158: Mentors, Grit, & Cultivating An Ownership Mindset with Zencity's Jack English

0:08 Scott Ingram: 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.

0:24 Scott Ingram: Today on the Sales Success Stories podcast, my guest is Jack English. Jack is the top-performing AE at Zencity and was a top SDR Before that, welcome to the show, Jack.

0:33 Jack English: Awesome. Great to be here, Scott. Thank you so much for the invite.

0:35 Scott Ingram: Yeah, absolutely. Looking forward to digging into this. And like we always do, right? This show is about interviewing number one top one percent individual contributors like yourself. And I'd like to jump in with some immediate value and talk about the top three things that you believe have contributed the most to your success in sales. What are those?

0:54 Jack English: Let's do it. So the reason I think I'm on the podcast is I'm on a little bit of a younger side. So I see my position here to kind of help some of those folks maybe at the earlier stage of their career figure out. Some of those, yeah, I guess those key success factors to help them launch super quickly to where they want to be. And for me, really simple. A, finding mentors. So identifying really early on in my career, the specific individuals that had that mixture of not only willingness to engage and shape my behavior and my sales outcomes, but also have influence within the organization. And then C, obviously just being great sellers that I could actually directly learn from and copy. Number 2 is the 80/20 rule. It seems a little bit obvious and I'm sure a lot of people have heard of it, but basically what it boils down to is 80% of the outcome and really anything in the world can be boiled down to just 20% of the inputs. And in a sales perspective or in a sales context, that can be really powerful if you leverage that correctly. So looking forward massively to digging into that today. And then the third piece of the puzzle here, I think as well, really important for younger sellers is to take ownership. A little bit of an obvious one, but I see a lot of folks, especially early on in their career, lack ownership over their output. And if you lack ownership over your output, then you're ultimately losing control of your outcomes. You know, my boss gave me the sequence to send out, the company gave me this or that to use. And as a result, when necessarily it doesn't work, we can kind of feel powerless to change our situation. So from day one, taking ownership and saying, hey, my number's my number and I'm gonna do whatever it takes to achieve that.

2:16 Scott Ingram: Perfect. Perfect. So I think obviously lots of interest for young sellers. You're quite early in your career, but I think a lot of these points are pretty universally applicable. Let's talk about the mentoring thing a little bit more first, right? Because the way you describe this, it sounds like you're primarily focusing on finding those mentors inside your organization. Is that accurate?

2:35 Jack English: Totally. So I think it's about looking at someone that's not only been there and done it, but also people that have key leadership characteristics. And naturally, just based on your environment, they're probably going to be inside your company. And I think that's interesting because, you know, there's people in, let's say, designated leadership positions who actually lack real leadership. And then everyday, let's say, quota-carrying individual contributors who have those characteristics in spades. And for me, there's really been 3 mentors and they've each, I guess, taught me 3 very important lessons about myself and about, how should I say, living up or performing highly in a corporate environment. The first one was my first BDR job. I was so desperate. I was really starving to be successful that I often let a more selfish side out of me. And that manifested whether I was dealing not only sometimes, you know, that desperation when you're dealing with prospects, but also even individually or excuse me, internally. With colleagues and other BDRs. And when a decision doesn't go your way, letting your emotions get the better of you. And had an amazing mentor. She's actually, Rachel, now teaching yoga and healing in Central America, which is kind of on brand for her. She showed me that even in the corporate world, that level of empathy and understanding is everything. The second mentor I had, a guy called Eric. Eric was only around 27, 28 years old. He was an AE. He took me under his wing, but he really had the head on the shoulders of, let's say, a 50-year-old. And he taught me the importance of professionalism. He, you know, only being 27, 28, always rocked up to a meeting fully on point. Everything was in place.

4:00 Scott Ingram: He…

4:00 Jack English: there was never a moment where, you know, you caught him kind of with his pants down. He didn't have the deck ready or he didn't look perfect. He's the consummate professional, buttoned up, doesn't accept lapses in concentration or silly errors. And that's so important, especially early on in your career, because oftentimes you're exhibiting behaviors that you don't even realize are maybe being a little bit unprofessional. And now you know that even the smallest absent-minded mistake can result in a massive drop in credibility in front of executive buyers. So learning the lesson of professionalism was, was really important. And then the third mentor that was really important was actually my current manager, a guy called Bar. I could do a whole episode on this guy, but the lesson from Bar is energy and teamwork, and energy is everything. How you show up to a call is in direct proportion to how the prospect is gonna react and actually perceive you and your company. You know, if you join the call smiling, interested in your prospect, genuinely excited, it's actually really difficult just from a human perspective not to reciprocate some of that and again, feel mutual excitement. And then, you know, the other lesson there is just teamwork. Just give a damn about the people around you. We're essentially all grown-up children with a whole lot of stuff on our shoulders. Some of us have kids, some of us have mortgages. We're trying to do a good job and be a good person. So it's rare that people are, I guess, intentionally malicious. So giving people the benefit of the doubt is always kind of best practice.

5:11 Scott Ingram: All right. My favorite part of all that, even though there is a ton of greatness, is grown-up children. Like, that landed.

5:16 Jack English: Oh, it's true though.

5:18 Scott Ingram: I feel that.

5:18 Jack English: Exactly.

5:21 Scott Ingram: Oh, so let's talk about 80/20, right? Like, so when you think about that 20%, what have you found that to be for yourself?

5:28 Jack English: Interesting. All right. I like the specificity of that question. I guess from a macro perspective, it's, I guess, to set the table on 80/20, you know, we want to focus on the 20% of deals that are going to make the biggest impact on us hitting our number. It's going to be the 20% of things within a sales process that actually make the most difference to us moving this deal forward. It's the 20% of things that matter most to your own boss when you're managing up, right? When you're kind of saying, okay, what's my boss's plate? What's he got to report up? How can I help him look good to his boss? And it's really a cheat code to life. So what I've found for me that's most important is kind of honing in on my unique selling points. So for me, I'm really good at top of funnel. That's, you know, I can manage the whole cycle. Obviously, I'm an account executive. But for me, I found that what differentiates me from a lot of my peers is being extremely voracious in terms of the top of funnel that I'm able to collect. And it's not about, for me, you know, smoothing out every part of my ability as a salesperson to make all of myself mediocre. It's about really focusing on that small piece of me that makes me already exceptional and then doubling down on that to kind of 10x the results, so to say. I'm sorry that I sounded like Grant Cardone there. That wasn't my intention. But for me, I've found that if I'm able to differentiate or excuse me, distinguish really clearly why I'm different, then a small investment in energy and further improving that skill results in a really big improvement at the end. And I've seen or found that, let's say, more mediocre reps have a hard time distinguishing that 80/20 and as a result spend just as much or even sometimes more time on those activities that yield very, very little in the long term. You know, chasing a deal for months and months that you could essentially disqualify today based on I don't know, a single call and 3 questions to the prospect.

7:08 Scott Ingram: Love it. Love it. I think it's also interesting that you're putting basically the internal management, managing up into that mix. You talk about, you know, really doubling down on your strengths. What are your strengths? Like, what are those things?

7:20 Jack English: Okay. I think there's really 2 things that have helped me get to where I am today. So I think going back to the previous answer, I think I'm really, really good at generating a lot of top of funnel. And that sounds really kind of obvious and whatever. But I found that making or creating a lot of top of funnel excuses a lot of mistakes further down the funnel. And we can certainly talk middle of funnel and bottom of the funnel later on the call. But I think being able to consistently generate pipeline takes a lot of the lack of control that a lot of sellers have away. A lot of sellers say, hey, I don't have enough leads. Hey, my BDR, you know, went to sleep all day and didn't book many meetings this week. Now I'm screwed for the quarter. I think if you can take that or take that ownership upon yourself to generate a lot of that top of funnel pipeline, you can essentially put yourself in a position where you're relying a lot less on external factors. So I think that's really important. And then the other one is being, how should I say, being pessimistic in the right ways. I think always asking yourself whether you've just come off a call or whether you're, you know, in a strategic review with your manager about a deal that you've been working on for 3 months, 6 months, I think being incredibly pessimistic ultimately positive about your life. Let's not be nihilistic, but pessimistic about the deal and all of those red flags that might be there lurking under the surface is a real unique benefit that I have that other folks have shared with me. And it's really important because that's how you dig out the things that you might need to focus on a little bit more specifically. And in government, which is where I sell, I sell into GovTech, there are some really interesting lessons I've learned that have caused me to be a little bit more pessimistic over time. And maybe some interesting stories there that we can dig into.

8:53 Scott Ingram: Right. Like those processes aren't gonna move fast, right?

8:55 Jack English: That's correct.

8:56 Scott Ingram: So, well, let's contextualize, and, and I'm looking forward to coming back to a lot of this. Yeah. Especially the top of funnel stuff, right? Which I think ties in so well to your 3rd point, which is about ownership, right? If you take personal responsibility for your pipeline, even if you do have an SDR, BDR supporting you, then to your point, like you get to be a little bit pickier.

9:14 Jack English: 100%. Absolutely.

