In one line
Tom Sienkowski, the top sales executive at Reeher, has sold close to $12 million in total contract value over six years selling fundraising software to colleges and universities — buyers with no compelling reason to change — by becoming an industry expert, running a consensus-driven sale across many personas, and being unafraid to fail publicly.
Who is Tom Sienkowski?
Tom Sienkowski is the top sales executive at Reeher, a management and predictive-modeling platform for the advancement (fundraising) teams at colleges and universities. He has been at Reeher for over six years, joining when it was a startup of 13–14 employees and roughly 20 customers and helping grow it to 60–70 employees and 140+ customers. He has spent his entire career in sales — starting at 14 or 15 in retail at a leather-goods store in an Indiana outlet mall, then selling through his time at Indiana University, then joining Enterprise Rent-A-Car's management program in Bloomington, Indiana before moving to Minnesota. He sells organizational change to institutions that love the status quo, using software as the vehicle to deliver it. He was introduced to the show by Mike Bernard, a former VP of Sales & Marketing at Reeher and a previous boss of host Scott Ingram.
Key questions answered
What are the top 3 things that make Tom Sienkowski a top performer? Per Tom Sienkowski (Reeher), on Sales Success Stories, it's being genuinely passionate about what he sells (his prospects, their business, the company mission, the solutions); deep industry knowledge from six-plus years selling into higher ed, a "very, very unique sale"; and, most important, not being afraid to fail publicly — making mistakes in front of colleagues, customers and prospects so he can be corrected and improve. 0:01:09
What does "failing publicly" mean in sales? Per Tom Sienkowski (Reeher), on Sales Success Stories, it means taking your calls at your desk in the bullpen instead of hiding in a private room, so a colleague can hear a mistake and say "let's talk about a better tactic," and it means being willing to tell a customer "I said the wrong thing, I want to correct that." He fails all the time, picks himself up, and learns from it. 0:02:28
How do you sell to buyers who have no reason to change — like colleges and universities? Per Tom Sienkowski (Reeher), on Sales Success Stories, it's a consensus-driven sale where a room of 25–30 highly intelligent people (some with PhDs in data science) all have to say yes — so success comes from understanding each persona around the table, mapping the solution to what matters to them, and defusing the fear that the software will replace someone's job. 0:18:59
How did Tom Sienkowski know Reeher was the right place for him? Per Tom Sienkowski (Reeher), on Sales Success Stories, he had five offers to choose from and took a chance on a startup because its mission — helping colleges and universities raise more money and spend less doing it — connected to his own life as a dad who will someday send two boys to college. Unlike prior roles, he never felt the "two-year itch" to leave. 0:15:05
What is Tom Sienkowski's sales philosophy and style? Per Tom Sienkowski (Reeher), on Sales Success Stories, he subscribes to no single methodology — it's a mix of Challenger, value-based selling, consultative selling and solution selling, adjusted to be nimble because an aggressive style doesn't fit his buyers. He enters every deal openly unsure whether his product is the right fit and works with the customer to find out together. 0:31:13
What advice does Tom Sienkowski give salespeople? Per Tom Sienkowski (Reeher), on Sales Success Stories, for people just starting out: sell only because you love to sell — find a company and solution you're passionate about, and don't waste years trying to fit into a mold. For those further along but not yet at the top: do daily self-reflection, ask every night whether you put in maximum effort and moved the needle, and out-work everyone. 0:37:02
Frameworks & concepts
- Fail publicly — deliberately make mistakes in front of colleagues, customers and prospects (take the call at your desk, not in a private room) so you get feedback and improve; the fastest way to keep getting better.
- The consensus-driven / persona sale — when a room of 25–30 stakeholders all must say yes, you win by knowing each persona, mapping the solution to what matters to each, and addressing the fear that it will replace someone's job.
- Software as the vehicle for organizational change — you're not selling a product buyers are seeking; you're selling change to institutions that love the status quo, and the software is how that change gets delivered.
- The two-year itch — the roughly 18-month-to-two-year point where many salespeople start wondering if they should move on; not feeling it is a strong signal you're in the right place.
- Nightly self-reflection — before leaving work each day, ask whether you put in full effort and moved the needle; if not, do more.
- "You might not be a customer" — being willing to tell a prospect they shouldn't buy (now, or ever) and steer them to the right fit — a disqualification-first mindset most reps would find crazy.
Notable claims
- Per Tom Sienkowski, he has sold close to $12 million in total contract value in roughly six years at Reeher.
- He joined Reeher as a startup with 13–14 employees and ~20 customers; it has since grown to 60–70 employees and 140+ customers.
