you've heard the expression from salespeople that says, if it's not in Salesforce, it doesn't exist. You know, I don't necessarily use Salesforce, but I use a similar CRM tool and I live by that same moniker. If it's not in, in my sales tool, I'm not doing it. So when I wake up that morning, I've got all my prescheduled activity that tells me exactly what to do, how much to do it, and when to do it. Yeah.

9:04 Scott Ingram: So Jack, what, what is that CRM tool?

9:06 Jack Wilson: So we actually use a ticketing system. So I'm in the IT industry and we do managed IT services. So our ticketing system is called Autotask and Autotask actually has a built-in CRM tool that we've been able to customize and work to fit our needs without having to go out and get some of the larger tools like Salesforce Awesome.

9:24 Scott Ingram: All right. So number 3.

9:25 Jack Wilson: So number 3 is be contagious. And it actually took me a little, a little while to think of these 3 because there's so many things that you do to, to try to be successful. And I, and I think they evolve with your career, with your life, and, and when you find different success. So this one really took me some, some deep thought to figure out, you know, I don't want necessarily all process-based kind of things in my life that lead to success. It's, it's gotta be a lot about your character too, and, and who you are as a person. And as I thought back to my different careers and, and maybe even thought about What would people say about me if you asked them what you thought those top 3 things that led to success were? I think people would say that I'm contagious. What does that mean? I want you to catch me easy like a cold. When I walk into a room with you, I want you to have that rapport where you feel comfortable talking with me, but it extends into my behavior and my activities and the passion that I think that I have for whatever it is that I do. Being contagious, it's not just about the people around you. The more contagious you are, the more passionate you are about your career and your life, the more it's actually going to build within yourself. You know, you've always heard the old moniker of if you just try to have a positive attitude, you will. If you walk around with a smile on your face, you have no choice but to be happy. Well, if you walk around in your life being contagious, trying to spread your success to everyone, you're just going to promote yourself to be even more successful in your own life. And I think from a leadership perspective too, It being contagious with your knowledge, with your skillset, just like you do on the podcast, make sure you share that wealth of information with everybody around you. It's going to want to make people be around you more and share their insights and their knowledge. At the end of the day, you know, I had a great mentor when I first was in college and I'd switched to a business major. He was a gentleman that was a senior vice president of IBM at one point in his career. And it's really hard on the class. He actually, he taught us as though we were in the corporate environment and really held us to high standards. And he used to say, you know, sit down and eat or we'll both starve. And to me, that really meant you've got to take what you have, spread it to those around you like a wildfire, and really be contagious in everything that you do.

11:25 Scott Ingram: That's awesome. And that's, that's a really good contagious. And I hope, you know, if you're listening to this, that you'll help us make this contagious. I have a feeling this is going to be a really, really impactful conversation. I'm already feeling it with, with Jack here already. And it's a better contagious than I perhaps am right now. I'm Getting over the tail end of a cold. Turns out traveling halfway around the world and recovering from a 10-hour time lag in Dubai is not so good for your body. So, if my voice is a little off, that's, that's it. I'm drinking extra lots of water during this conversation. So, Jack, let's, let's contextualize this a little bit, starting with your current role and its evolution at Cinch IT. Talk, talk about kind of how that all came about and what you've been working through there.

12:08 Jack Wilson: Sure. Well, I, you know, I tell you, it kind of harkens back to being contagious. I started my career not really in sales. I actually came out of college and, you know, I was a business major and I said, you know, I could do this. I could do this. I'm gonna start a business and I'll make enough money to pay myself and be happy. And there you go. That's the rest of my life. And I actually grabbed a friend of mine that was in college with me at the time and I said, let's open a little coffee shop. You know, we'll just sell coffee, have a good time, and we'll pay ourselves a livable wage. So we actually went about doing that, you know, and we actually ran across a couple of gentlemen that were starting a franchise in the area. We just wanted to have an interview with them to talk to them about, you know, where it is that you get your stuff, how do you operate the business, and that conversation slowly turned into getting us involved in what they had going on. So the close friend of mine and I, we actually went off and jumped in as part of that endeavor, and we helped them open up a coffee shop, and we ran that for a couple of years. So we dove right into small business, running a business, being an entrepreneur. It was actually while I was running that coffee shop that I met the folks that had started Cinch IT. Now, it wouldn't be until 10 to 15 years later that I ended up getting involved with them on the business front. But being contagious, if I didn't have the approach to life and that outlook of making sure everyone knew who I was and appreciated who I was and I was doing anything I could do to be helpful, that relationship wouldn't have fostered, which later led to that career. So let's fast forward through all the boring stuff and skip to when I was actually at Citizens Bank. I was a business banker managing the relationship with Cinch IT. And when they approached me to say, hey, you know what, we really love what it is that you do for us. We love the relationship, your responsiveness, how it is you treat us as a We want to take that and we want to now go give that to our customers and we want you to do it. Come be a salesperson for Cinch IT. And I said, no. I said, absolutely not. I'm already a salesperson. Why do I want to go be a salesperson in a different industry that I've never known before and have no experience in? Sounds crazy, especially when I'm at the top of my game in the banking industry with a bank that does a great job and had a fantastic culture. So I kept in touch with, you know, the owner at Cinch IT and he kept hammering on me and said, you know what, come over, come join us, come to the dark side. And eventually the conversation transitioned to, you know, we realized that it's not a salesperson that we need or an account manager that we need. We really want someone to come in and fundamentally transform the business, you know, come in, build a team, find some success themselves, do the development and actually produce, but also develop the processes and the tools, the team and the individuals it'll take for us to go to the next level. You know, in IT, there's a million managed service companies in IT, and they usually all get to a point where their MRR is around that $2 million mark, and they, they fizzle out. You know, it's… that's the point where scalability really becomes important. It's how do we go from $2 million to $10 million, or do we just stay here and be kind of happy with what we have going on? And, you know, I basically spoke with Rick Porter, who is the owner of Cinch IT, and said, hey, if I come on board, we're gonna break the company. That's our goal. And he said, let's do it. Let's break the company. So I took the risk. I took a chance. I left a career that I was fantastic at, that I loved, that I had spent a lot of time developing that system for success, and I jumped into something brand new where I had to start sort of all those processes and tools and create them for myself from scratch.

15:29 Scott Ingram: Awesome. And as I understand it, I mean, you basically came in and did the role yourself and then have since then been scaling and building a team.

15:38 Jack Wilson: Absolutely. So you're not breaking the rules that, you know, that much. I am the number one producer, and it was on a team of one at the time, but that's still the top 1%. So you're right in line with that. But yeah, when I, when I first came on board, I was, you know, salesperson number one and, you know, the director of business development. So it was go out, find some success for yourself, still find the time to do the activities that are gonna lead to new relationships and grow the business. While on the other hand, developing the sales process, you know, creating some tools, helping realign some of the marketing and things along those lines to really position us to a place where we could grow rapidly. You know, rather than doing what all those other managed service companies do that fizzle out at the $2 million mark, how do we get some tools around us so that we can add individuals, plug them into the system, train them up, and then coach them to where they can get to the wildly successful point that I was at as well.

16:29 Scott Ingram: And how big is the team now?

16:30 Jack Wilson: The team now is about 3 individuals total, not including myself. We cover all of New England. So it's funny, when I listened to the podcast, I heard someone mention, you know, oh, you know, most of the people you interview, they must be single, they don't have a family. Well, my misconception was most of the people you interview work for these giant Fortune 500 companies or sell into large enterprise. And I thought a lot of those lessons and a lot of the skills can be applied at a small company. So even though it's a team of 3 and we sell regionally, really in New England right now, a lot of those practices that we employ can be used on the enterprise level. And I think sometimes when you get into that enterprise level and you have all the tools like the lead generation tools, an inbound team of SDRs, sometimes those reps in those field positions actually forget the basic tenets of what it means to be, you know, a good outside sales rep. So a team of 3 right now. That team, we're at… actually, we're about to close the year over 126% of the goals that I've changed after coming in, which is a big deal. You know, the team's worth about $1 million itself just in recurring revenue, and that's coming from a company that was in only the hundreds of thousands when I first showed up.

17:37 Scott Ingram: That's awesome. So now let's fill in the details in the middle just a little bit. And where did sales come from, right? So you were running this coffee shop. At what point did you make the transition into a a true sales career.

17:49 Jack Wilson: So, you know, the coffee shop that I had was a different model. We were kind of just a big, huge 3,000-square-foot space with free Wi-Fi inviting everybody in to do work. And really, it was at the beginning of, you know, when Starbucks was really taking off and the Panera Bread was where everyone goes after their networking meetings to do their work. And we wanted to be that place. So naturally, most of the professionals that used our space were folks in the sales industry. So one of the individuals that I got a chance to really befriend is a customer of mine. Was someone who worked in a payroll industry. So I think they call it human capital management now, but back then they actually were our rep to sell us a payroll service. And I really got interested in that because it was something I knew nothing about, but I saw that person's lifestyle. I said, wow, they're, they're at my coffee shop 3, 4 days a week, couple of hours at a time. You know, they, they clearly have some freedom and flexibility in their life. What does that type of career look like? And it actually turned into a conversation where they were looking to hire someone to be a sales representative. And I had the opportunity to interview and it was at about the same time that, you know, I'd been in, in the small business world, entrepreneur role for, you know, 3 to 5 years, and there's definitely burnout. It was the food industry, which is really tough. My heart goes out to anybody in the food industry, especially who owns their own business, because at the end of the day, you know, the buck stops with you. And I had kind of got to the point where I was ready for a new challenge. I was ready to enter the business world and really see if everything I learned, you know, back in my college days I could put to use, and if I could find some success for myself and challenge myself in a new path. So I did it. I took the interview, I landed the job, and I went to work for selling payroll, outsourced payroll services to small and medium-sized businesses.