9:16 Scott Ingram: All right. So tell us a little bit about your role and how you got to the top AE position.

9:22 Jack English: Alrighty. So my role, I'm at a company called Zencity. It's a pretty interesting name. I'm the sole enterprise AE. And what that basically means is that I manage our relationships with cities and counties over 500,000 in population. So that could range from, let's say, a relatively small county like Jackson County, Missouri, all the way up to the city of New York and the city of London. I began at Zencity, let's say 18 months ago, almost 2 years ago actually, selling to really small cities on the West Coast. You know, we're talking like the city of Atwater, you know, a few thousand residents. And when I actually first started out working this role, I was still living in New Zealand, which was really interesting because if you have any idea where that is, you can figure out pretty quick that the hours aren't quite congruent. So add to that mix a sales manager in Israel, and it was interesting. I was waking up at 4 AM to take East Coast calls, working through to mid-afternoon, but basically just grinded there. My first year there hit over 180% of plan on a ramped quota. And from there, the company wanted to focus specifically on the enterprise space based on some, you know, evidence that we'd seen of that really catapulting our business. I was chosen as the rep due to my success in SMB to begin that team from the ground up. And the other thing is, the reality is I was really burning out in SMB. I'd had another job offer on the table for a lot more money, a big increase in OTE. And really genuinely considered them. And when it came down to it, trusted my intuition that the opportunity on the table in front of me continuing with Zencity, I could see, and, you know, based on my subconscious, let's say, analysis of the situation, the product we were selling, the market we were selling into, my teammates, I saw a big opportunity there. So I decided to stay with it. From here, it's really been an experience of, I guess, rolling with the punches. And that always, you know, comes with being at a relatively small company, only a couple hundred employees. My results for the previous year ended up selling $1.8 million ARR against a $1.1 million quota to make over 160% of plan. And as of Q2 this year, quota will be moving up to around $3 million.

11:16 Scott Ingram: Brilliant. Brilliant. So let's talk about kind of the origin story and how did you get into sales in the first place? And obviously we certainly want to spend some time on, you know, how did you move so quickly through your career to a place that you're, you're at the top of the leaderboard and making great money?

11:32 Jack English: Let's do it. Alrighty. So a lot of people, I obviously listen to your podcast religiously and a lot of people come on here with the story that, you know, they actually began selling as kids. They were like marching around the neighborhood, hawking lemonade and whatever else, mowing lawns. Mine, definitely not even close to that. Mine actually came out of necessity. So originally I'm from New Zealand. That's why I sound a bit funny. And I ended up in the US for college, did my 4 years in the US. And for listeners that may not be aware, as let's say a foreign student, after you graduate, you're allowed 1 year to be in the US to work. And then after that 1-year period, You either have to get a company to sponsor you for an H-1B visa or you're gone. So you're in this process where you graduate and the clock's ticking on your 1 year. And basically, I studied economics. I couldn't get a job in economics. I had an undergrad degree from a liberal arts college. It wasn't going to happen. No one was going to employ me for a single year and then having to sponsor me at the end of that. No chance. My friend said, hey, have you ever thought of being in sales? You're kind of weird, but you like talking to people, so maybe it might be a fit for you. And I did a little bit of research and you said, hey, what have I got to lose? So really it came out of necessity being into sales. And without realizing, I kind of began selling before I even had a job. I created this Excel spreadsheet. It had like hundreds of rows and then kind of created a bit of a pipeline, right? So on the left-hand side of this sheet would be all of the companies I've reached out to. So I was researching, you know, hundreds of companies on LinkedIn, firing the hiring managers, finding the VP of sales and reaching out to them. And then in the middle column, I'd have a shorter list of companies that had, let's say, replied positively to me. And then on the right column, a list of companies that we had extended conversations with. And in that way was basically creating a sales funnel, obviously selling myself rather than a product. And eventually got a job with a GovTech company in Boston. Never been to Boston, had no idea what GovTech was. Tiny company. We were like, I don't know, 18 people putting together everything with bubble gum and toothpicks, but landed there and said, hey, this is what it is. I'm going to make it work. Basically what ended up happening was did really well. Hit my number and about 6 months in, a bunch of really well-to-do or really buttoned up men, let's say, in nice shiny suits walked into our office and said, hey, we've just bought your company. You're now part of a big company. So that was a little bit of an interesting experience. We were acquired by a Silicon Valley company. My whole growth trajectory, which was, hey, I was about to be an AE at the small company, got thrown out the window and I went back to square one as an SDR. I went in, you know, I marched into the VP of Sales office at this really big company. I said, hey, you know, My previous boss said I was going to be an AE. Am I going to be an AE tomorrow? And he kind of laughed me out of the room and said, get back to work, kid. So from there, it was kind of down to putting my head down and saying, all right, I've proved I could do this in a small company, but can I still do it at a larger company? Can I, you know, compete with the big boys and girls? And was able to do that, created really strong relationships, found some mentors, Eric, who I mentioned earlier, and just kept blowing the number out of the water. So in my 18 months there, averaged 214% of plan as an SDR. From there, you know, the story continues.

14:19 Scott Ingram: Awesome. Awesome. Awesome. Well, and it sounds like that maybe additional time that you hadn't planned on in being an SDR, it sounds like that's really served you well in your ability to continue to generate pipe. I mean, was that kind of a blessing in disguise?

14:32 Jack English: You are so right. It's amazing how few people realize this. You know, as we're young, we're like, I hate this job. I hate cold calling people. I want to be an AE. I want to be controlling my calendar. I want to be, you know, the big one doing the negotiations. Cutting the contracts. But you're absolutely right, Scott. Every day I thank myself until the sun goes down that I was made to be an SDR for, you know, going on 2 years because it taught me so many vital lessons, not only in terms of, you know, hustle and grind and all of that important stuff around having a great work ethic, because no one has a harder work ethic than an SDR, in my opinion, but also giving you time out of the spotlight to, let's say, marinate and understand what actually makes a sale rather than, you know, being promoted after 6 months, getting thrown into the lion's den, in front of prospects and saying, hey, you know, sell this product, which I saw fail over and over again and consistently to this day see fail over and over again. Going, being as an SDR and finding someone that's going to mentor you and bring you in on calls, bring you in on first calls, give you a little bit of talk time with the customer, get you, you know, comfortable with it. And then not only on that first call, but then bring you throughout the cycle of the deal. My AEs at that previous company, you know, I wouldn't just stop at the first call. I would be, you know, on Salesforce like a hawk looking for updates to the deal. I'd be messaging them on Slack, understanding, hey, why did you ask that question? Why did you not ask that question? Are you gonna follow up with him today or are you thinking of following up with him next week? Why did you make that decision? And I think you're absolutely right again, that taking the time to be a little bit more thoughtful compounded massively in the speed. It's kind of one of those things, you know, it's the boring quote about Abe Lincoln sharpening the axe to cut down the tree. Absolutely was a huge benefit.

16:04 Scott Ingram: Yeah. You know, this thematically has come up quite a bit in this conversation because it's, I mean, it's one thing to be successful as an SDR. It's a different thing to also continue that trajectory and be successful as an AE. I'll call out a link for listeners. I'm actually, it's been a while since I've had a top-performing SDR on here. So we kind of get to check this box with this conversation. But if folks go to top1.fm/sdr, you can go back and listen to a lot of the SDR conversations. And I actually think the sweet spot is probably 18 months to 2 years in that SDR role to really set yourself up to be a great AE. Yeah. I mean, you can all, you kind of break it down into 6-month chunks, right? And tell me if this resonates. Like the first 6 months is you're just figuring out your life. Like you got to figure out this role. You got to figure out the company. This might be your first job, right? Or it's the first time in this industry. Like it's going to take a minute to get your head around this. The next 6 months, like you can really like find your stride, right? And start to get good. And then at about a year, like you should be good. Right? I mean, if you're really applying yourself, like you should be solid and then you essentially should be performing well, which is going to set you up for the opportunity to move into the AE role, right? You want to make sure that you're well ahead of your numbers, but you should also have some extra cycles to do exactly what you described. And now you want to dig in and shadow the rest of the sales process because you're never going to get another opportunity to learn that. And it's a lot easier to learn it from the outside rather than like standing in the fire.

17:35 Jack English: 100%. I think that's really important. And, you know, we see it, I see it day on day, even within SDRs that I work with, they're constantly asking, you know, how do I become an AE? Why is my boss, you know, I've been here 4 months, am I ready to be an AE yet? They promised me this, they promised me that. Is it time yet? Is it time yet? And it's one of those things where when you're in it, you don't have that perspective, unfortunately, to go, hey, in the long run, this is actually going to be to my benefit. It's very much, how should I say, moving up as quickly as possible. And as salespeople, we naturally have that inclination. But I think it again goes back to that mentorship point around having those people in your life that say, hey, young one, slow down a little bit, take your time because you're learning a lot, even if right now it doesn't seem like you're moving as fast as you'd like to.

18:14 Scott Ingram: Yeah. I mean, at the end of the day, I think it ends up being a force multiplier, right? That extra 6 to 12 months is the difference between being a mediocre or even underperforming AE, and maybe you don't even have the opportunity to continue in sales or being a great AE and making 2 or 3 times the mediocre AE's income?