- His favorite sales story is the biggest deal in company history — a large multi-campus institution he won by going against the company's norm and involving the technical/IT stakeholders, not just the business side. 0:11:16
- When choosing his current role he had five different offers and picked the startup. 0:15:05
- Early at Reeher a single sale meant 5–8 discovery conversations (30-minute calls) with individual personas; now he can address those personas in one presentation. 0:21:56
- His biggest career challenge was a previous role at "a phenomenal company" where he wasn't excited about the product — his flat attitude showed to customers, so he left. 0:13:12
Companies, tools & books mentioned
Companies & organizations: Reeher, Enterprise Rent-A-Car, Indiana University.
Tools: Salesforce, Microsoft Outlook, PowerPoint, Webex, Delta app, Hilton app, National (rental car) app.
Books: The Challenger Sale, The Power to Get In, The Happiness Advantage.
Connect with Tom Sienkowski: LinkedIn.
Quotes
"I'm not afraid to fail publicly. And I encourage everyone to do this because it's the best way for you to continue to improve." — Tom Sienkowski 0:01:09
"We are selling organizational change and software is the vehicle to deliver that change." — Scott Ingram, reading Mike Bernard's note about Reeher's sale 0:03:46
"You may not be a customer for my solution, and that's okay in my mind. I will find the folks that this is the right solution for and the right fit." — Tom Sienkowski 0:34:06
"Sell because you love to sell. It needs to be your passion. ... Don't waste those important years of your life and your career trying to fit into a mold." — Tom Sienkowski 0:37:02
"Arrive early, dedicate yourself to the job, focus your attention. ... And I challenge you, if you don't know something, go and ask the questions and figure it out." — Tom Sienkowski 0:46:11
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, I'm joined by Tom Sienkowski. Tom is the top sales executive at Reeher, And a special shout out to my friend Mike Bernard, who got Tom and I connected. Welcome to the show, Tom.
0:36 Tom Sienkowski: Great. Thank you so much, Scott. Great to be here.
0:38 Scott Ingram: Well, looking forward to digging in and coming back to an organization that is a little bit smaller. We've, we've talked to some larger company folks here of late, and I need to say this episode is brought to you today thanks to the generous support of Story Dimensions, who I'll be telling you about in a little bit. But before we get there, Tom, let's get after this and start with some immediate value like we always do. What do you believe are the top 3 things that have allowed you to consistently be the top performer there at Reeher?
1:09 Tom Sienkowski: Yeah, no, absolutely. I think the first thing being passionate about what I do, and that's not just sales, right? It's my prospects, their business, what they're trying to accomplish, the company mission that we're trying to provide. And then of course, all the solutions. I love it, truthfully. I mean, I think that comes through in my sales to those folks. The second thing would be my industry knowledge. You know, I've been with the company a little over 6 years now, and We sell into higher ed, and it is a very, very unique sale. And being able to become an industry expert and understanding what my customers and prospects need and are looking for, I think, has really set me apart. And then finally, number 3, I think, and I actually think this is the most important one, I'm not afraid to fail publicly. And I encourage everyone to do this because it's the best way for you to continue to improve, not be afraid to make mistakes in front of colleagues, customers, but then have an opportunity, of course, to fix those things.
2:11 Scott Ingram: Well, so that's the one I'm most interested in. I mean, we can definitely talk more about the passion and the industry knowledge, which I think in some ways probably go together, but talk a little bit more about this kind of failing publicly thing. Like, what does that look like in reality?
2:28 Tom Sienkowski: Yeah, you know, I, when I think about it, and I've been in sales for quite a while, frankly, my entire career, but failing publicly, what it means is, I mean, you are not afraid to again, make mistakes in front of people. All too often, I'll see, you know, younger reps or newer reps that are scared to take a phone call at their desk in the bullpen, the pit area, or whatever you want to call it. They want to go into a private room where they can close the door and no one can hear what they're saying or doing. To improve, I would rather you sit there and make a mistake on the phone conversation, say the wrong thing to the prospect or to the customer, and let someone around you say, hey, what happened there? Let's talk about this. Let's see if there's a better tactic or a better strategy Something different you could have said to move that conversation forward. And then failing too, I think, in front of customers or prospects is okay. And I think it should be encouraged. You may not know the answer to everything, and you probably don't. Being able to admit your mistakes and maybe even come back at a later time and say, you know what, I said the wrong thing. I want to come and correct that because I genuinely care about your business, Mr. or Mrs. Prospect, and I want to see you all improve, and I want to make sure you're getting the right information from me. So, that's what I encourage and talk about when I say fail publicly.