19:25 Scott Ingram: Awesome. So what about the interim? So how did you go from payroll into banking? Although that's not a huge, huge leap.

19:32 Jack Wilson: Yeah, no, I actually went right from payroll to banking. So again, it's kind of crazy. It's 2 different industries, very different backgrounds. But when I was working at the payroll company, they had a partnership with banks. You know, part of the activities that I would do on a regular basis was to meet with bankers to say, hey, you know, your customers want to be successful and you as a bank are trying to co- them and give them advice and act as a consultant to help them be successful. Well, one of the things I could do from a payroll aspect is, you know, help improve their efficiency and lower their costs and all that. So that conversation every day with different banks was happening, and they had a particular relationship with Citizens Bank where they were their preferred bank partner. So I actually transitioned from a territory rep at the time with the payroll company into being a liaison with the bank. It was a role where my job was really just to work with their local branches to help coach up their staff on, you know, how to make a qualified referral to us, how we can help their customers, and to foster that relationship. So managing the relationship with 21 different local bank branches and working with a couple different business bankers on their team. So it was that relationship that fostered the conversation. Again, I think from being contagious, I think from having the right attitude and working well with them, that they said, hey, we've got a guy transitioning out into a different territory. We really want to plug you in and invite you to come into the bank and do what you're doing from the payroll world Take that same attitude, that same process, and plug it into the bank and see if you could be successful there. So I did. Again, another opportunity that kind of presented itself that was new and different. But I realized that at that point, I started having the click, that aha moment that said, you know, are these opportunities really all that different? You know, am I managing my life any different, you know, despite the role? And it's not. It goes back to that measurable and repeatable. You know, what are the basic tenets and activities that I'm gonna have to do to find success in that role? Let's make sure I obviously do the training and hone my skills and my craft to bring up the skill level. But as long as I'm doing the right activities and putting myself in the right places, I'll find success. So let's do it. Let's take the risk. And I did. And I jumped into the banking industry and was there for a very long, successful time.

21:38 Scott Ingram: Awesome. So, I mean, that's a pretty good variety of experience, right? You had payroll, you were in banking, now you're in IT. If you were starting all over again today, knowing what you know now, is there anything that you would do differently? Or where would you go? Where would you get a start in today's environment?

21:53 Jack Wilson: You know, honestly, I hear that question a lot, and it's gonna sound a little tacky, but not only would I not change anything, I would hope that if I started all over again, I didn't have the experience and the knowledge that I have now. Because, you know, a lot of times you say to yourself, oh man, if only I could go back and I knew this, I would have done this. And but that ultimately wouldn't have led to the same outcome. You know, it's gonna create a bias for decision-making where your path could have taken you down a totally different way. And my background is definitely eclectic, and I don't want that to change. And if I… if presented with that opportunity again, I want the opportunity to, to be presented with challenges that seem like they don't fit, and finding a way to find the transferable skills and take those behaviors and patterns and learn from them and constantly hone myself as a professional and an individual. So I wouldn't change it at all, and I would hope not to taint my decision-making ability with the bias of what I know Yeah, fair enough.

22:52 Scott Ingram: So let's get into really the reason that you and I initially connected. And I'm curious to know kind of where, where did it come about? Where did you find this ability to achieve at a high level while doing it with a reasonable amount of effort? Where did that all start?

23:09 Jack Wilson: So I was at Citizens Bank for a total of a little more than 3 years. And you know, that what that path looked like was, you know, the first year you get into a new role, and I'm sure everyone's experienced it. You've got to get your feet wet. You've got to learn, you know, what it is the product is that you sell. You've got to learn how your customer buys that, you know, why it's important to them, what impact you have on them. You have to learn the culture of a new company and really the politics of the company. Who are the partners that you need to work with internally to position yourself to get things done? And so the first year, you know, in my role at Citizens Bank was really doing a lot of those things. So I didn't find wild success yet, although I was still ranked in the, you know, above the top half I was kind of in, you know, sort of a middling position where it was… I was doing enough to satisfy my leaders. I was doing enough to satisfy myself, but it was really still honing my craft. At the end of that first year, when I really started to get it, you know, what it is that I do, what it is, the value that I bring, what differentiates me from my competition. As I mentioned before, I had a leader transition out of the role, and the manager I had been working with was one of the best coaches that I had ever worked for. His approach to leadership wasn't wasn't by the numbers, wasn't trying to hold you over accountable for goals and production. His was about the process and the style and the method of what you do. So, you know, if you make a cold call to, you know, a potential client, it's really diving deep to, well, what is it that you said? Why did you say that? How could you say it differently? And then understanding the why behind that behavior and then having you go back and do it again. A lot of role-playing, which at the time I hated. I, I don't think anybody that, that says they love role plays being honest with you, because it, it's like a love-hate relationship until you really understand the value of it. So, but he was a great coach, and I went from having a great coach and thought leader as a manager to he transitioned to a different market, and I went through a period of several months without a leader at all. So we had, uh, the director of our region at the time overseeing several teams of individuals, and the teams were, you know, 10 to 12 business bankers per team. So you're talking 30, 40, 50 individuals spread across pretty large geographies that this person had to now manage. So, as you can imagine, we didn't get a lot of face time. There wasn't the ability to just pick up the phone and troubleshoot an issue or run over your approach to a client. So, it was in that 3 months that I realized I've really got 2 paths here. I can keep muddling along doing what it is that I'm doing and being a middling producer, or I could try to step up in a void and find a way to lead myself And by default help lead those around me. So I did that. I really took the time to say, you know, what are the things that are leading to success? What kind of activities? How many of those activities do I have to do every day? How do I organize myself without somebody coming in and helping giving me that pattern and that path? And that's really started what started me down this routine of learning and self-checking and creating a process for finding success.

26:10 Scott Ingram: And so let's get into the specifics here at this point, right? So what did that boil down to? I mean, on, on either a daily basis or weekly basis, what were you measuring and what were you holding yourself accountable to that was producing the results?

26:24 Jack Wilson: So at the end of the day, it's, it's getting face time in front of potential clients. And before even getting face time in front of those clients, it's understanding who those clients are because you've got to call a number of them. So at the time I was looking for businesses that, you know, the revenues were between $2 and $5 million. So it was finding out, okay, how many of these folks do I have to reach out to to secure that face-to-face meeting? How do I reach out to them? How do they like to be reached out to? So I started testing. Is it the good old-fashioned cold call? Is it picking up the phone and making dials? Is it even the walk-in? I actually still do a lot of walk-ins in my career. I call myself an old-school seller. Is it the walk-in that's going to do it? Is it partner meetings? So the 3 main activities that led to the meeting were were dials, cold dials, walk-ins, meeting with what we called centers of influences, and then also networking. So it was taking those basic activities and figuring out how much of those do I have to do to get the right amount of meetings per week. And the right amount of meetings per week then was about 6 to 8 face-to-face meetings. So, you know, I knew if, you know, 5-day work week, if I was meeting with 2 qualified businesses a day, I'm going to over-index on that number of meetings. And really that's going to result in a final closing ratio of at least you know, 50 to 70%. I know that's a wide window, but banking is a little bit different from, you know, most sales where you're not just getting an agreement, signing a deal, and moving forward. There's a lot of moving parts to transition someone over. But yeah, if I had 6, you know, 6 to 8 meetings was the target, but if I overexceeded that and got to 10, then I was really finding a level of success.

28:01 Scott Ingram: And what was… what did that mix end up being? I mean, what, what really produced in terms of the calls and the walk-ins and the networking and the other things that you were doing?

28:11 Jack Wilson: I love to say it because it was the, the good old-fashioned cold dial. It was dialing into decision-makers at the right-sized company. So being laser-focused on making sure I was calling only those clients that would fit, you know, folks that were going to be really good relationships, folks that I could provide with the services that was going to make a difference. But if I made… at that time it was about 20 dials a day… if I made 20 dials a day, I was going and book at least 2 appointments in that session of 20 dials. So I try not to do that 20 dials all at once. You know, I try to do it, you know, 10, you know, a block of 10 here, a block of 10 there, try to mix it up. Another thing I really started to learn is the diversity of your activity too, you know. So, you know, if I'm calling the same type of businesses on a Monday morning at 10 o'clock and no one's answering, well, maybe this type of business is doing something Monday at 10 o'clock. So diversifying that activity, making sure the follow-up comes on a different day, a different time of day, and then even again that 3rd and 4th and 5th follow-up, making sure that every approach is a different method to reach contact.

29:17 Scott Ingram: And what about… so the cold dials seem to produce the most consistently. What about the other channels and the other things that you were doing? How did that fit in and how did they work into the equation?