18:34 Jack English: Yeah. I mean, unfortunately in this market, you know, every company's seen, I assume, a lot of AEs come and go. And for me, the core reason that I see consistently is a lot of reps just don't have enough pipeline. You know, you can improve your sales skills by 20%, by 30% at bottom of the funnel, but at the end of the day, improving your efficacy at sourcing pipeline at the top is massively going to increase your input. So it doesn't matter if you're getting really good at the bottom, if you're still only working 2 or 3 deals a quarter and you have to hit every one of those to make your number, the numbers just don't match. So I think a lot of reps unfortunately either don't go through that trial by fire of being an SDR, or once they get out of it, kind of wipe their brow, go, phew, never again, and kind of relegate prospecting or top of the funnel sourcing to somebody else, unfortunately.

19:17 Scott Ingram: Great stuff. So, you know, I call the show Sales Success Stories. Do you have a story of a particular sale that is meaningful for you? Maybe it was a big win, maybe it was a big lost that you learned a lot from. What's that story?

19:31 Jack English: I definitely have a great story here, at least for me. So we again work with cities and counties, and I was doing a little bit of a road show, as we like to do when we're dealing with governments, because obviously geography is everything. So I was driving through, I think, the Southeast, and I'd emailed a bunch of prospects saying, hey, I'm going to be in your town, I'm going to be in your city. Booked a meeting with a massive county, the largest county in its state, and was like super excited, right? So I was going to go meet them in person And it was actually the chief of staff. So essentially the second in command of the county. Again, fantastic. The meeting was planned. You know, I was in my Hyundai Sonata, I think it was a rental, driving down to the city and, you know, the day before it gets canceled, pushed back. I go, oh, fantastic.

20:09 Scott Ingram: All right.

20:09 Jack English: So it's pushed a month. I'm obviously not going to be in town. Let's turn it to Zoom. Fine. So, you know, it was booked in October. Now we're talking about doing it in November and the week comes up for the meeting, pushed again. Now we're meeting in December. And if you've been in sales for longer than 2 minutes, this is like, this is disaster zone. We're going into that first meeting going, there's zero chance this person's going to have any interest at all just based on that kind of pre-meeting behavior. But, you know, whatever it was, jumped on the meeting and it was nice. You know, it was a pretty solid first meeting. It was very quick, just a little bit of a disco call. And they said, you know what, this is worth chatting about a little bit further, but it's Christmas coming up. We're in December now. Let's talk in January. I mean, all right, we're now, we're talking, you know, 5, 6 months since it was first booked, but let's do it. Second meeting, this was now the demo in January. And the thing about it was at this point in our company's, let's say, transition period, we were moving from a point solution to a platform approach, but no one had ever sold the platform before. It was kind of like, hey, we think we can do it, but we're not actually sure if it works. And on this meeting, because it was such a large county, we were like, you know what, let's show the whole kit and caboodle. So it was just me and my sales manager. And this individual, we actually went against the book a little bit in a couple of ways in this deal. And the first way was we showed software for the sake of showing software. You never want to do that, right? You always want to match specifically what you're showing to exactly the pain points that you found in discovery and nothing more, nothing less. But on this call, we weren't really hitting the mark, right? They were going, yeah, that's kind of interesting. And we said, you know what, we're not going to get another shot at this. Let's at least show them this new feature that we've got. We showed it and they went, oh my goodness, this is exactly what we need. We've got this initiative that's rolling down from our elected officials and local government elected officials are everything. And this looks like it will fit the bill exactly. Let's get on another call next week. We get on another call, we get on another call, and now the ball is rolling super quickly. We give them a quote. It was by an order of magnitude the largest quote that I'd ever given to a customer at Zencity. And they said they didn't even blink twice and actually made me think I probably should have quoted a lot higher, but that's a conversation for another day. And then we went, you know, one further. We actually met the chief executive of the county, which is basically like the mayor. They loved it. We're, you know, kumbaya, this is fantastic. We're going to blow our quota out of the water. We got super creative with procurement. We're doing a phase 1, phase 2 approach to get, you know, to help navigate some of their more antiquated procurement that we see in local government. And all going well. I remember the day specifically, Scott. It was a beautiful 10 AM morning here in Mexico City. The sun was shining. I was walking back from a beautiful, I think it was a ham and cheese omelet from a cafe. And I opened my phone, I scrolled down the preview pane and I get an email subject line, agreement not moving forward. Okay. I have a mini heart attack. I read the email based on some bureaucratic nonsense. The deal's no longer moving forward. All of the work we've been doing, all of this hope and expectation that we put into this deal was just out the drain. So I kind of try and collect my thoughts and, you know, I'm drafting this email to send back. And as I'm drafting this email, I get another email back from the prospect. Ignore the previous email. I just went and spoke with somebody else. We're totally fine here. We're going to keep going. And so this is the first heart attack I had from this deal, but they'd keep coming. The reason they keep coming is that in local government, going back to those elected officials, so not only do they tell, let's say in this case, the county staff, hey, do this, do that. But then once they tell them, hey, do this, do that, when the staff come back to them with a solution, in this case, a software solution, well, the elected officials now have to vote on that. And that's really fun because if anyone knows anything about politics or a local government, that's not always going to be exactly a straightforward process. So what do elected officials like to do? They like to get reelected, which means making political stands on certain issues, right? Purchasing decisions are an easy one to make a stand on. Some electeds, you know, don't even want more data. We're a data collection tool for local governments because it makes it harder to justify their otherwise maybe more self-interested policies. Some will make a stand because they had an argument 2 years ago with some staff member who's now behind the product. You know, the point being that it's very, you're down to the line, right? It's 7:30 on a Tuesday night and we're counting the votes. Yes, no, yes, no, so on and so forth. We're sitting on the Zoom and eventually pass. I think it was a 5 to 3 vote to finally get this deal moving forward. And obviously we were extremely, extremely excited. Which is great. The deal passed. Then we, you know, get the agreement signed. The final thing, the other piece of the puzzle, the big no-no that we did, the second no-no on this deal, the first one was showing software for the sake of it. The second no-no was actually now we had to turn around and tell our technical team to essentially build something that didn't exist at that point in time. And obviously you never want to do that because you're out over your skis a little bit. But credit to not only our CEO, but our technical team put everything on hold and worked around the clock to get the solution built. Which was such a success that, you know, during the initial presentation, a month and a half after signing the contract where we said, hey, this is what we built for you, to the prospect, they said, hey, I looked at the market for like a year before talking to you guys. This is the best thing I've seen. So all in all, a lot of ups and downs, but that's what makes sales such an exciting industry. And ultimately we won, which is the most important thing.

25:04 Scott Ingram: That's awesome. So after the first heart attack moment, did you call them to figure out like, why did you say the deal's off and then it was suddenly back on? Did you figure out what was behind that?

25:14 Jack English: So almost, they explained it came down to a deputy director of a specific department coming up against a specific way we were running the procurement process in a phased approach. They got cold feet. They went, they tried to pull the plug. And essentially before I even had the chance to pick up the phone or email back, literally within, I think it was like 12 minutes, we got the email again saying, wait, no, spoke to someone else. We're all good now.

25:35 Scott Ingram: Oh, I think we've all been there though, right? Like that whole, just the visceral, like I've got this great deal where You know, 9/10 of the way there, we're on the 1-yard line, whatever analogy we're gonna use. And then you get the email that just completely rugs the whole thing and you go into panic mode to figure out, okay, how do we save this thing?

25:53 Jack English: You know, the worst part of it, Scott, is that like the best part of the deal is way, way, way before you even get the signed contract, right? It's like the first time you present the quote and they say, I wanna move forward, you've peaked. Like that's the best you're gonna feel about that deal. And from there it's only moving down. Essentially, yeah, when someone tells you we're not even moving forward, it makes all of it even that much worse.

26:11 Scott Ingram: Well, you know, and that the irony in that is when you're running a good sales process, it's almost like the signature, the actual technical closing of the deal is just another step in the process. It really is anticlimactic. You're exactly right. Like the emotional peaks happen at different points and they happen at the 2 or 3 times when you do do the diving save. Because there is something in the way that tries to blow up the deal and then you figure out how to save from that. And those are fun.

26:38 Jack English: Yeah, exactly.

26:39 Scott Ingram: So you've accomplished quite a bit in a relatively short period of time. What are you most proud of?