3:46 Scott Ingram: That's fantastic. That's fantastic. So, before we get into, I'm going to ask for just a little bit more context around who Reeher is and your role, but I thought I would actually share some snippets of the note that Mike sent me. And so, contextually, we both worked for Mike, or maybe you didn't work directly for Mike, but Mike was my previous boss before he joined Reeher. He was our VP of Sales and Marketing. So, we've got a great relationship. I really enjoyed working with Mike, and he, when he sent the note sort of thinking about you, he said, you know, from my perspective, an interview with Tom would be interesting because we are selling to a group of folks with no real compelling reason to change what they're doing, and we're selling them something they don't realize they need. So you could call it building a category, but I would put it more like we are selling organizational change and software is the vehicle to deliver that change. So what we are doing is pretty unique, but there are also correlations for anyone selling into a tough atmosphere. With a complex product to folks who love the status quo. So, I thought that context would be helpful before you tell us just a little bit more about who is Reeher and what is your role.
4:54 Tom Sienkowski: Yeah, yeah. No, I think that's outstanding. And, you know, you can tell those are the words coming straight from a VP of marketing, stated very well. So, what Reeher is, we provide… it's a management platform for college and university advancement teams. This is the side of colleges and universities that raises money for the institutions. That money can go to, you know, campaigns to build new buildings, endow scholarships for students, faculty, staff support, you name it, is where the money goes. But these are institutions that have been fundraising since the dawn of time and raise billions and billions of dollars. So they have it figured out. They know how to fundraise. And what Reeher provides is a management solution that combines Some predictive modeling to help institutions better target and identify the right prospects they should be focusing their attention on. All the management tools, the dashboards, the data visualization to really help drive the change. And then the ongoing customer success support and training, not only from a tactical standpoint, but also strategically. Where is their opportunity? What is the data telling us from a story standpoint and where these institutions can improve their fundraising efforts? And now we'll deliver via the platform's tools, the web-based software, really how to execute that opportunity and really, frankly, improve your fundraising efforts.
6:19 Scott Ingram: Awesome. Awesome. Awesome. So you mentioned there that there's kind of a story component that you're helping them flesh out. What is that exactly?
6:27 Tom Sienkowski: What the right story is for the institution, I think, goes into… I mean, it's from a fundraising standpoint. These institutions typically know who their top prospects are, the people that are their big money donors. Their names are already on buildings at the institutions. They've endowed large scholarships. Many times, though, you know, the story for us is there is a lot of untapped potential within their current constituency for them to get out and better target. So for us to open that up, help identify who those people are, but also improve some efficiencies from a management standpoint, their outreach to those folks to help maximize their return on their investment there is really where the story comes into play. And then Really using the software to help facilitate that.
7:12 Scott Ingram: Awesome. Well, we'll definitely come back to sort of getting inertia-bound organizations like that to move. And I think that'll, that'll be fascinating. But let's go back to sort of the beginning. You said that you've spent your entire career in sales. Where did that start? Sort of walk us through that and your origin story.
7:31 Tom Sienkowski: Yeah. So it started, gosh, when I was, as soon as I could get a work permit, uh, I think it was like 14 or 15. I was, uh, born and raised in Indiana. So, um, I think it was 14 and 15 at the time. And there was a big outlet mall in my hometown. So I got a job in retail sales, working at a store that sold leather products. So purses, wallets, luggage, jackets, all those types of things. So I did that pretty much all the way through high school, a little bit into early college years as well. And then went off to Indiana University, studied there and had, you know, some jobs, of course, in sales throughout that time. But then As soon as I graduated, was looking for a job to stay in Bloomington, Indiana. It was a great place to be and wanted to put some roots there. So, bought a house and got a job with Enterprise Rent-A-Car, went into their management training program, stayed there for a while, moved up through the ranks. And then, my wife said, hey, if you ever want to have children, we need to move to Minnesota to be close to my parents. And I said, all right, sounds good. So, we put our house on the market. And found jobs up here and been in Minnesota ever since.
8:47 Scott Ingram: Excellent. Now, how long ago was that that you made the move to Minnesota?
8:50 Tom Sienkowski: Oh my goodness, probably about 10 years or so ago.
8:53 Scott Ingram: Okay, excellent. So through that journey, I mean, looking back, if you could do anything differently knowing what you know now, is there any change that you would have made?