29:26 Jack Wilson: Was that just kind of gravy that helped you get to the 10, or what did that look So I actually, I don't think anything that you do is gravy because, you know, when I, when I look at it like that, it's saying, well, I don't actually have to do that activity. It's just kind of a nice add-on, right? So I try to avoid the mentality of thinking any one particular part of my toolset is gravy. Instead, I, I take a holistic approach. So, you know, for example, today, you know, in, in my role at Cinch IT, I actually have a pie chart of sources of business that I share with the team and I say, okay, here's your book of customers. Where did they come from? And we track all that. You've got to have that data. Everyone does. That's what CRM tools are so powerful for. And we, we break down their book of business and find out where they actually came from. What was the lead activity that ended up in a result of them being a client? So we take that pie chart and break it down from your dials, your walk-ins, your networking meetings, your partner meetings. And partner meetings, when I refer to that, it's not having a formal relationship with a partner. But we actually have what we call a tier 1 partner. So if we look at someone in another industry that their customer is our customer, that's the ideal type of business we want to be in front of. That's the first qualifier for a tier 1 partner. The second part is, is whatever we do, does it come up naturally in conversation or can we coach them to where it will naturally come up in conversation? So, you know, back to the payroll days, a lot of payroll reps are meeting with more CPAs than you can imagine. You know, they're meeting with every CPA. In their territory, because obviously an accountant and payroll and taxes… that all makes perfect sense. So their customers are their customers, and it's natural to come up in conversation. So in the banking world, you're working with real estate professionals who are trying to sell you know commercial properties. You're working with attorneys who are closing deals for you. A lot of those other professionals that again are tier one partners. So when I look at partnering, I think a lot of sales professionals will take meetings with folks that they think. That, hey, I can foster a referral relationship here, but you've got to be specific about it. Because if you're meeting with somebody, and it's just like with clients, if it's not an ideal fit, that time that you're spending, you know, it's got its own ratio. And as much as it's also measuring the effectiveness. So that's why I've come up with sort of like a tier 1 versus everything else, because I want to spend the bulk of my time on those individuals that I know there's a very high likelihood that I'm able to get a referral out of them that's going to qualify for my business. So instead of being Gravy, those side activities, every bucket from that pie chart of sources of activity has a delegated activity level. The way you look at it, I was just coaching one of the guys on my team today. He's amazing at the walk-in, the good old-fashioned knock on the door, introduce yourself, walking in and getting business. He's amazing at it. His background is not from sales. He was actually involved with the coffee shop with me way back in the day and I think I loop him into everything that I do and make him suffer through every new project that I start, but I've coached him into becoming a great sales professional. And the walk-ins, his ratio, if he walks into 61 doors, it's going to result in 2 appointments face-to-face. And of those 2, he typically closes about 1. So that's just one piece of that pie chart. But as I coach him, I say, you know, look, that one source of business out of, you know, 5 to 7 sources of business, if you just do those activities You divide that activity out over your available time, you can count on one sale coming from that source. You do that same activity or that same exercise with every other area of expertise that you have or every other tool in your kit, and you get those numbers and you just execute on those numbers. Next thing you know, if your goal is 7 businesses and you got 7 tools and you're doing enough activity to get that one closed deal, you've got 7 new relationships in a month. And you're just taking a very deliberate, focused approach on hitting those very minimum basic activity levels to get there.

33:27 Scott Ingram: Awesome. Well, and we will dig some more into kind of what that model looks like with, with your team. But I want to talk about your results specifically at Citizens and talk about kind of years 2 and 3 and what that looked like. But before we do that, let me say that this episode is brought to you by the 2019 Sales Success Summit. And in an effort to keep this episode a little bit more evergreen, I'm not going to talk about the current offer at all. I'll just ask you to go check out all the details at top1summit.com. That's top1summit.com for all the details. And I promise you, the sooner you do it, the better. top1summit.com. And I hope to see you here in Austin next October. So Jack, let's talk about what the… what did your results look like once you kind of settled in and you figured out this model and you got into this routine and you got the measurable activities and you executing against that. How did that translate into what you were able to achieve initially starting at Citizens?

34:24 Jack Wilson: Yeah, so I think the best part about that starting to translate was they had some goals that were set that, in my opinion, were actually maybe a little unrealistic. You know, when we first started in the field, it was… they were looking for 12 face-to-face meetings a week, you know, with qualified business owners. And at the end of the day, to get that type of activity It was difficult. It was challenging, and everyone who's been in sales knows you know if you have a goal that you don't think is attainable or reasonable, it could set you back because sales is a mental game. So you've got to make sure that your goals that you set for yourself are what you think are reasonable. They should be challenging. They should never be easy, but you've got to think that they're at least achievable. So what I started doing was focusing on just the activity and and really putting the goal aside for a moment. You know, trusting the process, trusting that because I've reverse engineered the math and understood that if I put in this amount of activity, I get this amount of output. And I just trusted that and I started to just plug away and really change my mind. I had read a book and, you know, I feel bad because I don't actually remember the title of the book I read, but it was… it really talked about leading indicators versus trailing indicators. So your trailing indicators being the results, the sales, the revenue, and the leading indicators being the activity. And I took it to heart and I started really focusing my life on those leading indicators. In those leading activities. And lo and behold, I started realizing, well, wait a minute, I don't have the 12 meetings, but I've got between 8 and 10 every week, and I'm doing it in a manner that's reasonable, and I've got plenty of time to do it. And then I started to hone my skills and get the closing ratios better. And that success didn't translate slowly. It actually happened pretty meteorically. I went from kind of being ranked in the 40s out of a team of a couple hundred to shooting right up into the top 50. And it was when I was in the top 15 in the beginning part of that second year that I really realized, well, wait a minute, I can make this happen. I'm just going to keep using my process. I'm not going to worry about those weekly goals that I think are a little high because I was actually consistently missing those. And I'll admit that. I was consistently missing the 12 meetings, but I was consistently meeting my activity standards, which was actually producing better results. Results. So, when I saw that 15, I said, I'm close to the top and it feels like it's a wasted opportunity if I really don't start to over-index those activities to really find a way to achieve. So, I started dialing up the activity levels a little bit more. And, that's the point where I actually worked the hardest. That was the moment in my career where I started working the 40-, 45-hour, 50-hour weeks. You're taking calls at night, you're taking calls on the weekends, making sure to answer clients, And a couple of quarters after doing that, I realized, well, wait a minute, I'm still successful, but it hasn't actually had an exponential increase with the additional activity that I'm putting in. So I realized that there's really a point of diminishing return. So I said, how do I, how do I make sure that I have that work-life balance moving forward where I could be a top achiever, but I'm also not breaking my back? And I started, you know, sort of messing around with what that ratio looked like. And, you know, it's… success isn't an on switch. You don't click it on or off. It's really a volume dial. So it's how do you crank that volume dial up and how do you increase that success, or how do you crank it down? Maybe not just the success, but the input that you put into it. So by the end of that second year, I felt like I understood what that pattern looked like, how much activity I need to put in to be successful. And I know that saying I understood what it felt like isn't a metric, and that totally goes against everything I believe in. And that's why January of that following year. The first rankings came out in the first month of that year, and lo and behold, I was number one, and I was blown away. I didn't expect it. As much as I measure myself, I thought that, and it's a peer ranking type of environment. I thought that it'd be close to the top, but all of a sudden I saw that number one next to my name, and I said, "Son of a gun, it works." I'm now going to wash, rinse, repeat, and just keep doing the same things that I'm doing at the level that I'm doing, and trust the process, and trust that I'm going to succeed. And I end up finishing that year number. 4 in the bank. And I work out of a territory that if anyone's familiar with it, I live and worked in Worcester, Massachusetts, which not a lot of people know where Worcester is. And that market compared to Boston, compared to New York City, Chicago, Philly, Pittsburgh, a lot of major cities. And I was able to, to, you know, come out on top from reps in those markets that folks would perceive to be easier to be successful in.

38:57 Scott Ingram: So what's the recipe for kind of finding that sweet spot like you did? Right. So how do you get that dial right in the right spot where you're getting some great results and you're ending up at the top, but you also still get to have a life and you're not killing yourself?

39:12 Jack Wilson: Well, I think it's, it's understanding when you feel that, that, that stress and that pressure. You know, everybody has that moment where they're saying, you know, I, I think I'm putting in a little bit more than I'm getting out. And it's, it's having this self-awareness and doing a lot of self-reflection to understand when that point happens. But, you know, a lot of You talked about finding good leaders. It was at this same point where I got a new leader and a new manager on our team, and that leader, his mentality and his approach just so happened to fit with mine very well. He was the type of leader that if you're succeeding, if you're doing well, if I know you're doing the right things, I'm not going to bother you at all. There's no micromanagement. There's still a system in place. There's checks and balances. We need to make sure that the work is happening. It's happening in the right ratios. You're tracking. It, all that good stuff. But it was really, hey, you're on an island. If you're doing it and if it's working for you, go do it. And that leader said to me one day, you know, we were working on a really challenging deal and I think I called him at 8 o'clock at night. And he actually said to me, he said, you know, listen, is this going to get approved tonight? I said, well, no, of course not. But he says, well, if it's not going to get approved tonight and if it's not saving anyone's life, it can wait till tomorrow, right? And, you know, although it was a simple conversation, I realized, you know, how many times do sales professionals take that workload and carry it over the threshold of bringing it into your family life where if it's not going to get done today, is it going to get done tomorrow even? Probably not. And if it's not going to get done tomorrow and there's no deadline behind it, don't just push it off because that's kicking the can down the road. But let's take a look at our time, which we can measure, and let's plan the time to do that activity in relation to the actual due date when you need to get it done. So I started taking activities at the end of my day that I had hadn't got achieved yet and saying, that's not a failure. It's just not done right now, and prescheduling the completion of that task for the next day, maybe the day after, but for an open space in my calendar. And then, I really started getting serious about having my calendar drive my life. So, you could start to put things in their own buckets, blocking off time. I think time blocks is a big part of that because you don't actually know how much time you're spending a lot of times when you're just out out in the field flipping over every stone trying to get a deal done until you start proactively scheduling it on your calendar. And I think a lot of sales professionals will be surprised if you block off time and you treat that time just like you treat a face-to-face appointment with a potential prospect and you sit in that, let's say it's an hour and you sit in that hour of time, you dedicate yourself in a focused manner to that task. And when that hour is over, you stop that task, I think you'll be blown away by how much time you actually have left over. Because I think a lot of times we plan, you know, a block of hours to, you know, one block of time to, I don't know, prepare a presentation, to put together a pitch deck. And then that hour bleeds into an hour and a half or bleeds to an hour 45 because you get distracted, you're checking social media. But if you stick to the hour, you stop yourself, you pre-schedule the next session to finish that activity. You're gonna find there's a lot more time left over in that calendar for you to do things. And if you just take that deliberate approach to planning everything that you do and then working that plan, I think a lot of people will find there's a lot more extra time left over in their day that they didn't think they actually had. Nice.