26:45 Jack English: What am I most proud of? So, okay, I'll tell a little bit of a down story and I tell it as a little bit of a redemption, but in 2020, COVID hit. I was actually in Canada. I was stuck in Canada and because of the borders were shut, right? I kind of flew in and then they shut the next day and that was where I was. To get… to be super honest, I had a horrible time. I actually had a little bit of a mental breakdown and had to fly all the way across the world back to New Zealand to go live with my parents again. And, you know, I'd been successful in my role. I'd moved across the world. I'd done all this amazing stuff. And here I was, you know, sitting in my parents' bedroom, basically unable to see a path forward based on, you know, what I'd seen, what I'd been doing so far. And that was the lowest I'd been. Took a lot of therapy, really had to understand what was going on with myself. In that point, I also took a new job. I couldn't continue working that current job from the geography that I was now in, which was New Zealand. So I took a new job, had high hopes, you know, I was going to crush it, it was going to be fantastic. I failed. I sucked. I sold nothing. And, you know, there's a few reasons that we can get into there that serve as good lessons when you're looking out for sales jobs. But the point being was that like not only was I mentally broken, I was failing professionally, which, you know, for a lot of us is how we kind of measure ourselves. And it took, you know, 7, 8 months really to go through that process. And eventually, it came down to being super honest with myself, but most importantly, stepping again outside my comfort zone and getting rid of that job, taking a remote job from New Zealand, working with an Israeli company selling to the US again, doing something that had zero chance or close to zero chance of success based on what I could see. And what I'm most proud of is being able to get through those really tough periods with a positive perspective, And one in the sense, or one that has given me now the perspective to see, hey, those really important or those really difficult places that I've been were the most important. We all know success is a really lousy teacher. You come off a great quarter, that teaches you nothing. You come off a really terrible quarter, you lose a really terrible deal, that's when you learn the most. And I think for me, being most proud of going through those really tough times and coming out the other side has given me an understanding of my own capacity way, way more than the really good quarters ever taught me. When I'm, you know, when I have a good quarter, yeah, you're great, you're amazing, you're fine. But when it's going through a tough period, coming out the other side, and then looking back at yourself, that's when you begin to have a level of respect that, you know, money cannot buy.

29:00 Scott Ingram: Love it. Love it. Let's get into some of those lessons learned. And it would… it seems like you alluded to was part of it was just kind of wrong fit. Is that accurate?

29:08 Jack English: Yeah, totally. So I'm a sales gentleman at my heart, as you know, a lot of us are. And basically what ended up happening was there was this really successful product that was being sold in the US, you know, $50 million ARR, over 1,000 customers. Product market fit was right there. They had 2 customers in Australia and they were using a reseller. This reseller was like an 8-person mom-and-pop consultancy company that said, hey, we'll take your amazing flashy software, we'll use our relationships here in Australia and we'll, you know, ramp it up and sell it and you'll be… it'll be selling like hotcakes. And I was kind of coming into that little small 8-person company to be that salesperson because I had a little bit of experience with that software from the US. And it was a disaster. There's really no other way to say it. That company had never sold a piece of software in their life. None of the infrastructure was there, unfortunately, to support a sales funnel or a sales pipeline. There was nothing like Salesforce or really any sales enablement tools. And we're out here immediately with a quota of over a quarter million dollars on your back. It's very difficult. So I think going back, it was important to understand, yes, from the outside looking in, what makes a good company and what makes a bad company from a fit perspective. But that can be kind of obvious, right? Like if you're selling, if you're, let's say you're a young person now looking at jobs and there's like a seed round company selling HVAC automation out of rural Pennsylvania and they've got 0 clients or 3 clients, you can probably tell from the outside looking in that might not be a rocket ship. So that wasn't the most important piece for me. It was way more important to look internally at different companies and how they operate and how the culture is a fit. That really, I think that's only a lesson you can learn when you've been in a bad culture where someone does, when you're on a sales call, really yell at you in front of a client and tell you to shut up because you don't know what you're talking about. And that did happen at that smaller company, right? And when you're in that period, you're going, is this normal? Like, do I just shut up and accept this? And it's only through going through those processes and coming out the other side and understanding, wait, no, that's actually not normal. That provides kind of those scars that once you look forward into the future, you can actually begin to find those right opportunities for you.

31:07 Scott Ingram: Yeah, good call out. I mean, that is such a huge theme for us this year, just this idea of sales culture. And it ties into some work I've done the last couple of years just around, you know, how do you do the due diligence around a job to make sure that it is going to be a good fit, that you are set up for success, and that you're not going to have one of those career wrong turns. But the reality is, I mean, as proactive as you try and be and as hard as you might try and work at that, like sometimes you just have to go through it yourself. Like sometimes, like that's a thing that a mentor can't work with you on. Like you might have to live the experience that is, oh, but I'm gonna make so much more money and realize that, yeah, that like we've probably all had one of Like the opportunity just seems so great and on paper it's amazing and it's all about the money and there are some things in life that are just not worth it.

32:04 Jack English: Are there any, I guess, question of curiosity, are there any low-hanging fruit, let's say questions or pieces of information that you think you can dig out, Scott, when you're, let's say, engaging with a prospective company to work for that might tease out some of those red flags?

32:16 Scott Ingram: Yeah, totally. So I did a whole, what's really funny is I threatened for a really long time to put together a resource around this and in my head I had I was thinking I needed to put together some type of guide or something in writing, and it took me way too long to remember, oh wait, I'm a podcaster and most of my people listen to what I have to say in audio. So I did an episode not too long ago around kind of this due diligence idea. So in the show notes, so top1.fm/this episode number or top1.fm/jack-english, I'll link to that particular resource. So I mean, we talk about a ton. A ton of stuff in that. The thing that I find to be the most helpful is you just have to have as many conversations as you can in and around that organization. And I think one of the best hacks is find people who have been there recently but aren't there anymore, because then they're not really tied to the outcome. Like, nothing's going to come back to them. And I think this is also important Because, and just some very, very recent stories around just how impactful your direct manager is on your success. I mean, you talked about a positive example.

33:27 Jack English: 100%.

33:28 Scott Ingram: And I was just having a conversation with a great friend who is in a great sales culture working for a not great manager. And like, she's ready to quit over it. That's how impactful it is. And I've said for years, And maybe there's examples, but I don't think I have talked to anybody on this podcast who is successful despite their manager. Like, sales is way too hard. There's so many challenges to overcome. If you also have to overcome a bad direct manager, it's one thing too… it's too far. So, the other thing that I will do is I try and do some backchanneling on that manager. I find people that have worked for them at a previous company or a previous company. And it's one question. It's, if you had the opportunity, would you work for this person again? Like their answer to that tells you everything you need to know.

34:21 Jack English: Okay. Not to turn the podcast around, but I have kind of a follow-up question. I suspect a lot of your listeners may be in the position where they don't hate their manager, but they don't know if they have a great manager. Are there any, let's say, ways, or what are some of the hallmarks maybe of really good management and leadership?

34:38 Scott Ingram: Yeah, that, you know, that's a great question. I'm going to tie that back to your, your third point around ownership. Right? Like it's a two-way street. Like the relationship with your manager is not just them. Like you don't just wait. It's not like your pipeline. Like you can't just wait and hope that it's going to be great. You have to contribute to that relationship. You know, if you can figure out what's important to them and what drives them, what their style is and how you kind of match those styles, right? And some of it is just getting really deep in with them. And if you know yourself well, being able to articulate what you need from them, right? I mean, because sometimes it's, I need help navigating our organization in some way. Like, I don't have enough of a relationship with the product team or with the legal team or whatever it is, like, to work through this issue. Can you help me with that? Or maybe there's a skill area that you're trying to work on that they can help coach you on, or they can kind of watch you for, right? So the more that you kind of think about that relationship and leverage them and say, hey, You know, Jack, I'm really trying to work on this. Is that something you can help me with? Right. And again, like taking ownership of the relationship.

35:45 Jack English: Yeah. And I totally 100% agree. I think the other thing that is a glaring difference between like an okay manager and a great manager is you feel like they really 100% care about you and your success and your life and your wellbeing. Because I think once you've had a manager that you feel, wow, this person is actually invested in me. Way beyond my number, but actually how I'm doing. And it sounds kind of like a Hallmark Christmas card, right? Like, you know, I want someone that cares for me and all of that. And should we expect that from our corporate side of our life? Well, once you have it, I would never go back to a manager that doesn't provide that for me. I think that manifests in really good ways or in really interesting ways. The way I tell if a friend's a good friend or a great friend is if they're willing to put their backside on the line and tell me things about myself that I might not want to hear. If I'm engaging in bad behavior, if I have a bad habit, and is my friend going to go, hey, you know what, Jack's going to do Jack because he's Jack? Or is that person going to actually have a brutal and honest conversation with me and say, hey man, I've noticed you're doing X, Y, and Z. You already told me in the past you didn't want to do that. I'm just letting you know I'm noticing you do that. And making me confront parts about myself that I'm not 100% happy with, that's the sign of a great friend, of a great manager.

36:52 Scott Ingram: Yeah, I think you nailed it, right? I think you really can boil it down Do they care more about me than their own number? Right? Because if they do, I mean, that's kind of the perverse secret to leadership is if you do do that, if you do care more about your team, you're going to hit your number because they're going to work for you. Like they're going to go above and beyond and try to help you. Right? And I think you can apply that same thing to a great salesperson. You know, a great salesperson cares more about the customer, their outcome than they do their quota. And when you do care about that, the quota takes care of itself. Yeah.