9:03 Tom Sienkowski: Yeah, absolutely. And I thought about this quite a bit throughout my career. I think the main thing is I would have dedicated myself to sales earlier than I did. Everything that I did prior to, from a sales standpoint, was just natural. It was really just the art and just came easy to me. I wish I would have spent more time early on in my career reading books, analyzing the process, the science, you know, behind sales. I think that would have gotten me to the top a lot sooner.
9:34 Scott Ingram: Yeah, great stuff. Well, before we talk about your results and what exactly it's taken to get to the top there at Reeher, let me say that this episode is sponsored by Story Dimensions, a SaaS sales enablement company. And as you know, I'm a big believer in the power of stories. And when I saw what they offer, I really just fell in love. So Story Dimensions is the only solution that captures and packages real stories from your customers into easy-to-digest and deliver formats that salespeople can use to build credibility and trust with their buyers. And I have so much confidence in the value that this solution brings to sales organizations that I have taken on an advisory role with the organization. So I encourage you to check it out. Go to storydimensions.com and request a live demo. And that way you can see how they can help you accelerate your sales cycles and close more deals. So Tom, let's talk about those results and just quantify your success for us a little bit.
10:31 Tom Sienkowski: Yeah, I think that's one of the hardest things. I don't like to talk about myself and results, but just give you a big number. You know, typically quickly, you know, from a results standpoint, you know, in the last 6 years or so that I've been with Reeher, have sold now, gosh, close to $12 million in total contract value. Excited about that, especially, you know, working for a company that was a startup. When I joined, we had 13, 14 employees, you know, 20-some customers. And now we're at the point where, you know, 60, 70 employees and 140+ customers. So, I'm really excited about those results that we've had.
11:07 Scott Ingram: Fantastic. And 6 years is quite some time and you've watched the organization grow. What's your favorite sales story from that time?
11:16 Tom Sienkowski: Yeah, well, of course, it's going to be the biggest deal I've sold, but it's an interesting one for the company due to the fact when, when I started there, the company belief is, you know, we sell to the business side of these colleges and universities. We don't necessarily get into the technical side of things at all, which I agree with. It works really well in that favor. We need to have business on board, but, you know, I kept feeling that I need to get the technical folks involved at these institutions in the process because they're trying to many times deliver solutions to problems to the business. And I really feel that our solution can, can help them in their efforts. So, I kind of went around and did my thing targeting some, some of the technical folks at some of these institutions and ended up starting and working to build a relationship with a very large institution, multi-campus system, and, you know, time, ended up getting them on board. And it, you know, to this day, it's still the biggest deal in company history.
12:18 Scott Ingram: Awesome. Awesome. Well, and again, lots of consistency in the success that you've had there. Maybe it was that deal, but what are you most proud of?
12:28 Tom Sienkowski: Most proud of from what perspective? The… just me personally?
12:32 Scott Ingram: Yeah. What are you most proud of against what you've done through your sales career?
12:37 Tom Sienkowski: Yeah, you know, I would say my biggest accomplishment would be, you know, the ability to provide for my family. That's what I look back and say that I'm happy about. You know, we're able to do the things that we want to do, go on vacations, travel, you know, whatever it is. Seeing my family happy, and it's because of the work that I'm able to put in, I think is really my biggest accomplishment.
13:04 Scott Ingram: So far, awesome. Now, what about the flip side? What have you found to be the biggest challenge through your sales career?
13:12 Tom Sienkowski: Yeah, well, it's not in my current role, but it was in a you know a previous company that I worked for… a phenomenal company with a great training program… but I just wasn't happy. I wasn't you know excited about the solutions, the products that I was selling. You know, I'd wake up in the morning and it'd be one of those gosh, oh, I gotta go to work again today. And you know. It got to the point where I felt like my poor attitude and my lack of excitement was being reflected onto my customers and my prospects. And that's just not a good thing, right? So, in that respect, you know, it was, it was time for me to make a change and decided to leave the company. And I think it was the right move, you know, for myself and my career, but it was a challenge because, you know, I learned so much being in that role. It was such a great company to work for, but I just wasn't excited about the product and I couldn't get that passion out out to my customers.
14:07 Scott Ingram: So it's, it's interesting you say that, and I will occasionally share some of the sort of collective insights that, that I've come to understand across, you know, now, gosh, this will, I think this will be our 48th episode, something like that. And what's ironic is I rarely do it on my own show. I go and do it on other shows and other webinars and things like that. But the first thing I always start with is you have to be in the right place, right? You're never going to be the best. If you're not in a place where you, you have that passion. So maybe talk a little bit about how do you know? You know, like, let's say you're, you're not in the right place and you're trying to either find the passion in that spot, or you're trying to find the next thing where you can be super excited about the product. And, and maybe just to put it in the context of like the real world and Reeher, you're, you're clearly passionate about what you're doing now. How did you figure that out and know that this was going to be the right place for you?