42:36 Scott Ingram: So let's dig into that in a little bit more detail. And one of the questions I typically ask is just give us the… walk us through a full typical day, right? The alarm goes off, what time does that happen? What happens from there?

42:48 Jack Wilson: Sure. You know, it's funny, I was listening to one of the previous episodes and I heard someone say they, you know, they get get up at like 4 in the morning. It might even have been you. And I wish I could get up at 4 in the morning, but I am the worst early riser ever. I wake up usually around 6 o'clock. I hit the snooze button like everybody else. 6, 6:15, I roll out of bed. Part of my routine in the morning that I, I think is really cool is I get up and I make breakfast every day for, for my wife and I. You know, I always have a running joke that I think my wife does more of the hard work in the family, so the least I could do is cook breakfast. So I wake up 6:15, start to make breakfast. Usually by the time I sit down, I like to have at least 10 to 15 minutes to take in some news, figure out what's going on, check out my Feedly to see what's going on in the environment. And that 10 to 15 minutes is also scheduled. I say, hey, at 7:30, I'm going to jump in the shower, get ready, and get out the door. So that's usually the morning. I'm very quick getting up and getting ready. I don't waste a lot of time there. I don't work out in the morning, unfortunately. That's another thing I hear a lot of sales professionals getting up really early to work out. Please tell me how you do that because I'd love to add that to the routine. But then it's, it's hit the road. And when I hit the road, I actually have a pretty decent commute to my office. It's about 45 to 50 minutes, which I actually think is invaluable because that's when I take in a lot of my content. You know, it's listening to your podcast, it's listening to John Barrows, a couple other different podcasts. And I try to split it up. I try not to have it, you know, be all business all the time. I try to listen to a little radio, a little sports radio. You know, I love fantasy football, so I gotta, you know, make sure know my waiver picks for the week. But I listen to a little sports radio. It's… my pattern's kind of funny. I listen to it before I get to the coffee shop. When I get to the coffee shop and get my coffee, it's game on. It's time to listen to the professional development type stuff. And then when I get to the office in the morning, it's really cranking out the must-dos first. So cleaning up the email inbox, and usually it's doing the responses first, you know. So the people that reached out to me maybe late in the day prior that, you know, wasn't something that I could get to right away, make sure to respond to them right away. You know, sending out any proposals or quotes right away, following up with all my prospects. And then it's really diving into what those time blocks are. There's no pattern behind those time blocks because I don't think having a pattern is the best approach because like I said, you've got to have a versatile approach to changing when you, you know, contact people. So when that first call block comes up, I'm still diving in, doing calls for an hour. My meetings usually are scheduled. I try to have one in the morning. I really love the 10 o'clock meeting. I feel like you're sharp, you're on your game. Game. And from the customer perspective, I feel like they've had the same opportunity to do that. You know, they get in, they get their desk clean, they get their email cleaned up, and they've got a real conscious sense of mind to sit down for a 10 o'clock meeting. And then I try to do another meeting in the afternoon, usually 2:30, 3 o'clock. And in between those 2 meetings… I say meeting, but they're not just generic meetings, and it's going to kind of dive into the next activity level of what we do… but we have what I call the twos. So every day, we have 2 revenue-generating opportunities. Those meetings are face-to-face meetings with the client, whether it's the discovery or their presentation, or it's a tier 1 partner meeting, you know, someone that's going to refer business to us, or it's a meeting with an existing customer, you know, doing some quarterly business reviews, doing some consulting for a customer. All of those activities, I want to do 2 of each of those every week, but I want to do 2 of those combined in any sort of ratio per day as well. One in the morning, one in the afternoon. And as long as I do 2 of those every day, we're going to hit those activity levels that we need to be at to find success. Awesome.

46:23 Scott Ingram: And then when are you determining… you said that there's not sort of a set structure to when the time blocks are. So when, when do you structure that? When, when do the blocks get put into the calendar?

46:36 Jack Wilson: Sure. So basically when you do any lead list building activity, you know, we don't actually use a lot of inbound tools, which I wish we could get to the point where we had a big enough reach where we were just getting a lot of inbound generation. Creation. But when we build our own lists, usually it's during that block that before you start to build the list, you have to know when you're going to tackle that work. So, you know, I schedule a block of time that says, hey, at 9 o'clock I'm going to sit down, I'm going to put together a list, I'm going to do my research. Before I start that, I know I'm scheduling those calls for, for example, Thursday at 3. I'll put that block in the calendar, and then every potential lead that we create that gets added to that list, we actually pre-schedule that call. So, you know, from 3 to 4, it's, you know, 3:01 to 3:02, call this company. And we actually pre-schedule all of those activities. So then whenever that block comes up in the calendar, you know it's coming up, you can prepare for it, you sit down and you just execute. Now we do the same on the back end, you know. So calling every… calling anybody once is a waste of time. If you're only… I tell my guys, if you're gonna call them once, don't call them at all. You know, that sweet spot between the 6 and 8 contact points where it's really going to lead to an appointment. So we have a cadence like most great sales organizations do, and part of that cadence is making sure you pre-schedule the follow-up activity. So during that call block hour, before it starts, we know, okay, if it's Thursday at 3 o'clock, I'm not going to call them on Thursday. I'm going to try to call them in the morning instead of the afternoon. So, you know, next Monday, you know, at 8 or at 9, that's when we're going to schedule that block for follow-up. And then all of those activities, when they get completed, they're going to prescheduled for that block that we've already set aside for ourselves. So very deliberate, very scheduled and planned through every step of that cadence.

48:19 Scott Ingram: Awesome. So that's probably a pretty good transition point to sort of how you've been coaching your team through structuring their activities and what those buckets are and what those expectations are. Sure, absolutely.

48:31 Jack Wilson: And this is where, this is where I'm really counterculture. And I think this is where the conversation you and I had before this really I think it shocked you, and correct me if I'm wrong, but I think when people hear these activity levels, they're going to say, how? How is that possible? Because they're low. And I want everyone to know that I'm not an advocate for not working hard. That's not what this is about. Instead, I'm an advocate for being hyper-efficient and being very targeted and very deliberate in how you spend your time and talent. So having said that, our activity levels, there's an easy-to-remember moniker. We call it the 2-4-6. 6, 8. So every day I mentioned the 2s. So we have to have 2 revenue-generating opportunities a day. The 2s are meeting with existing clients, it's meeting with tier 1 partners, it's assessment meetings, which is what we call our discovery process, and it's presentation meetings. So every week you have 2 of each of those, but within each day you want to have 2 total of any combination of those activities. So if you're doing an assessment in the morning and a pitch in the afternoon, there's your 2. Now in between the 2s, we've got the 4s. So the 4s is what we call networking activity. So networking could be your, your breakfast, your BNI groups, which, you know, are… that's a whole different animal. But your networking groups, your Chamber of Commerce, your trades professionals groups, your after-hours, you know, your networking groups and your expositions. 4 networking groups over the course of the week. So making sure that usually that's going to be once a day because at a 5-day workweek, I actually tell my, my team to take an admin day. And that's a very important part that I should have probably started with is I think having an admin day is very important because it takes the stress of making sure you're doing all those tasks that are going to be those time sucks that are going to make your blocks bleed longer. Having an entire day that you can dedicate to that administrative creative type, getting stuff done moments is important. So that's why the networking is 4, because it's 1 a day for those 4 days that you're in the field. So we go from the 2s to the 4s to the 6s. The 6s are actual walk-ins. So we do 6 walk-ins per day. And I think this is part of where people are going to get shocked by saying, well, that's not a lot. And it's not. That's why it has to be done right. They've got to be with highly targeted, highly targeted, qualified businesses that we know have a high likelihood to convert to an appointment and potentially a customer. So, and how you plan your day around that makes perfect sense. If you've got 2 meetings and you're doing 6 walk-ins, well, if you're doing 3 walk-ins just outside of those meetings, you can hit that 6 really easily. So over-indexing on those goals becomes even easier because if you're already doing what I think people… you leave a meeting, you hit a door to the left, to the right, and one in front of you… just by having your preset meetings, you're gonna hit your 6 walk-ins right away. So from the 6, we go to 8. 8 is our dials. 8, just 8 dials a day. And I know every SDR that's listening to this out there is, is thinking, if I could have a job where I only made 8 dials in a day, I would love it. And the reason 8 dials is so important is because I have a really counterculture methodology behind dials. I don't want to make 100 dials that might happen 1 or 2 times. I want my team to make 8 dials that I know that they're committed to dialing those same 8 prospects through the entire cadence. And it's not just dials, you know, they're gonna then bleed into other activities… your email outreach, your social outreach, and things like that. But those 8 leads, we're gonna follow those leads until they're really worked, until we really know, are they qualified or disqualified? And if they're disqualified, we kick them out, we refill it with a new lead. Or is this a potential opportunity that I really want to follow them through the lifecycle and make sure we work the lead until it's worked? So 2, 4, 6, 8, that's the, that's the activity plan I have for my team and myself. And before you think we're crazy, that's the activity plan that led to 223% growth in the book of business when I showed up day 1 at Cinch IT.