37:28 Jack English: The unfortunate thing is that a lot of us are kind of like hungry rats backed into a corner, starving because, you know, we're terrified every quarter it starts again at zero and we're not going to hit our number. And it puts us in this kind of weird traumatized mentality where we're coming from a place of scarcity as opposed to a place of abundance. And that manifests in our conversations with our colleagues when we're a little bit snarky, when we're very transactional, when we just need something from them and ask and don't take the time to understand how that's going to impact them all the way through to your point, to conversations with clients. And rather than actually taking a little bit, you know, a little bit more time, having an extra call to understand what are the impacts for this person individually, going immediately through your, let's say, prescribed sales process because I want to get to the finish line immediately because I need this deal because I have a quota and I need, you know, to put food on the table.

38:10 Scott Ingram: Yeah, I think we actually touched on it earlier, but it's worth coming back to. I mean, didn't you say that that was kind of the first lesson that you had to learn, that you had a great mentor around that was, man, you sound desperate. You care too much about yourself and your number. You don't care at all about the person who you're trying to sell to.

38:28 Jack English: You're exactly right. Exactly right. And that's why mentoring is so important, right? It can tag you onto some of those really important behaviors. And in a way, podcasts like this are mentorship. They're not such a direct relationship, but I think this is totally in the same vein of, I'm sure this is a question we're going to come on to based on some of your previous podcasts, information diet, but piping into your brain some of the substantive content on an ongoing basis is… can be just as important as having some of those in-person mentors as well.

38:51 Scott Ingram: Yeah, absolutely. And I've said forever, like, this podcast is basically mentoring at scale, right? You get to talk to me for an hour and a half or whatever it's going to be, and now thousands of people will have an opportunity to be impacted. And you could never have 1,000 one-on-one conversations, right? So it's such a…

39:07 Jack English: exactly.

39:07 Scott Ingram: I love this medium so much. Let's keep going and let's get into kind of some of that habit routine information diet type of stuff. And you listen to the show, so you know that probably my favorite question to ask is your alarm clock goes off… oh wait, you know what, before we go there though, I think it would be just mostly out of my curiosity, but that just reminded me when you were talking about it being challenging to work with the West Coast out of New Zealand and the time zones being complicated. Heck, the days are complicated. Like, literally the day is different. Just, I would love to have just a little bit of context on like your geographical history, right? Because we've talked about New Zealand and the Northeast and Mexico City and Canada. And so, what's going on there?

39:49 Jack English: I'm a little bit of a wanderer. When I was 18, I left high school, I put a pack on my back and ended up in Bishkek, Kyrgyzstan. And it took a whole year going through Central Asia and Eastern Europe. And that was amazing. And from there, went to the Northeast. From there, went to Canada, had the big mental breakdown as we… as I proudly spoke through and then went back to New Zealand. And you're totally right. Not only are the days way off, but then we add in the fact that I work for an Israeli company. FYI, Israel works Sunday to Thursday. So if you're looking at the calendar from New Zealand to Israel to the US, I think there's like 3 hours during the week that we're actually all working at the same time. So 100%, it's a little bit strange. Now I am in Mexico, it's a little bit nicer. So I have a little bit more of a, let's say, normal work schedule. My customers are in all 3 time zones of the US. And it's pretty simple when I wake up around 7:00 AM. I'm not kind of one of the 4:00 AM wake-up people, but maybe one day I'll get there. I'm waking up, I'm immediately looking for a reason to smile. It sounds kind of cheesy, but if I look out, I don't know, the window and the sun's shining, I'm good. If I get a message from a good friend that lives in a different time zone over the night, I'm good. It's really important to, let's say, get the jump on the day mentally and have the first few thoughts in your mind be good ones. And for me, News or Slack or Instagram Reels are usually not that. So after that, I'm kind of getting up out of bed by 7:30. I'm logging on, tackling some low-hanging fruit. Given HQ is in Israel, as I mentioned, you know, this is usually a few Slack messages, maybe regarding a client or an open opportunity. Once I wrap that up, coffee and exercise time. I'm pretty religious around exercising. For me, it's a massive mental health boost. I love it. From getting back around 9:30 in the morning, that's when my day officially starts. So some would call it a little bit of a late start and, you know, you'd probably be right, but it's where things have ended up settling for me. Throughout the day, I work remotely, so it can be a little bit isolated from a social perspective. On an average day, just based on the working on the enterprise side of the business, I have around 1 to 2 client meetings. Generally try and put those around midday. That's when I feel most in the groove. They're not getting me right early in the morning as I'm a little bit groggy and I'm It's not early afternoon or, excuse me, late afternoon where my energy is on the wane. Late afternoon is really where I'm doing a lot of, let's say, outreach, cranking out sequences, scheduling, doing some more administrative work. And then pretty simply, by 6 o'clock, I'm usually out the door. I love to climb. I'm taking Spanish lessons. Scott was grilling me before the podcast on my Spanish. Didn't hold up. I'm known to get my butt kicked at Muay Thai a few times a week as well. So, something, getting out there into the community and then really back home by let's say 8:30 or 9, eat dinner. If there's a proposal to put together or a slideshow to present for the day tomorrow, I'll do a little bit of that work late at night and then straight to bed. On a weekly sense, my manager, my current manager, Bara, instilled in me to be pretty regimented on only scheduling external meetings between Tuesday, Wednesday, and Thursday. Oftentimes, especially in government, Monday's firefighting. From whatever was happening over the weekend. Cities don't stop running over the weekend, but the emails are attended to on a Monday. And then Friday, a lot of people, they're off, let's say hypothetically, on vacation. On the rare occasion, sometimes you can have a good Friday meeting due to, let's say, I don't know, the weekend tinted glasses, but often just as much momentum can get blown by the weekend, people forgetting things, and all of a sudden Monday runs around and you're the last thing on their plate.

43:06 Scott Ingram: Too funny. All right. I have… you made me laugh about my grilling you on your Spanish. That was, I'm going to say, misrepresented.

43:12 Jack English: Don't do it again, please.

43:15 Scott Ingram: So I also want to clarify, you like getting your butt kicked in Muay Thai. That is a martial art, not a drink, correct?

43:23 Jack English: The drinks come after. You're exactly correct.

43:25 Scott Ingram: So, and then how did you end up in Mexico City? Because there's no linearity to that. How does that happen?

43:31 Jack English: Yeah. So basically, I do work. So taking the listeners back to the beginning of the call, I'm not a US citizen. I need an H-1B visa to work long-term in the US. I've had multiple companies apply for those from me. The success rate is very low. You're talking around 10 to 15% of actually getting through. So I can't live in the US as it stands today, but I'm working US hours. So I really have a couple of options. I want to be close to the US for travel and for convenience. I can choose Canada. Well, I lived in Canada and that ended up in me having a mental breakdown, as I mentioned. So I didn't want to tempt fate there again. So I said, you know what, Let's give Mexico a try. Came down here for a month and really enjoyed it. The weather's fantastic. The people are some of the kindest and most welcoming on the planet. Everything in between. The nature here is fantastic. Have a great group of friends and ended up coming for a month and have now been here coming up on a couple of years. So that's where I'm at full-time.

44:22 Scott Ingram: That is fascinating. And I have to imagine the cost of living is pretty awesome too.

44:26 Jack English: Depends where you are in Mexico City. As a lot of people will know, prices are not as cheap as maybe they were 5, 10 years ago. There's… I'm not the only person that's moved here. So, depending on where you live, there might be a delta on some things of, let's say, 20% to 30%. And other things that might be imported are a little bit more… can be even more expensive, as I found out when I bought a phone recently. So, it really comes down to specific things. Uber, cheap. Real estate, getting expensive. And other things in between.

44:50 Scott Ingram: Fascinating. Fascinating. All right, cool. So, let's keep going on. So, we've talked through kind of the way that you are structuring your day. Are there any other habits or routines other than starting smile that are kind of core to your success and your approach?

45:03 Jack English: I'm pretty, let's say, religious about syncing with the wider team every day. So we… I'm part of a… I'm the enterprise AE, so kind of quarterbacking it. But obviously I work with a team of fantastic people. Some of those have an ex-sales background like me, some of them are in management, some of them are actually ex-local government. We have some pretty amazing resumes on our team from past local government experience, and I do make it a point every day to connect with the folks on my team around specific deals. A, because, you know, massively helps efficiency rather than just writing on Slack and writing emails, just to get on a call around, knock out everything around that, you know, 6 opportunities that we might be working on first thing in the morning. Everyone goes away knowing exactly what they have to do and focus on to moving the ball forward a couple of yards that day. And then B, it just goes a long way to creating a good sales culture. And I'm so, so, so thankful, just as having a good manager is important, having a that great team is important. I now get to say I work with people that like I genuinely, genuinely enjoy talking to just as much as my friends. And that's another thing when unfortunately you really don't have the ability when you're looking into a company from the outside to judge that. But it's just that, you know, when let's say lightning strikes and you're in that position, you really have to be thankful for it. And that's something that I'm super intentional about is understanding, hey, I'm in a really good position right now. There is zero guarantee that things are going to continue like this moving forward. So Showing up, giving gratitude not only for the position, but also for the people around me, I think is a daily task.