15:05 Tom Sienkowski: I didn't know coming in the job search. When it was time to identify a new role for myself, you know, I went out, had many interviews, ended up having, you know, 5 different offers to choose from and said, you know, I'm going to take my chance on a startup company, you know, smaller company. I've never done it before. I want to see what that's all about. But then I also looked at what the company mission was. And, you know, Reeher's company mission is to help transform the way colleges and universities raise money. At the end of the day, we want our customers to raise more money and spend less doing it in the process. So when I saw that, I said, huh, you know, I'm, I'm a dad. I have 2 young children, 2 young boys that someday I'm going to, you know, try to send to college. And the cost of education is on the rise and will continue to rise. At some point, it'll, you know, the bubble will break, but I don't know when that'll be. So I said, gosh, if I can go and get a job where I'm able to help these institutions raise more money for scholarships, put more students to school. You know, first, that's going to help society. We're going to educate more. It'll help the workforce, all that good stuff. But maybe some good karma will come back to me and say, you know, when my kids are ready for school, then maybe there will be somebody knocking on the door to want to give them a scholarship. That's how I chose Reeher at the first point. But typically in my career, what I've seen, you know, from… it's about every, you know, year and a half, 2 years in a job, I start to get that itch of, you know, is this the right fit? Do I still want to be here? Is there something else I should be doing? And I think a lot of sales folks experience that. I did not experience that in my current role. I was still excited to come in. I was still excited to learn more. I was still excited to, you know, teach my prospects about new ways to do their business and new insights that we're uncovering through, you know, research and analysis. So taking all of that, you know, kept me in my role. And mind you, there were always ups and downs. There were days that I come home where I'm not, not necessarily happy with a situation, frustrated, and think about, gosh, is this the right job? But still, then every morning I wake back up and I say, yeah, I'm excited to go and help, you know, my customers and prospects fundraise better. So, well, that's fascinating.
17:23 Scott Ingram: Like the idea of, you know, whatever the, whatever the time period is, you know, call it the 2-year itch, right? Where you're like, you're settled in, you're like, oh, this is really comfortable. Well, maybe this is too easy. You know, maybe there's, there's something more, there's, there's something greener. I think that's, that's sort of a fascinating litmus test. And the fact that, you know, that, that didn't even apply and you blew right through that, that's, that's probably a really good sign to pay attention to. Although what I'd love to understand more, and maybe I'll have to keep asking this question, is how do you figure it out even earlier than that? Right? How do you, how do you figure it out before you get married that you're not going to want to stray from this, this current position. Mm-hmm. Because longevity matters, right? I would have to imagine that, you know, your, your results in years 3, 4, 5, 6 have been significantly more than what you did in those first couple of years.
18:15 Tom Sienkowski: Oh, absolutely. And I mean, coming into selling into higher ed, it's a very different sale than what I'd experienced before. So yeah, absolutely, the longevity, the industry knowledge that I've built over the years It makes it a lot easier and my results are better today than they were when I started. So, yeah.
18:34 Scott Ingram: So let's talk a little bit more about kind of what Mike suggested in terms of this complex sale in a place where there's no like immediate need, right? Like people aren't, it doesn't sound like people are seeking out Reeher like, oh, I need what you offer. You're really having to evangelize and bring them along and implement change in a place where folks are often allergic to change.
18:59 Tom Sienkowski: Yeah, yeah. So, you know, what we do, you know, many institutions may have tried to do some of these things before, from, you know, a data analysis standpoint or building their own tools or, you know, hiring outside consultants to give insight, where Reeher comes in and provides, you know, a comprehensive solution to really help drive their results forward. And everything is combined together with it all working hand in hand. So it's, it's different than maybe what they've done before. The hardest part though about, I think, selling is, you know, I am selling to extremely intelligent people. You know, they work for colleges and universities. The jobs of colleges and universities are to educate. So these are the people that have, you know, PhDs in data science and all sorts of, all sorts of things. So getting everyone aligned in really a consensus-driven sale has been the biggest challenge. And I, you know, I look at reps that that, you know, haven't had the longevity or the success at the company. And I think that's the challenge that they face is unable to get everyone along and aligned that, you know, this platform is the right solution for our organization.
20:15 Scott Ingram: So how, how are you doing that?