52:45 Scott Ingram: Well, and, and not only that, but, you know, the, the consistent execution by the rest of your team with everybody sort of being overplanned. I think, you know, one of the things that you talked about when in our first conversation was this idea that people talk about levels of activity that they're not doing every day. Like maybe they're making 100 dials, but they're probably only getting together the, the stamina to do that. Maybe that happens once a week. And I think the reality of your model is, one, it's achievable, but two, it's just the consistency. And it probably also negates out the fact… I mean, the thing that I see frequently, especially in a market like yours where you're going after the small business, right? There's a higher level of volume that you need to be achieving, right, to make your goals. People get into the kind of peak and valley sort of system where, oh shoot, I don't have enough deals. So they prospect their brains out and then they're working a whole bunch of deals and they don't have time to prospect and the cycle repeats, right? And so they're, they're having great months and then they're completely missing and going back and forth. And I think what's fascinating about your model is it has that built-in consistency where I don't imagine you have peaks and valleys in your business. It's probably really nice and consistent.

54:04 Jack Wilson: It's amazingly consistent. And I think one of the craziest parts is that it's really consistent across the different sales reps as well, you know. So the first 2 guys that joined my team are 2 very different sales professionals. You know, one of them comes from business-to-consumer sales. He was in the insurance industry, so he has some sales acumen. He's got some experience, and he's got a really, you know, Type A dominant driver, typical sales, you know, profile. And the other one of my sales professionals is really a high I. He's an influencer. He really cares about relationships. He's not an arm twister. You know, he really does develop rapport with clients, and no sales background. I mean, a little sales background in a retail sense, but not true outside business-to-business sales. Despite those different backgrounds, and then myself coming from banking and B2B sales, I did the math on our first years, relatively speaking. So if you took my first year and I lined it up with their first couple of months in their roles, we all produced at exactly the same clip, the same number of net new customers per month, and roughly around the same… we measure our success in users because it It really all depends in IT on the end user, who we're supporting. So the user counts and the net new relationships are all within a small margin of error, relatively the same for all of us. Now, does that mean that they're phenomenal salespeople like I was? Does that mean I'm not half as good of a salesperson as I thought I was? I think none of that is actually the case. I think it's like what you said. There's no peaks and valleys. There's just consistent true performance. Based on the numbers that we know to be real in our industry and our environment. And, you know, that's a very real thing. You know, you mentioned during our conversation about how people talk about the high levels of activity. As sales professionals, we're trained to shoot high, you know. So there was one of the episodes I was listening to that, you know, if your goal is, you know, X in revenue, you really want to… or your quota rather is, you know, $100,000 in revenue, you want to set your goal at $300,000. You want to set it 3x your quota. I think people do that with activity. So when you hear sales professionals talk about their activities, I think what they're telling you is, you know, how many calls do you do in a day, Scott? And you'll say, oh, 100 calls a day. I think that's the goal. So I think what we're hearing is people talking about their goals for activities in a day. But like you said, how often are they hitting the 100? You know, it's not that they're not doing them at all. They're probably more at 80 to 88. And SDRs is really different because they're tracked and they have to hit those goals. Goals, but from a quality perspective, you know, what was the consistent… consistency, sorry, in those calls? And what type of end prospects were you calling? How targeted was it? And we've taken the approach that it's quantity… or quality, rather, over quantity. And, and I'm finding that it's just as, if not even more successful, as, you know, beating it over the head and doing 100 dials a day. And, and it all comes back to that mental game and having your goals appear to be realistic and reasonable and achievable. You know, sales is a, is a big-time mental game, and it's a lot about mojo, you know. And especially in the SDR world, if, you know, your goal is 100 dials a day, burnout happens. And you could tell by industry statistics, you know, that the lifespan of an SDR, it's a short window. So rather than burning out, you know, my guys, I want them to have goals that they think are realistic But I've also got to make sure that they're going to meet our bottom line and our needs. But at the end of the day, their mindset is positive. They know they can achieve these activities and the numbers always prove themselves to be true. So that positive reinforcement that they get by following a process that works and works consistently is even more rewarding than just slugging away, you know, 45, 50 hours a week trying to hit those goals. Yeah.

57:48 Scott Ingram: Well, let's, let's dig a little bit deeper into the quality and particularly on the front end, because I have to imagine that part of what's making this work is you are very targeted about what goes into kind of the cadence and who are we going to target. And it's less about the spray and pray, which is probably what improves the throughput and the numbers that you see on the back end.

58:12 Jack Wilson: Yeah, absolutely. And the easiest way to define that is not actually by saying who do we want. A lot of times the easier way is by defining, well, who don't we want? And I've been guilty for a long time of, you know, the answer for me is always yes. If I… I always think that I can convert something into an opportunity, especially if it makes sense. I can fit… you know, it doesn't have to be a square peg, but I can fit an oblong peg into a round hole. I know I can. And that's a losing mentality, because if you really… you look at your, your time and your skills and your talent, you're wasting those hours on opportunities that aren't likely to convert real quick. So it's quickly identifying what types of opportunities you don't want, what types of prospects aren't going to be a good fit. And it sounds selfish in the approach. But at the end of the day, it's all about the customer, you know. And if you're reaching out to clients that aren't going to be a great fit, it's not just your own time that you're wasting, you're wasting their time as well. So it's, it's really out of abundance of respect for your prospects to not reach out to the ones that you don't think are going to be a fit. So we do a really good job early on explaining what's an opportunity to walk away from and being okay with walking away from an opportunity. I think one of the most empowering feelings when you're in sales is being able to say no. You know, I tell my entire team every day, you don't need any sales. You don't need a sale. You sure do want them. You really want them, but you don't need them because the moment you need the sale, you start behaving outside of your normal activities and you start doing things that aren't going to benefit yourself or the customer. So all the way back to the prospecting level, it's understanding Understand what types of customers are best fits and use yourself as a model. Take a look at your current existing book of business. Find out the outliers. If I have a high percentage of manufacturers, for example, I want to target those manufacturers. What are the user counts on average that result in positive relationships and how can I focus on those? And then when you build your leads list, just before going and executing on that leads list, do one more run-through. To yourself, if I look at this prospect, is there a moment in my head where I'm going, it might not be a good fit? The second you have that question, take them out. Don't, don't spend time on something that might not be a good fit. Make sure it's 100% a fit and you know you're gonna dedicate yourself, because over the next, you know, week, 2 weeks in that cadence, the amount of effort you're gonna put into it, make sure you can get out of it the same that you put in.

1:00:37 Scott Ingram: That's awesome. And I think there's, there's so much to, you know, what you said. I mean, not just, not just kind of the overarching theme I think we've been digging into in terms of the consistency and the measurability and the activity activities and those things, but it's, it's the psychology and putting, putting folks and yourself in a position where you feel like, I'm winning and I'm good at what I do. And, and, and also that just that idea of not needing a sale, I think that leads to all kinds of, of bad behaviors. Desperation is never a good thing in a sales professional.

1:01:08 Jack Wilson: Never. No, absolutely not. And, you know, I try to tell my team every day, you know, you know, we'll have check-in calls and one of the guys today was just rough. It was one of those days, you know, the gatekeepers were beating me up, or, you know, I felt like I was getting walked out. And I always say to them, I said, what do you mean? Today was just a day. And every single day in sales, it's just a day. Why? Because it's not, it's not what happened during those calls that matters. That's not how you judge your day. How we judge our day is, did you do the 2-4-6-8? If you put in the level of activity that you know is gonna lead to success, you might not have got ink on paper today, you might have not I got a sale today, but you know that, that, that effect of the exponential growth of your pipeline and that cumulative effect of putting in that activity, you're going to win a month from now. And that day that you won, it's going to be because of the activity you put in today. And there's actually been, you know, a few days that he calls me up, you know, that same rep said, man, it was a great day, a lot of great conversations. And even on the positive side of it, said it was just just a day, you know, and I do want to celebrate victories. You've got to have that positive mindset. But hey, it's just a day, you know, when we get the closed deal and we get the new customer, we'll really celebrate that. And we'll go back and we'll actually look at what was the activity that you put in. And I'll do actual… I call them audits. I hate the word audit, but I do audits on their cadence. And I think a really powerful moment actually happened earlier this year where my first sales rep that I hired on the team, I actually made him go through every level of being a sales professional. So he started as sales support for me, and then he migrated really quickly… I'm talking in a month's time… to inside sales. So he started doing outbound dials to book appointments, and then from outbound dials booking appointments for me, started booking them for himself, then he started going on them, and then he became a field rep. So we got an inbound call from a potential customer that said, you know, they're not happy with their current IT provider, they're really looking for an alternative solution, they'd love to meet. So I booked it. I took the call, I booked the appointment, and I look back to our CRM CRM tool, and lo and behold, this sales rep had called them earlier on in the year, but he had stopped in the cadence before he hit 6 to 8. So this is one of those moments where he didn't hit that activity level. And you know, it was about February when he stopped calling. Now, when we met with the customer, he said to us, "Yeah, in March I had an issue with my current provider, and I really looked to change." So that coaching moment was: if you stuck to the process and you just followed you the, the process that you know works and you called them back, you would have uncovered at that very moment the pain that led to the appointment. So even though it wasn't positive reinforcement, it was a real aha moment that said, man, I don't have to call a ton of people. I just have to call the right ones, be consistent, and stay on top of it because those opportunities will present themselves. So those moments are few and far between now, Because he sees the value of making sure that once someone is in the pipeline, you've got to put your full effort and will behind it. So be very selective before you put them in, but then once they're in there, stick to it and make sure you're working the lead until it's really worked.