46:23 Scott Ingram: Man, you have really figured out something super early in your career that I think a lot of enterprise sellers… I mean, it takes us… I'm going to say me because maybe I'm slow, but I feel like this is a decade-plus type of thing. And we started to talk about this and really dig into this at the last Sales Success Summit. And Evan Kelsay kind of helped with this, just the idea of when When you get into true enterprise sales and you're doing big deals, so much of that work is internal, right? So much of it is the coordination and collaboration between the rest of your team. It's amazing that you have cracked that code so well, so early in your career. And I mean, what I love about what you just shared is part of it is the relationship, but you're also, you know, doing the deal-level work just to check in, make sure everybody's on the same page. And, you know, just doing the work of incrementally moving each opportunity forward and making sure that everybody's taking on their piece. Is there anything more that you can say about that? And where did that come from? Because like I said, it takes a lot of us a lot longer to figure this out.

47:27 Jack English: Yeah, I think it really comes down to a point of necessity, right? It's like when you are running enterprise deals and we're talking deals into the 7 figures, it becomes very clear that either you can try and fail alone, which you will 100% do if you're going in to talk to I don't know, the CIO of the City of New York as a 27-year-old and you think you have all the answers, you're going to find out very quickly that you don't. So having that humility, I think really early on and saying, you know what, I don't have the ego to… I personally don't have to know that every part of this deal was down to my success, my silver tongue, the words I said in the demos that I ran. At the end of the day, we're a company and we're a team. We're coming together to achieve a common outcome. Great. I'm here to just facilitate those conversations happening with the right people at at the right time. So if I have someone way better positioned than me to have a conversation with a specific individual, why wouldn't I take a back seat and let them go and talk about it? Like, I couldn't foresee why I would feel the need to try and take control over that conversation. And really, once I think that's when the penny drops, right, is understanding that you as a seller are really, to the earlier point, and this is a point that has been made by so many folks that have come on your podcast from an enterprise perspective, you are just kind of that middle coordinator. You're the center and I don't watch basketball, so this might be a terrible analogy, but I think the center passes the ball a lot. That's all I'm doing. I'm taking the ball, someone's throwing it to me. I'm finding out who to pass it to next and giving it over there really. And I think that's when we're going back to that 80/20 is understanding that's where the value is in being a great enterprise seller. It's not having the perfect demo or saying the perfect things or having the perfect objection handle. It's understanding what are the 20% of things in a deal that are gonna make the biggest impact to it moving forward. And consistently facilitating that. And usually what I found is putting the right people in the right room together, putting technical experts and putting people that have sat in your prospect's shoes before. We're lucky, as I mentioned, to have local government people on our team. So we've had people that have used the product and sat in the seat. Putting them in the room with my prospect is worth 10, 20, 100, 1,000 times more. Their words are worth that much more than mine as a relatively inexperienced salesperson. That's really a key tool to finding success.

49:31 Scott Ingram: Yeah. So good. So good. All right. You hinted at this earlier, so I'm excited to dig into kind of your information diet. So what does that consist of and when are you consuming it?

49:41 Jack English: Okay. So I've come around to the realization that I think input is everything, honestly, in terms of what you put in your brain is directly correlated with the quality of output that your brain creates for you. And I think this is true whether it comes down to people you associate with, right? You know, the obvious quote, you're the average of your 5 best friends. It's the music you listen to, it's the shows you watch. So I am very, very intentional about putting things in my brain that facilitate the type of output that I want to see. So I try and minimize the input of garbage. And when I say garbage, I mean things that are just either they're media, videos, content, whatever it might be that really just seek to spike your emotions in ways that probably aren't productive for you long term. Music that's a little bit nihilistic and pessimistic, that's not fantastic when it comes to output as well. And I'm a big podcaster. I listen obviously to this podcast. Another podcast I listen to, very different, 30 Minutes to President's Club. I think I listen to yours because it provides some of that strategic reflection on who you are, how you show up for your customers and what you want to be known for. And then, you know, other podcasts like the one I just mentioned for really tactical stuff, right? Just to keep you sharp day to day. Beyond that my favorite podcast to listen to is one called Invest Like the Best. If y'all don't listen to that, I'm throwing in y'all because you're in Texas, Scott. I don't know if that's the correct usage, but if you guys don't listen to that, it's okay. Good. It's amazing. It's an incredible input source of operators and creatives. It'll be people that, for example, built Uber Eats from the ground up. It'll be the CEO from Spotify. It'll be, I think one that I recently listened to was the director of operations at like the Philadelphia 76ers. Listen to content like this, to content like that a couple of times a week, and I guarantee you will feel your mental state, your thought patterns start to elevate. I think it's impossible not to when you listen to really good stuff.

51:24 Scott Ingram: Brilliant. Brilliant. What about the tech side of your world? What are kind of the tools and apps that are central to the way you operate?

51:31 Jack English: Pretty old school on this one. I'm a big Gmail stan, so I went to Outlook once, will never go back. So I use Gmail, Slack, Outreach, and Salesforce. And really everything in my world corrals around that. We're starting to play with ChatGPT a little bit in our company, both from a customer deliverable perspective, which is quite cool, but also just being a little bit creative in terms of how can we cut down some of the more manual research work and outreach work that we're doing with customers. I would also recommend some of your listeners to go and play with OpenAI around not necessarily, let's say, writing emails or developing sequences for you because it's still got a long way to go there. But let's say finding specific pain points for your target persona at your company. There are some really interesting questions and ways you can phrase that to ChatGPT that'll massively cut down on some of that more manual work that you're doing for research.

52:18 Scott Ingram: Yeah, give us a hack or 2 there. Like what kind of question type inputs have you found to be helpful on that front?

52:24 Jack English: So the one we've been playing with most recently is, I can't remember exactly how it's phrased, but basically put your, or asking ChatGPT, put yourself in the shoes or imagine yourself as X persona at Y organization. What are the 3 main objectives that you're trying to accomplish this year? What are the 3 issues you're focused on recently or the 3 biggest strategic risks you might be focused on in 2023? And I think I was actually reading on LinkedIn, I can't unfortunately remember who mentioned this, but you can even go a layer, a step further and say, and format this. You can ask the application format this in bullet point fashion. So then it'll even take the kind of the burden of reading paragraphs out. It'll literally go bang, bang, bang, 1, 2, 3. And you can immediately lift that, put it into a sequence, and away you go.

53:06 Scott Ingram: That is fascinating. It's so interesting how, what a monumental leap ChatGPT was. You know, the thing that's been interesting for me on the tech front lately that I've been thinking about a lot, given that I play on both sides of this, right, is, you know, our growth as humans, right, as we try and get better at sales and improve our craft is incremental, right? Like we're probably not gonna take exponential leaps, especially once you've been at this for a couple of years. But the evolution of technology is exponential. So, I mean, given how big of a leap we've just seen here recently with ChatGPT, like play that forward another 3, 4, 5 years and this is gonna get really interesting.

53:48 Jack English: Yeah.

53:49 Scott Ingram: Yep.

53:49 Jack English: I agree. Yeah. It's something we have to be very open to as well. I think, you know, naturally we can be a little bit hesitant or conservative in our adoption of new technology. That's just a human thing once you get beyond you know, a certain age especially. So always being open and taking the time to understand some of those emerging technologies will pay massive dividends down the line, I think. Yeah.

54:07 Scott Ingram: Yeah. I think you just have to play with it, right? Which is why I asked about kind of the questions and the inputs you're using. I think that's a fascinating use case. So talk about, do you subscribe to a particular sales philosophy?

54:19 Jack English: Sales philosophy. I knew this question was coming and I tried to, I really racked my brain trying to, you know, take this philosophy. How do I align with that? Another one. You know, I've read a lot of books. I've read Gap Selling, I've read Challenger Sale, I've read SPIN and Value and everything in between. I think what it really boils down to is your way is always going to be better than the way. The example being, you know, I can listen to a podcast, an episode of your podcast, and the guy talks about treating customers like they're your own family, and that's the only way to sell, and that's how he's got there to the top. And then another guest will come on and they'll talk about having this really robotic mechanical process that they push prospects through. And it's very repeatable. And that's the way to be successful is just creating kind of that conveyor belt. And at the end of both of those podcasts, you can kind of walk away and go, well, that's how I need to sell, or that's how I need to sell, or that's how I need to act in front of my management. But at the end of the day, I don't think, and my experience has shown that everyone has some unique selling points and a human being is so complex that the best you can ever do is take elements of what other people are doing and incorporate them into yourself. I can read Gap Selling, 100 times day after day after day, I'm never going to be able to execute it like Keenan. And as a result, it's never going to be 100% authentic. I have to take what works from that sales philosophy or methodology and incorporate it into what is just something that's Jack at the end of the day. So there are, for me, guiding posts to use as light in the dark. And I think I have a maybe a sales style, and those… that style is characterized by specific elements and important guideposts for me. But I wouldn't say front to back, top to bottom, there is a defined sales philosophy.

55:52 Scott Ingram: Yeah. Amen. So I think that's kind of, you know, that I hope that's what people take away from the show, right? It's just like, these are inputs, but ultimately you have to take it and you have to make it yours. So Jack, what is your way? What is your style?