20:17 Tom Sienkowski: Yeah, you know, it's, it's a lot of understanding the different personas of the folks that are part of the process, because I mean, this isn't where, you know, typical business, you know, a CEO says, We need to do X, Y, and Z to increase our revenue, and this is the right product to do it. They sign the check, or maybe a CFO signs a check, and you're off and buying. This is everybody in the room. You know, you could have a room of 25, 30 people. They all have to say yes, that this is the right solution moving forward. So really, it's getting to know the different personas that are around the table and really what's going to matter to them in their business. How can our solution map to something that will make their lives, frankly, easier. You know, a lot of times there's fear that what we do may take over someone's job and replace what they're doing. So being able to, you know, combat that challenge and, you know, address that you're not going to lose your job over this, we're going to actually give you the ability to do new things or to evolve your career and, frankly, be hopefully more successful. So it's getting, again, going back to getting to know the personas, identifying who those folks are that are part of the process and getting in to find wins that everyone will experience as part of our partnership.
21:32 Scott Ingram: So when you are sort of aligning with those different personas and the different needs that they have, are you trying to divide and conquer? Is that a lot of kind of one-off conversations to address their specific goals and desires, or have you found a way to, in a larger presentation, just sort of touch on what's important to each of those those groups?
21:56 Tom Sienkowski: Yeah, early on in my career at Reeher, it was a lot of individual conversations. Now I understand the personas of who I'm selling to, and a lot of times I can, you know, portray that in a presentation without even having the conversations beforehand. So, but that's evolved. Early on it was, yeah, I'm sitting down and I'm having, you know, 5, 6, 7, 8, you know, discovery conversations, 30-minute phone calls to understand who you are, what you do, and how I may be able to help you.
22:23 Scott Ingram: So it sounds like, I mean, and it's a process that you probably can't even shortcut. You really had to do it person to person to become intimately familiar and humanize those personas and understand what that actually meant and what people were actually trying to do. And now you've gotten to a point that, you know, you've got this expertise, you can kind of weave it all together and make it work in that larger group setting. Exactly. Yep. You're 100% correct. Awesome. Well, let's pivot and talk about just kind of habits and routines and how you structure your life, starting with just kind of walking, walking through your day. I mean, the alarm goes off. What time does that happen and what happens from there?
23:05 Tom Sienkowski: Yeah. Well, if I look at what time my alarm went off today, it was 5. It was supposed to be 5:15, but I was wide awake at like 3:00 AM for some reason. I think it's just what I had on my plate and things I needed to accomplish today. But typically I'm waking up around, you know, 5:15, 5:30 every morning, you know, get ready, get out the door. I have about, you know, I have a little bit of a longer commute to the office. So I'm about a 30-minute commute in the morning, an hour on the way home. So I try to get to the office early, at least, you know, no later than 7:00 AM is what I'm looking for. When I get there, I have my, you know, my coffee to start out the day and, you know, before anyone else is in the office, then I have a chance to have some quiet time to respond to all my emails that are, you know, mission critical that need to get a response first thing. And then I'm jumping Jumping into meetings, I mean, presentations, you know, discovery, exploratory conversations with folks, and then working to obviously progress deals as well.
23:56 Scott Ingram: And then what about… I mean, is there a particular way that you tend to structure your day?
24:01 Tom Sienkowski: Yeah, I would say when I'm scheduling things, I try to do all my presentations first thing in the morning. I'm a morning person. I'm sharpest in the morning. By, you know, the end of the day, 3, 4, 5 o'clock, it's like, oh, I just want to go home, cook dinner for the family, and relax a little bit. So I try to heavy load my schedule for the, the first part of the day with presentations, calls, and then any remaining follow-up I need to do can happen in the afternoon.
24:27 Scott Ingram: Got it, got it. And then what happens, what happens after that? So you, you, you punch out. So, well, 2 questions. What are you doing with your hour and a half of commute time? And then what happens kind of at the end of the day?
24:39 Tom Sienkowski: Yeah, you know, I'm… a lot of times it's talk radio, it's podcasts, it's things like that. Or sometimes on my commute home, it's a phone call to my wife Because we'll be ships passing if she needs to go somewhere when I get home and I have to take care of the kids. So that's our time to actually talk and say, how was your day? What did you do? What can I help with? What needs to be done? And I think that's important to have a little bit of that work-life balance as well. But every day before I leave the office, I always reflect on my day's work and, you know, say, did I do enough and did I put in full effort? And I think that's extremely important to consider. Because if I didn't, then I need to do more. I still may need to leave at, you know, 5 o'clock that day, 4:30, whatever it is to get home. But I'm going to have to pull my laptop out and I'm going to do some work at home after the kids go to bed or whatever to accomplish and actually feel that I was successful for the day.