1:04:16 Scott Ingram: Yeah. Now, what do you find to be the biggest challenge with this sort of process and approach?

1:04:21 Jack Wilson: Keeping people positive when, when there's a perceived slump. You know, if you go through a period of time where, you know, maybe you've got a larger client on the hook and the sales cycle was a little longer and you're not seeing the results results, you know, making sure to keep that positive attitude because, you know, when they're thinking, okay, where's the next deal coming from? If they're not doing 100 dials a day, maybe you don't feel like you're working hard enough toward it. So it's just keeping folks positive when the lulls happen and, you know, teaching them a lot of times about planning for those things. You know, holiday season, we're in the thick of it now, making sure that you're over-indexing for the days you have off. You know, just because you don't work a day doesn't mean that those numbers change. I think that's very important. You know, we had one meeting where one of the reps, you know, we always do like a ratio, like, you know, 10 over 20 calls, your goal is 20, you hit 10. And we had a meeting on a week where there was a holiday and his goal number went down. I was like, well, wait a minute, how come the goal number is down? He's like, oh, well, you know, it was Thanksgiving. Well, I understand that it was Thanksgiving, but does it change the fact that you still have to make that amount of dials to get an appointment? So you lost a day. That's one of those instances you have to put in a little more work, you have to over-index for the time you lost, or you have to spread that out evenly over the rest of your days. I think tackling goals in small chunks is very important, going back to the psychology of sales. If I fall behind on dials by 30 dials, 30 is a big number. That's like a chunk of dials. It's a session that I'm going to sit down and have to crank out dials. But if I'm spreading those 30 dials out over 3 days or more, that's 8 to 10 dials a day. That's a manageable, reasonable chunk. So taking that kind of Thanksgiving example or the holidays that are coming up and saying, hey, I'm gonna lose a day here, it doesn't mean I have to do all 100 of those dials in one day. Let's spread them out over that week and make sure my levels only incrementally increase on a day-to-day, but I'm doing enough to make sure to recover for that loss of time.

1:06:19 Scott Ingram: Well, and so what does that mean for sort of your goal-setting process? When… and in particular, what are the intervals that you're typically thinking about when you think about those goals.

1:06:29 Jack Wilson: So when you say an interval, where are you looking at measurements of like revenues, relationships? Kind of where is your mind at behind that?

1:06:36 Scott Ingram: Well, so 2 pieces, right? So one, one is that, but in terms of the interval I'm talking about, is it a weekly goal? Is it a monthly goal? Is it a daily goal?

1:06:45 Jack Wilson: So we have… we basically go month to month, and we actually have what we call an escalator, which is a little different in sales. So every month, you know, your quota is set at a particular level, but the next month it's going to increase by an escalator. And every month month, their quota increases right now by the same escalator. So everything that we do is recurring revenue. So when you bring on a new relationship, you know, that, that sale is going to produce revenue next month and the next month and the next month. So, you know, that escalator, as long as you're selling the right way and you're bringing in relationships, it doesn't become a problem. But if you fall behind that, it could be a challenge. So coaching folks to, to stay focused on the short term, month to month, is important. But we also have a quarterly goal as well. So we do have, like, you know, on the commission and incentive side, we have a SPIFF for hitting quarterly goals as well. So it's month to month, and then another check-in at the quarter. And then obviously annually, you know, we want to make sure that their goal for the year they're hitting as well. Got it.

1:07:43 Scott Ingram: And what about your sales philosophy? Is there sort of a particular approach that you subscribe to?

1:07:50 Jack Wilson: We actually have our own process that we developed in-house. And I guess my philosophy really is to follow that sales process. And we have a 2-part process. Process where the discovery is a little more than just your average discovery. We're actually producing value on our discoveries. We do cybersecurity audits for clients right up front. So we're going to come back on a presentation meeting and actually give them a deliverable, give them a service basically for free throughout our process of, of kind of the sales cycle. But the philosophy behind that is I always want to be valuable to a client, you know, whether it's, whether it's a fit or not. I want to make sure that by taking the time of their day, I'm truly adding And it's not adding value just by doing whatever it is that my service or product is. I want to add value by having a deep dive conversation and really educating them on things that they don't know about. So part of that philosophy also is, is honestly being very okay with walking away from an opportunity because it's not a good fit. And I try to coach my entire team that when you get to that moment that you say, you know, maybe it's not a good fit, I want you to be comfortable telling that client, this process was great. I hope you saw that it was valuable, but at the end of the day, I don't think it's a great fit, and here's why. And being okay with walking away from that. So it's not, it's not selling anything to someone that they don't need. It's not fitting square pegs into round holes. It's, it's being honest and upfront with your customer and being honest upfront with yourself. That's the real philosophy I try to live by.

1:09:17 Scott Ingram: Awesome. And then how would you describe your style in the way that you execute that philosophy?

1:09:22 Jack Wilson: Boy, style is a… style is a loaded one. I'm a very relationship-based salesperson, which I think has turned into like a 4-letter word nowadays. You know, we're in the era of the challenger sale. And, you know, if you're building too much relationship, you're not closing enough. But I truly believe that, you know, if you develop a sound relationship and you put your clients' priorities and needs almost in front of your own, you know, the whole giver's gain philosophy is really going to come to light. So I try to develop really strong relationships with my clients and really understand what it is that drives them. And that's sort of my approach to that.

1:09:54 Scott Ingram: And how do you, how do you sort of look at and coach through the different styles amongst your team? Because I'm sure they're not all one wired like you? No way.

1:10:03 Jack Wilson: And that's the, that's the most fun about actually leading a group of individuals is, is understanding that there's, there's different styles, there's different mindsets and characteristic types. So I actually don't have a blanket leadership process. What I try to do is I really sit with each individual on the team and find out what's their why, you know, what is, what is the driving force behind them? What motivates them in life? And it could be a goal. It could be somewhere they're trying to get, but I really want want to get even deeper than that. You know, what is it they care about the most? You know, why are they here at Cinch IT? And, and how do the goals of Cinch IT align with their individual why? And I actually don't really set… I don't set goals for my sales team. It's going to sound strange, but I set quota. My sales team sets their own goals, and my job is to really enable them to figure out what those goals are and why they want to achieve those goals, and then to help them reverse engineer their way to So I individually meet with all of them on a regular basis to hold them accountable to their own goal. Because I really do believe, you know, just like my career, I didn't have a manager and I had to just be successful for myself. If you can find that motivation within yourself, you could find the reason why you want to find success and you can align that with the company that you work for. That's when you're going to be the best version of yourself as a sales professional. So as a leader, I try my best not to take any blanket approaches. I try to be hyper-individualized, which, you know, a lot of leaders listening will probably think, well, you can't do that when you have a large team. But I think it's absolutely possible. Everyone has check-ins and one-to-ones with all their individuals. And it's really easy for us to take the same message because it's repeatable and just deliver it over and over and over again. But I would challenge leaders out there to really be specific. And treat, you know, if you just treat your sales team like a customer through a discovery process, it's really no different. Finding out what makes them tick, what's their buying signals, you know, what are some of the objections you have to overcome and handling those objections. At the end of that whole transaction on the sales side, if you take that analogy to coaching a salesperson, at the end of that whole sales process, the outcome is a close. You've gained their buy-in and that buy-in is the mission and the goals of an organization and the opportunity for your success and their success really to be in alignment, which is a powerful thing.

1:12:21 Scott Ingram: Well, and one of the things I've really been wanting to dig into a lot lately, and I think you're in a great position to offer some advice and suggestions here, is how do you do your due diligence around and sort of qualify around a leader, right? If you're evaluating a new opportunity or a new role, right, and you're… I think that there's so… the criticality of the individual that you're working for and with has such a big impact on those results. What would you suggest that people do to sort of flush out whether or not that's going to be the right fit and whether that's going to be an enabler or a detractor?