56:09 Jack English: Yeah. I hope that I've, let's say, communicated this or demonstrated this on our conversation today, but all about transparency. And it's not necessarily just because, hey, transparency is the moral thing to do, but transparency also equals velocity. Not necessarily the velocity of the deal, the speed of the deal, although it can definitely help, but more even fundamental than that, I think it's the velocity of the exchange of information. Your job as a seller is 100% dependent on the information that you have, right? The information you need to disqualify a deal quickly. To know where budget's coming from so you can forecast the deal, to know the org structure of the company to predict, you know, what you might need to navigate politically. And what transparency does is provoke both parties to share the information that they have immediately. So that might come down to at the end of a call being really transparent and calling out the elephant in the room and saying, hey, based on what I've shared, this doesn't sound like it's really hit the mark on what you're expecting, what you're hoping for. And that's a million-dollar question alone because, you know, your prospect is either going to fall over themselves to now justify whatever value they did see and, you know, what the benefit is going to be of an expanding between both of you. Or if they're not interested, you've just given them a really non-confrontational way to say that and skip the whole, hey, send me some info and I'll let you know and the whole song and dance that zaps our energy as sellers. So transparency, 100% is really important. I'm going to shout out someone, a guy called Charles Mulbauer. He's been on a couple of podcasts. He has a really interesting way of saying humbling disclaimer, which is, hey, I'm gonna ask some really, let's say, direct questions that might otherwise be a little bit uncomfortable, but if you disclaim them in such a way and you kind of tear down the fourth wall and say, hey prospect, I'm about to ask you this really might be uncomfortable question. This is the reason I'm gonna ask it to you, and this is the reason within the context of this whole relationship I'm trying to build with you. I think that transparency is absolute money. The other thing around my style is coming from New Zealand, we're pretty timid people. I like to compare us in Australia to like the US and Canada, right? The US is a little bit more blustery, braggadocious. Canada known to be a little bit more polite and quiet. That's kind of the deal between us and Australia. So some people really like to challenge or control the conversation, you know, to lead their prospects down the paths. I've found in the field that I'm working with, you know, dealing directly with the mayors of million-plus population cities, that trying to demonstrate a particular air of confidence or even overconfidence can be a really dangerous path. These personalities like to see a few things in younger salespeople or younger people that they work with: extreme precision, attention to detail, the ability to follow up consistently and accurately, to work hard and be responsive, but not necessarily to be educated or challenged, which goes against some of the prevailing sales methodologies. So my style can be a little bit deferential. My manager might say excessively at times, but I'm always careful to explain to that earlier point why I'm asking a particular question or to really encourage pushback and objections because I want to create an environment where the prospect feels comfortable asking any question with 100% expectation that they'll always receive a truthful answer in response.

59:09 Scott Ingram: Interesting. Have you read the book The Speed of Trust?

59:11 Jack English: Ooh, Stephen Covey?

59:12 Scott Ingram: Yes.

59:13 Jack English: Have not, but tell me about it.

59:14 Scott Ingram: Well, the way you described your approach and your style just absolutely reminded me of that book. I would pick it up, see if it resonates with you. Okay.

59:21 Jack English: Will do. Perfect.

59:22 Scott Ingram: I don't usually make book recommendations to my guests in the middle, but there you go. I'm serious. Like, I loved that book. I thought it was a, it's not a sales book, but just the way you described your approach was so much like that. So yeah, check it out.

59:35 Jack English: Okay. Any like through line throughout the book that the listeners might be interested in?

59:39 Scott Ingram: It really aligns with your idea that there is a velocity impact to transparency.

59:46 Jack English: Yeah.

59:47 Scott Ingram: Right. And that is kind of what the book is about. It's, it's the speed of trust. Like the more we trust each other. The faster we can go because we don't have to like stop and check and, you know, deal with, with all of this. And actually, this is a really perfect transition point for me because I wanted to ask you about, you know, we all deal with political implications in our deals in one way, shape, or form, right? Like usually it's office politics. You're dealing with literal politics. Like how do you think about that? How do you navigate that?

1:00:14 Jack English: Yeah, there's no secret to it. At the end of the day, it's a fascinating, fascinating world that we work in. So the hard part is that especially in the enterprise space, it's very political, right? So if I'm dealing with a city of 10,000, 15,000 people, the city kind of runs year over year, decade over decade, and the politics don't really matter much unless someone, you know, there's a massive scandal and it turns out the mayor was doing something super shady. But, you know, we're talking about the city of LA here, a client of ours. We're talking about the city of New York. When the mayor changes, the entire city changes. The decks get cleared. The benches get cleared, should I say. Everyone's out, whole new bunch of people are in. So for example, the city of, let's say, Denver, we were working an opportunity with Denver. I think it was around 7, 8 months ago. Well, the mayor, Michael Hancock, he's termed out. So next year he's going to be out of office and so will all of his team. That basically meant that as we're working a deal 7 months ago, realistically, by the time that deal would have concluded, it would have been around now.

1:01:10 Scott Ingram: Right?

1:01:10 Jack English: We're in the enterprise space working 6-month deals, and implementation would have happened in February, and the impact of our solution may not be felt until, you know, February, March, going into April, at which point, you know, they're checked out, they're looking for new jobs. So it's a much different space where 9 months ago we've basically had to write off account for the next 2 years because of the political change that's coming in. Right now, the change in Los Angeles with the new mayor coming in, Mayor Bass, is not necessarily going to be a problem, but it definitely changes where your champions… of course, it puts everything at risk. So not only from a sales perspective, which is the obvious ones going before, like that deal earlier where I'd mentioned actually going before council for a vote, which is super fun. Actually, you know, we have a great solution, the city's been using it for 3, 4 years, and now everyone's leaving and we have to find an entirely new group of people to try and sell again. It's just a crazy world, and there's definitely a reason why people say selling to government is a good 20-25% harder.

1:02:05 Scott Ingram: Yeah. You know, it's funny. I mean, it sounds like it's sort of a double-edged sword, right? Is you're having to deal with all of that change and all of that politics. But I guess the flip side is it's predictable. You know that it's going to happen. Whereas, you know, the CEO or the leader of the division you were selling to leaves and that was not predictable.

1:02:23 Jack English: You're right. You're right. The other thing I think is a bonus as well is, so take Medic, right? We all know Medic. We love Medic. We do use MEDIC. The M for MEDIC is metric that I've traditionally seen it done, right? So you're looking for like a time-bound quantifiable event or something to tie your solution to. We don't really have that in government. There's no profit motive. No one really cares what the costs are at the end of the day. They're not going to run out of money because they get it from us. So we've actually changed the M in MEDIC from metrics to meaningful narrative. And just as, you know, a mayor leaving can provide an opportunity for us to lose our contract and leave, It can also provide some really interesting hooks for us to start conversations. You know, a new mayor comes in and all of a sudden, let's say the city of Tampa is striving to be a zero pedestrian fatality city. Or, you know, take another city and some, you know, councilor was pilfering funds and caused a trust crisis between residents in the city. Well, now they're looking for, you know, radically overnight a way to build trust with their residents. So just as it can be, I guess to your point, it is a double-edged sword, right? You can be out, but also overnight there can be massive opportunities for your solution as well.

1:03:28 Scott Ingram: Yeah. Just absolutely fascinating. And I guess the advantage of selling to larger cities is you've got a lot of press. There's a lot of data coming out about what's going on. What do people care about? You know, what are people voting? How are… yeah, I mean, you've got public council meetings. I mean, it sounds like you actually get to watch the vote on your deal to know if it's going to go down. I don't know if.

1:03:49 Jack English: Yes, I don't know if I would use the word we get to watch. Unfortunately, we have to watch some of them go into the wee hours of the morning. So if you like being up at 1 in the morning, listening to rural council meetings on a Tuesday, then this is definitely the industry for you.

1:04:03 Scott Ingram: Well, that makes for an interesting transition because I want to ask about just how you think about drive and motivation and what it is that kind of ultimately drives you.

1:04:14 Jack English: I think my drive comes down to being super, super interested in understanding how good I really am. And obviously we use external markers as that gauge. When I first started in sales, I didn't know if I was good enough to land a demo with a qualified prospect, but I was curious and I wanted to know if I could. Yeah, I ticked that box and I thought, okay, I wonder if I'm good enough to beat quota 3 months in a row. I ticked that box. Okay, am I good enough to close a deal on my own as an AE? I ticked that box, a 6-figure deal. A 7-figure deal. I think we should all be trying consistently to find the upper edge of our potential and our capacity. Until I fail at something 10 times, 20 times in a row, I refuse to tell myself that I can't do it. You know, why can't I? Unless it's something that, let's say, requires specific physical capacity like bench pressing 500 pounds. There's always a way for a regular person, I think, to achieve something exceptional, especially in sales, provided you have the right mindset, provided you run 80/20, provided you take ownership. That said, the higher you go, the more honest you have to be with yourself and the more time you do have to take sharpening your sword. Obviously, what won you your first $3K deal isn't going to be what will help you close the million-dollar deal. But for me, my competitiveness is really just a curiosity about myself in saying, hey, I was born into this body. It seems like it can do some really cool things. I see that there are some people out there doing way more lauded things, some better things than me. I wonder if the body that I'm in can get up to that. And then if I can't, I want to know exactly why I couldn't and where the gaps were so I can work on those.