25:36 Scott Ingram: Yeah. Now, what about how often are you on the road? I know you're getting ready to travel this weekend, which I hope is an anomaly, but how often does that happen?
25:46 Tom Sienkowski: Yeah, I usually do a trip usually about once a week. Last month I didn't have a whole lot on the calendar, but yeah, this month it's been about once a week, you know, maybe one overnight in that time. So, and I'm traveling all over the country.
25:59 Scott Ingram: Got it. And any particular sort of trip tips and techniques and strategies you've found to maintain your sanity on the road?
26:07 Tom Sienkowski: Yeah, you know, I, I know there's a lot of people that work on an airplane and I don't do that. I try to take however long that flight is, and that's my time for some self-reflection. I may watch a movie. I may fall asleep. Who knows? That's just time that I'm relaxing. Before I go on a trip too, I make sure I have everything done for that visit, that presentation. So I'm not stressing out when I get there. I don't like to run up to the deadline of creating a presentation or figuring out proposals or pricing. That should all be done before I get on that airplane. So I would say just the preparation also is really important.
26:46 Scott Ingram: Yeah, well, that's fascinating. I mean, we'll see what order I end up releasing these podcast episodes. If they're in the order of the interviews, I just did another interview where it was exactly the opposite, right? Like, I've got to work on the plane. And, you know, I think what's important, and I don't know that I've called this out on the show, you know, everybody that is at the top has sort of developed their own approach right, that, that fits them. And, you know, what I want to get across and what I want to help kind of pull out in all of these conversations is just the different approaches. And, and they are different. And is the, is the advice potentially conflicting? Yeah, absolutely. And you have to kind of pull the nuggets that work for you, and you have to try different things. So, you know, maybe you always grind, and whenever you're on a plane, you're in work mode because that's, that's work time. Or maybe you take Tom's approach where it's, no, man, when I'm on the plane, I'm gonna decompress the pressurized cabin.
27:45 Tom Sienkowski: Yeah. Yeah. I, uh, that's, that's fascinating. I think, I think it's true though. Everyone is different and you need to find out what works best for you and your process. Because if you figure that out and don't try to fit into a certain mold, I think it'll reflect to your customers, to your prospects that you know what you're doing and you can lead a process and lead them, you know, to the right solution for their, for their company or institution.
28:09 Scott Ingram: Yeah, great, great stuff. So let's talk about some of those inputs that have kind of formed you from kind of an information diet standpoint. I mean, what, what from a… let's make it a little bit more specific to sales. I mean, what have you listened to, read, and watched, and what's had the most impact on you?
28:28 Tom Sienkowski: Yeah, you know, there's some books and things that I've read over the years. Of course, I mean, I think everybody's read at some point in their career The Challenger Sale. There's another book I read, The Power to Get In. I think that's a pretty good one. Read a book not too long ago, The Happiness Advantage, really liked some of the things in there. But I would say, you know, at the end of the day, where from an information diet standpoint, it really, most of my content comes from other sales professionals. You know, I think about just in the last 2 days, I've had 3 different conversations with, well, one was a fraternity brother that's also in sales, a very successful salesperson that we were just catching up. On his challenges, what's going on, and, you know, my work, et cetera. I had some conversations with a former colleague around some issues that he was facing and wanted my feedback on how he'd handle or how I would handle that situation. And then a former mentor, a former boss of mine, I've had some conversations. So I think that is really where I get a lot of my ideas, my thoughts on how to try and do different things is just really networking with peers and other sales professionals. Love that.
29:43 Scott Ingram: Love that. You know, certainly, a lot of the way that I operate, I mean, folks probably realize that I have a lot of conversations beyond just the official recorded podcast interviews. And, you know, it's one of those things where, you know, what is it, iron sharpens iron kind of thing. You know, when you bounce these ideas back and forth and have good sounding boards with that kind of experience, I think we all get better. And certainly, you know, the type of community that I'm hoping to continue to foster around the podcast and certainly the, the Sales Success Summit and the things that we're, we're doing from that perspective. What about tools and apps and, and things like that? What, what helps you the most in your day-to-day?
30:24 Tom Sienkowski: Nothing out of the ordinary. I mean, you know, it's Salesforce, it's my, you know, Outlook, PowerPoint, Webex, uh, you know, some email tracking tools, things like that. From a travel standpoint, it's my Delta app. It's my Hilton app. It's my national rental car app that keeps me, uh, all aligned. But there isn't anything that, you know, stands out that I, I couldn't necessarily live without. I mean, I need to know who to call. I need to, you know, have my, my things for a presentation, and I need to, uh, get on the road to, uh, visit folks.