1:12:59 Jack Wilson: Honestly, I think it's getting outside of your comfort zone. And sometimes what, what feels like the wrong fit could be the best fit for you. You know, I want my leader to be nothing like me? Because what I really want from a leader is, you know, someone that's going to be… that they're going to fight for me, they're gonna, they're gonna have my back, they're gonna make sure that my success is their top priority and not their own. You know, that's the first one, is are they leading because they want to hit their goal, or are they leading because they want everyone to hit their goal? That's a… and that's a tough thing to flush out in conversation, but, but kind of, you, you can really figure out where someone's priorities at because, you know, you can see it in a leader when they lead from behind. That's really, hey, I'm behind my goal. I need to get there for me. So that's a, that's a big thing is making sure everyone else's goals are before theirs. But besides that, I want to, I want a leader that is nothing like me because I want them to add to my character, to my personality, to my skill, my sales skills in ways that I probably didn't even understand. Because if they know what I know and we're doing a lot of the same things, the chances for growth are going to be limited. So I want to make sure that they have a background and approach that's going to be a little bit different than mine so that I can probably pick up those new skills from them. And, You know, in my company today, you know, the owner of our company is a retired Army Ranger. He's a very structured, you know, Type A dominant driver, and he drives the ship. And that's very important because he's, he's got, you know, outcomes for the company in mind and he's working on, you know, in the company or sorry, on the company rather than in the company. But his way that he leads is to still give me the flexibility to do what I see is going to achieve those goals. So although he's driving and he's making it clear what those end outcomes are, he's allowing me to craft the way I achieve those outcomes. And I actually want that for my sales team as well. I want to be the leader that even though we have a system, the system can't be black and white. It has to be customizable. You've got to be able to plug in your own personality, your own day-to-day, and honestly, it's your own numbers. You know, if someone's good at one thing and not the other, it's understanding that and adjusting your process, you know, in that manner. So making sure they have the flexibility to let you lead or behave in the way that you think is going to be successful, as long as they can hold you accountable to that in the end. Yeah, awesome.

1:15:20 Scott Ingram: Now, what motivates you, and how do you think about motivation in general?

1:15:25 Jack Wilson: This is going to be the worst answer ever, but I still don't know. I, you know, every single day I ask myself, what is my why? And at the end of the day, I think it's really… it's not a result It's it's the journey. So motivation can be an end goal. It could be something you're striving toward, or motivation can be sort of that burning flame. And I just have a passion for for really being successful. I love to apply myself to a challenge and and to make it happen and to do it the best I possibly can. And it's funny because it's not it's not motivation through through reward of money, through recognition. It's just understanding that I can apply. Myself to a problem, to a challenge, to a goal, and I can see that outcome. And seeing that outcome and seeing my impact on that is really what drives me. I love to know that I'm part of something bigger, that I can achieve something, and that I'm tangibly impacting, uh, you know, the people around me, not just the people that work for me, but my customers, other people in the organization. Everything that I do, it's really got less to do with me than it does with everybody else that, that is a part of that. And, and that's a really motivating That's awesome.

1:16:36 Scott Ingram: I think that's a better answer than you think. Thank you. So, Jack, is there something… I mean, and we've covered some of these already, but I wonder if there's another one. Is there something you believe that the average sales professional would think is crazy?

1:16:50 Jack Wilson: Honestly, it's that you don't actually have to work all that hard to be successful. And I'm not saying to be lazy, and I'm not saying to tone it down and not put in hard work. Hard work. But at the end of the day, I hear so many people that say, oh, you know, I'm working this many hours, or I'm breaking my back. And, and you hear about the way that that impacts their, their personal life. And I, I truly am an evangelist for, for work-life barriers. I, I don't think work-life balance is a real thing because balance indicates to me sort of like a homeostasis or an equilibrium. And just by the design of how we work, you know, it's a 5-day workweek. And by the nature of it, you're spending more time in your profession than you are in your own life. So there's really no such thing as work-life balance. So the work-life barrier, the work-life border, I think is very important. It's something I try every day to really hold true to. You know, when you get home and you decided my work for the day is done, really trying to, to leave the cell phone on the table, to not check emails too much and, you know, to not dive back into it. And honestly, even not to talk too much about it, you know, at home. You know, you've got to get home, you got to flush it out, but let's really just move on and enjoy our personal life and set a boundary between the two of those things. And that the happier you are in your personal life, you know, the happier you are in your work life and vice versa. So really taking the same amount of time and effort you put into your craft and your profession to, you know, improving yourself as an individual, as a family. And, you know, I don't have kids yet, and I hear, you know, a lot of the folks on the podcast talk about being successful and having a family, and that thought terrifies me. I'm not sure how I'm going to find the time to do that. So, I think that's going to be the next great challenge and motivator in my life.

1:18:33 Scott Ingram: Yeah, that's awesome. Well, and I think there's really been a recent theme of this idea, and you've touched on it at some level too, is just this idea of focus, right? There's so many distractions in the world today, but if you focus on the thing that you're doing at that point, right? If you're doing a call call block, make calls, right? Don't check email. Don't worry about social. Just do that, right? And I think on the flip side, even on the personal side, right, if you're with your family, be with your family, right? That's not the time to be checking your phone every 5 minutes. I mean, something that I've been personally working on real hard, and I think I was actually moderately successful with that in our Thanksgiving little Dubai trip, where I just put everything aside and said, look, I'm halfway around the world. There's nothing I can do to help you So, here are the other resources that are going to take care of you while I'm out, and I'm going to go just be with my family. And I think that makes a big difference. And now I'm trying to bring that back into just the day-to-day, right? How do you apply that in the work that you're doing? When you're in a meeting, are you in that meeting? And are you with that client or with that prospect? I think there's so much opportunity in that. So, what about the flip side? Is there something that the average sales professional believes that you you think is crazy?

1:19:45 Jack Wilson: The average sales professional believes that I think is crazy, and I think it goes back to that activity level. I think the average salespeople, or most salespeople, think if you just put up these gaudy numbers of activities, like 100 dials in a day, that no matter what, they're going to be successful. And when you say average, think about what that means. It's an aggregation of most of them, and I actually have a term that I use with my sales team. I call it most salespeople. Salespeople. So every example that I give them that I don't want them to do, we literally call it most salespeople. And I've had, you know, one of the guys on my team say to me, he's like, oh yeah, most salespeople do that. And it's become sort of like a moniker. And, and it's not to say that sales as an industry has a problem. I don't think that's the case. But I think that now, especially through podcasts like yours, we're really turning sales into the noble profession that it is. I don't believe that sales is 4-letter word. But I think, you know, a lot of, a lot of people still do. You know, they'll answer, oh, what do you do for a living? I'm in sales. No, no, if you ask me what I do for a living, I'm a sales professional. And, and what that means to me is that I'm able to have really deep, thought-provoking conversations with folks to uncover areas of opportunity where I can improve their lives. And that's what sales should be. But I think most salespeople's attitude is just, you know, they're plugging away trying to get the next deal. And, and I don't, I don't think that mindset that really resonates with me. I think it's a noble career, and I really do believe that.

1:21:12 Scott Ingram: Awesome. Well, let's transition that into the advice that you would give to somebody that's just starting out in a sales career today and wants to treat it as a profession.

1:21:21 Jack Wilson: Be vulnerable. I think the biggest part about entering a sales career is there's a lot of unknowns. There's a lot of uncomfortable things that you're gonna have to do if you want to be successful. So don't be afraid of those things, but be vulnerable. Vulnerable. As honest as you are with yourself, be with your leader. I think the best moment you can have is when you can really, really be hard on someone, be very specific about a behavior that they're doing, and have them take that not as criticism, but really chew on it and understand what it means and try to adjust that behavior and change it into something that's going to be successful. I talked about role play at the beginning. I don't think anyone loves role play. I hated it. I'd sit in a training room and they'd say, oh, we're going to role play, and my palms would sweat. I'd get that flush of heat. Like, I hate roleplay, but then when I did it, I'd be, I'd be great at it. So why do I have this resistance to something that's uncomfortable? And I think when you're entering a sales career, you have that about a lot of things. And, you know, sometimes it starts with picking up the phone. And if you just do the activity and you apply yourself to it, you allow yourself to get uncomfortable, you allow yourself to be vulnerable. Uh, that's very important. You know, I resisted the, the ride-alongs with my managers way back in my career, I would try to come up with every excuse of why it wouldn't happen. You know, a meeting canceled, it got pushed out. Like, I didn't want to be observed. And sometimes I listen nowadays to these tools. I hear a lot about Gong.io and how people can listen to a call, a sales call. And even now, sometimes I catch myself thinking, oh, I would hate that. But you can't have that resistance because these tools are all designed to help you improve yourself. So turn off that, you know, turn off that ego, turn off that, that outer shell and that defense mechanism to really allow yourself to be vulnerable, to boil yourself down to your basic premise in order to build yourself back up as the best version of yourself that you can be. Yeah.

1:23:14 Scott Ingram: Well, and it sounds like you're having some good success on the phone. What advice do you have on that front in terms of being good and just making a successful cold dial?

1:23:24 Jack Wilson: Throw every script you've ever had in the trash. That's another big counterculture thing that I believe in. Your script is for you, and your script is for you to practice. And, you know, if you, if you want to use a script, use it in the mirror, you know, use it on yourself, leave yourself a voicemail, do it 100 times until you, until you understand the words that are in that script, until you understand why you're saying it and what the impact of those words have on the client, and you internalize it. Only when you've internalized what you want to say, throw away the script and get on the phone because it has to be natural. I really believe in the power of intent. So when you pick up the phone and you're calling a prospect, what is your intent? Well, if your intent is I'm going to read this script and I'm going to do a damn good job at it, and I'm really going to deliver these lines, what happens? Let me ask you, when the script is over, what happens when that client actually engages with you? You know how many, how many people get through a gatekeeper and they get to decision maker and all of a sudden, oh no, now I don't know what to say because I don't have a script. It's because you haven't internalized it yet. So when it comes to being on the phone, you know, you… I'm sure you've heard the whole be human, don't be a robot. It goes a step further than that. It's really internalize what you want to say to a client. And in my approach, when I do a prospecting dial, and I'll be 100% honest all of the time, I'll pick up the phone and say, listen, I've really been trying get a hold of you because I would love to do business with you. You're the type of business that I've been able to… and then insert your value props, but insert the value props you believe in. You know, how have you fundamentally transformed a customer through the service or product that you provide? And if you believe in it, your intent is going to come through and they can hear that. So make sure your intent's not reading off that script. Internalize it. Throw the script away before you pick up the phone. Say to yourself, what's my intention here? You know, am I calling to book the appointment? Am I calling to learn some more information about them? Am I calling just to get, you know, the name of who that person is that I need to call? And, and really understand and deliver on that intent. And, uh, I think the fear of the phone goes away.