1:05:41 Scott Ingram: Is there a current question, a current curiosity? Like, I wonder if I can X?

1:05:46 Jack English: I think like everyone, we have those more, let's say, nuts and bolts desires around our living situation, the money we make, and all of that good stuff. I think specifically for me working in the industry I am, it's really easy to actually see the tangible impact on the work that you have. On people out in the street watching their potholes get filled or watching the process that they deal with their government and be improved. And for me, I think it's not as easily definable as like a dollar amount, but I'm very, very interested always in seeing how many people I can impact through my work. For example, our company, and I wasn't involved in this deal, just wrapped up with the City of London and are going to be building out an application to massively improve the way Londoners, I think they're called, interact with their city around issues of trust and safety. That's a real tangible output that people in my company have put themselves toward that is gonna result in a massive improvement in quality of life for Londoners. So I think having those as your north stars, your guidestones for me is where I'm always focused in all day, every day.

1:06:43 Scott Ingram: Sweet. Sweet. So is there something you believe that the average or typical sales professional would think is crazy?

1:06:50 Jack English: Yeah, I actually was having this conversation pretty recently. It's not 100% mine, but once they said it, I was like, you're totally right. It's that there's not enough leads. We always hear when, you know, it's kind of like locker room talk amongst salespeople. You go on reddit.com/r/sales or some other forum and people are saying, I'm an AE and I was brought into this company, I was duped and there's no leads. We don't have enough leads. BDRs aren't getting me leads. There's no leads coming inbound. There's no leads. I'm starving here. There's always leads. You know, people on this podcast, some of them are working at Dell or Microsoft. They have like 2 accounts and they run a $3 million quota. Dealing with 2 accounts. There's always enough leads. The world is very open. There's always enough money out there flowing in the right direction, provided you can position yourself in a way that takes advantage of some of those currents and industry threads. So I think if you're not seeing the success that you're hoping for or expecting from, and you're putting that down to a lack of leads, I would ask some very hard questions around the way that, or around your mindset looking out into the market. And also your daily activities. Are you really putting in the reps? Are you really going out there and hitting the phones and consistently writing good copy? Because there's a difference between just writing emails and writing really good copy. And I think if you ask yourself those questions, you change your behavior and you do that for a year and you've still got, you know, no leads, then we can have a conversation. But after a couple of months, not accepting that.

1:08:07 Scott Ingram: Yeah. What about the flip side? Is there something that the average or typical sales professional believes that you think is crazy?

1:08:13 Jack English: It's not so much a belief, but I just, I think the level of autopilot that so many people operate on is really mind-blowing. I just see quite often, let's say someone, you know, not hitting their number and not really going away and actually spending, it could be an hour, you know, sitting down and going, what were, going back to the 80/20, I apologize everyone, but what were those really, what were those things that if I was to focus on that went really bad last quarter, that if I was to focus on would dramatically improve my outcome? I think a lot of people just take what they learned. Let's say they felt like they learned a lot in their first year of sales, their first 2 years of sales they had, some reasonable success and they're just running autopilot. They're just running that same script for the next 10, 15 years. And when things aren't going that well, they kind of throw their hands up in the air and go, oh, guess the market's doing this, or, oh, guess I'm in the wrong company, or, guess the product sucks. So many people are having that level of autopilot. So I think if you're one of the very few people, and I think people that take the time out of their day to listen to a podcast like this, not only a podcast like this, but like an hour into a podcast like this, probably indicates that they're operating at a higher level of consciousness around their professional commitment than others.

1:09:16 Scott Ingram: Yeah, I like that. And it's always fun for me to call it out, right? Because I think that there is a minority of sales professionals that maybe aren't on autopilot. Maybe that's the way to think about it, right? Where, look, I know that I've got another gear and you gotta work to get there and to find that. And to your point, they're probably the ones that are listening right now. Like, that's a really good sign. That's a really good step. Then it comes to putting that into action. So let's talk about them. So, you know, Jack, you're talking to somebody that isn't on autopilot that wants to find that next gear. What advice do you have for them?

1:09:52 Jack English: I would say it comes down to critical thinking. I would say be really intentional and critical about the space that you're working in and understand some core truths. I think one of the core truths is money's made in gaps. So gaps between tasks that are really hard and the number of people that are available to do them. Gaps between industry necessities and the number of vendors there are to supply them. Gaps between a company's growth targets and the number of reps that has to meet them, blah, blah, blah. So I think that's an example of, okay, we kind of know that, you know, money is made out of hard tasks, but being really intentional and saying, okay, in my current situation, where are the gaps in the industry that I'm seeing? Where are the elements that our company can solve a problem that not many other people are doing that? In my company, what are some of those tasks that maybe Or what are some of those areas in, you know, within my company? What are some of those areas that our leadership is screaming out for people to take ownership over that there's not enough people or no one's putting their hand up to do that? Be really intentional and be really thoughtful and critical. All of those things, you want to be on the side of the scarce resource fulfilling a valuable problem. Yeah, no, I think be really critical about your situation, about your relationships that you're having, and take that ownership mentality 100% and just ask yourself the hard questions that you probably know deep down as you your head on the pillow at night that you've been avoiding.

1:11:01 Scott Ingram: Yeah. Jack, does this gap approach that you're talking about, does that apply to… because you've mentioned it kind of a couple of different ways… does that connect to your investment philosophy at all, or is that a different approach?

1:11:12 Jack English: I'm guilty as charged. It does not. It's one of those areas that I'm maybe a little bit more, let's say, lazy on in my life. I'm going to use the excuse of being 80/20. For me, the vast majority of my wealth comes from me being really competent professionally. So I've kind of done the calculation that Hey, I could totally spend 20 hours a week reading The Motley Fool, I think it's called, or Yahoo Finance, finding, you know, different stock trades and currency fluctuations and all of that to try and eke out a little bit more profit there. But for me, it's much easier. I throw everything in an ETF right now. I'm crying every day looking at it. I try not to look at it and really pour as much time as I can into leveling up my valuable resource, which is my ability to sell.

1:11:49 Scott Ingram: Love it. Love it. Super clean. So Jack, we've covered quite a bit of ground. I know, I mean, you wanted to come on the show to kind of impart this knowledge for, especially for early career sales professionals or those who were kind of thinking about this path. Is there anything we didn't get to that I either didn't ask the right question or you felt was important to articulate that we just haven't covered?

1:12:09 Jack English: Yeah, I think it's always good to get out over your skis a little bit. And what I mean by that is always stepping into those areas that may be a little bit uncomfortable, you know, to again, break the fourth wall. Coming on a podcast like this, pretty uncomfortable. It's not something that I do every day as a salesperson reaching out to the CEO of an XYZ company or getting on a sales call and engaging in a business conversation with someone. You're never really going to feel comfortable, but 100%, those are the areas in life that you need to be leaning into the most because that's where the growth is found. And that's where, when it comes back to that earlier answer about finding your full capacity, you're never going to get comfortable in something unless you actually step out and get into it and just try it. So I think if I was to challenge anyone and a takeaway for people over an hour and a half into this podcast would be just always move toward that feeling of discomfort and anxiety. And our natural instincts pushes us away from that sometimes, says, hey, you're not ready for that. Hey, you're not good enough for that. But I think the amazing thing about the world is that we're all out here kind of faking it at the end of the day. So, just take a step back and really begin to live the life that you would like to see be lived rather than the life you are living, if that makes sense. I know it's a little bit corny, but really pushing yourself to not see yourself in a grown narrative. Hey, I've been this way for 10 years, so that's the way I always will be. And that's just me, I guess. And I'm never going to change. And so be it. Actually saying, hey, you know what, I actually want to be this person. And I'm really scared because that's going to be a really difficult thing to do. But I'm just going to do it anyway. Because the worst thing that can happen is in this case, Scott tells me as a bad podcast guest, but you know what, I did it at the end of the day, and I'm happy for it.

1:13:38 Scott Ingram: I'm certainly not gonna tell you that. Yeah. 'Cause this is, this has been great. I have really, really enjoyed this. And we always try and end on something really actionable. And I wonder if that was, if that was it or you've got a different thing. So what would you challenge our listener to do over the course of the next week or 2 to improve themselves and improve their results?

1:13:56 Jack English: Yeah, I think it would totally be along the same lines. I think it would be take something in your day-to-day and that could be your romantic life. It could be around your professional life. It could be anything in between. And do something that is a little bit out of the ordinary in the sense of put yourself in a position where you don't feel 100% comfortable, where you… where there is a chance of failure. Just trust that the universe is going to have it in store for you. You're going to have the power to achieve it because I think, like I just mentioned, that's where the true growth comes from.

1:14:21 Scott Ingram: Perfect. Perfect. Jack, this has been an absolute blast. Thank you for taking the time. It's been great getting to know you.

1:14:27 Jack English: You bet. You as well, Scott. Thank you so much. Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.