1:25:24 Scott Ingram: Awesome, awesome, awesome. So typically I ask sort of the advice that you would give to somebody that's kind of mid-stage, right? So they're, they're into their career, they're good, but they're, they're maybe not great. Although I want to flip it for you and, and ask, and, and ask what advice would would you give for most salespeople since that's how you refer to them?

1:25:43 Jack Wilson: Yeah. And see, now I feel like that's a 4-letter word. I feel, I'm feeling a little bad about it. For most salespeople, right? You could look at where you are in your career and that might be okay. You know, wherever you are in your career, being a top 1%, you know, producer isn't for everybody. So understanding those strengths and weaknesses internally is important as well. So for most salespeople, figure out, are you most salespeople? You know, turn around, look, look internally, reflect on yourself and say to yourself, if I'm here now, I'm middling in my performance. It's, you know, it's where I need to be to keep the job. It's not where I need to be to get that next opportunity. Are you comfortable being where you are for the next 5, 10, 15 years? Because in sales, tenures usually aren't that long. And you could find great salespeople that are in those tenured roles, but it's because they had that moment where they realized, I don't want to be a top 1% producer. I want to be really good at what I do. I want to go to work every day and be happy. I want to have that work-life boundary. If that's you, it's actually fine. Turn your attention to honing your craft and doing it better. You know, it's will over skill. So if the will isn't there to go to the next level, there's another way to do it. And it's by honing your craft and becoming even better at what you're doing today. So at least challenge yourself to improve on the skill side of it and to, to really get good and better at what you do. That's what I, you know, what I always try to do is what's the end goal here? And I've been very bad at being a career planner. You know, we talked about my background. It's been like targets of opportunity. It's… but it's because I did a really good job at what I was doing at that moment. Those doors always open for yourself. Well, if you're most salespeople, those doors aren't just going to open themselves. So you have to be a little bit more deliberate about your career and obtaining skills that you need and understanding really where you want to go with your career and having a plan around it.

1:27:37 Scott Ingram: Yeah, love that. And this, this whole like honing your craft thing for me is to… I feel like that's what it all boils down to. And I love, I love your will over skill idea, right? And, and frankly, I think that if, if you're still listening to this and you're listening to a 90-minute podcast, You have that, right? You have the interest and the desire to learn this and figure this out and to improve yourself and to really treat this as a profession. And that's who I built the show for. And it's why I do it myself, right? This, this helps me improve in my day-to-day role. Jack, what, what's the thing that you would want to know about other top sellers in other organizations? Sure.

1:28:17 Jack Wilson: I think it's just really knowing how they organize their day, you know, how they plan their day. And, you know, this whole conversation started started with, like you said, that the challenge… if someone's working less than, you know, 40 hours a week and they're a top producer, I want to hear from them. I want to hear from those top producers how much effort you are putting in. A lot of times I think, you know, if they're consistent producers, I, I think they've got to a point where it levels out. I'd love to see what those days look like. I always wonder, do I do enough? You know, could I see meteoric growth beyond where I am, even more so if I applied myself not maybe more, but differently. You know, what's the approaches that they take to cut out some of those distractions? How do they stay focused and things like that? That's what I'd love to see from some of those top producers. Yeah, love it.

1:29:03 Scott Ingram: And one of the things I think we will figure out how to build into the agenda for the next Sales Success Summit is really that idea is structuring days, building process, right? So how do you build your own sales process, but also how do you build your own time plan and structure your day and structure your time so that you can be be efficient because I think in a lot of ways what you've achieved and what you're achieving with your team is what we all want. How do I get great results but be efficient, be effective, and still get to have a life? Like, I don't want to kill myself to have this, right? I want to be able to enjoy the fruits of my labor. You told me a story, and I don't know if you're willing to share it publicly, about the thing that sort of prompted this and something that happened at it was a President's Club or something like that.

1:29:53 Jack Wilson: Are you open to that? Absolutely. Yeah, that was a, it was a really eye-opening moment. And it, you know, when I told my story about kind of year between years 2 and 3, you know, there definitely was a time where the activity level bumped up a little bit. And I was, I was approaching that threshold where I thought, I'm putting a lot into this. I don't want to, I don't want to have to keep putting this amount of effort if it means staying at the top. So I almost ended up in that most salespeople conversation. Well, do I have to be be number 1, or can I tone it down a little bit, be number 10, and still be happy with my life? And what prompted a lot of that was, like you said, I actually had qualified for… they called it Citizens of Excellence… and I was on the trip, and I ranked number 4 that year. And to me, it was a huge failure because I wanted number 1. But at the end of the day, the top 12 went on the trip. So whether it was 1 through 12, you're still there and you're still recognized. So that was the first moment of realizing you don't have to be number 1. Being number 4 is pretty damn good. I'm on the trip and I looked in the back corner of this hotel. There was like a patio where you could go eat your breakfast on. And in the very far corner of the patio, I see a gentleman from the company alone on his cell phone, you know, talking feverishly on his cell phone. It doesn't take a genius to realize this guy's working on a deal. He's like talking to a customer here. Now the trip involved family, so you got to bring a plus one. I brought my wife and most people brought their significant others or somebody that helped them achieve their goal. And here this guy is and he's alone. And I had always seen his name in the rankings and every year consistently a top performer and always in that top 10. And I said, that's one of the guys that I want to go talk to and I want to learn more from him and figure out what he does to be so successful. And there he is at this hotel in the corner alone taking a call. And when he was done with the call, I went out to him and I said, hey, you know, what are you doing out here? And he's like, you know, you got to always be on your phone. You always got to be available to customers. Customers. You know, sometimes I'll… it'll be a weekend and I'm mowing my lawn on the ride-on lawnmower and I'm on the phone with a client trying to get a deal done. And, and I kind of had an epiphany. I said, well, wait a minute, he's, you know, ranked number 8. Here I am at number 4, and I think I'm doing half as much as him, but I feel like I'm, I'm 10 times happier. And that's the way I want to live my life forever. And that's, that's really what spurred this whole model and this whole process to be successful while having that boundary and making sure that you're happy while doing it.

1:32:22 Scott Ingram: Love it, love it. We probably should have opened with that like an hour and a half ago. Great stuff. Well, Jack, so the, the thing I try and do is, is we've talked about a lot, and I, I think this is one of those episodes that is probably worth listening to more than once. There's, there's a lot of gold in here, but I like to sort of break it down and, and create something actionable for the person listening to this that they can use to improve themselves over the, over the course of the next week or 2, what would you challenge them to do?

1:32:51 Jack Wilson: Yeah, do the math. So look at your results from the most recent period of time and start to reverse engineer your success. You know, there's, there's definitely luck involved with it, so try to take out those outliers of the lucky wins and really look at your self-sourced, you know, business and wins that you had and try to reverse engineer the math of what was the initial effort and activity that went into that and figure out what your own ratio are, because I think a lot of folks talk about doing that, but they don't actually know, you know. So you should know cold, hey, how many dials does it take for you to get on a… get on an appointment with somebody? Know your own numbers, know your own metrics. Even if you're wildly successful and you've been winging it, you know, for the whole time, if you take this approach and you look at this methodology, you might even be able to tone down some of that effort and get the same or better results. So if you're… if you find yourself in that position where you're working really, really hard, it's starting to come up on that border of, of being happy and being successful at the same time, truly take the time to do the math, figure out the numbers, and to take a fresh look at how, you know, potentially you can change your work in order to impact your life. Such great stuff, Jack.

1:34:07 Scott Ingram: Thank you for taking your… the time sharing all of this wisdom. I am really excited about, I think, what you've kicked off here as a core conversation that we're probably going to take into the summit. I'm so stoked about what that's going to look like this year. And it's not just the content. Of course, we will have great presentations and things like that, but I'm very intentional about the way that we build that event so that there, one, it's very intimate. We will have a maximum of 200 people. So, it's not going to be this overblown, you know, tons of people on uncomfortable chairs in a giant ballroom. Instead, it's about connecting. Connecting and building these relationships and helping to improve each other. So I hope you'll go check out top1summit.com, go find the details, get registered. The sooner you do it, the better that deal is. And I don't play any of the games, right? Like, this is about making an investment in yourself. So there's not going to be the Cyber Monday deal, the flash sale, anything else. Like, the numbers are the numbers, right? If you're either committed to yourself in your own improvement and performance and being a part of this, or you're not, and that's fine. So that's, that's what that's all about. top1summit.com. Would love to see you there. Jack, this has been incredible. Thanks again.

1:35:21 Jack Wilson: Thank you so much for having me. It's been an absolute pleasure, and I wish you the best of success, and everybody listening the same. Good luck out there. Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and for an invitation into our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.