30:53 Scott Ingram: Yeah, sounds like you're maximizing your loyalty programs as well. You have to.
30:58 Tom Sienkowski: You have to be loyal when you're traveling a lot.
31:00 Scott Ingram: You'll get more out of it in the run. Yeah, great stuff. So Tom, is there… I mean, we, we talked about some of the books and, and some of these other things. Do you feel like you subscribe to a particular sales philosophy?
31:13 Tom Sienkowski: Oh gosh, I'm gonna say no, nothing specific, because I think it's a combination of quite a few actually. I mean, it's, it's things like the Challenger Sale I think is ingrained in some of my work. It's value-based selling, it's consultative selling, solution selling, all mixed in together. Is really how I, you know, organize my sales work and my process. But it all goes back, since I'm selling into such a unique environment, I may not be able to be really, really aggressive in a sale because the personas don't match up to that style. So I really need to adjust and be nimble in my approach and do what's best for the customer in that respect. So I jump around through a lot of different sales philosophies. Fees.
31:58 Scott Ingram: Yeah, that makes sense. How would you describe your style or your approach?
32:03 Tom Sienkowski: Yeah, I think the biggest thing is I come into a situation thinking, I really hope this is the right solution for that customer. But I want to get down to the facts to determine together if a partnership makes sense. So in my mind, you know, it's different than what a normal, you know, salesperson would do that's selling, I don't know, some type of commodity product, right, that every business has, and every business needs. Well, Let's say copiers, right? So everybody needs a copier or a printer. You know, you can go into that environment and, you know, sell that product. I'm in a little bit of a different, different environment. So I go into this saying, this may not be the right solution for this institution, but I want to determine if that is, and I want to be able to check the box and say, it's not, you know, it's not the right fit today. Maybe it's the right fit in the future, or maybe it'll never be a fit, but let's figure that out together. And that's the way I think we'll have a successful partnership.
33:01 Scott Ingram: Awesome, awesome, awesome. So from a motivation standpoint, what motivates you? How do you think about motivation in general?
33:09 Tom Sienkowski: Yeah, so motivation for me, 100%, it's my family that motivates me. You know, I love, you know, seeing the look on my kids' face when I take them to Disney World or, you know, say, hey, we're going on a cruise, guys. How excited are you? That emotion that they give to me motivates me to work harder. And it's also getting the point now, you know, my kids are old enough where they're, you know, wanting to do chores to earn money. And, can I do more work, Dad? How else can I earn money? And we're talking about, you know, hard work and dedication to whatever you're asked to do will help you be successful. So, being able to then teach, you know, my boys that work ethic, I think, is important as well. But it's really my family. Family. The only thing that motivates me to continue to get better.
33:55 Scott Ingram: Beautiful. Love that. Now, is there something that you believe or something that you do that the average salesperson would think is crazy?
34:06 Tom Sienkowski: Something that I do that the average salesperson would think is crazy. You know, I think it's my mindset of everybody might not be a customer for what I'm selling. And I think, you know, most of the time, you know, a sales rep is, I want to sell the solution that I have. So I'm to figure out a way to sell it to them. I'm going to demo, I'm going to go in and pitch the product. But for me, I, you know, you may not be a customer for my solution, and that's okay in my mind. I will find the folks that this is the right solution for and the right fit. So I think that some reps would think I'm crazy for, you know, telling people, I don't think you need to buy that today. I think you can buy that a year from now. I think you should buy this solution from us or vice versa. So I do a lot of that in my sales, but it's always come back in a positive way for me, saying, you know, now's not the right time for you to buy X, Y, and Z from us. I think you should buy A, B, and C instead. And then maybe in the future we can add in this other functionality or this other work that we're gonna do with you. And it's always, it's always paid off taking that approach for me.
35:09 Scott Ingram: Well, and I think that's a pretty common trait among top performers because I think the reality is if you don't do that and you're not picky, you're, you're basically forcing deals and they're low probability deals anyway. So you end up spending so much time that you could spend Spend on real opportunities, and and some of that just comes with with maturity. But I I think that's that's solid advice.
35:32 Tom Sienkowski: Yeah, and you can always. I mean, at least for me, you know, I'm able to sniff out early on in the conversations if someone's going to be serious. You know, on the the prospect side of things, do they really want to review and get into a buying process? If not, again, that's okay. We'll I'll find the right people that want to be a part of this and actually want to to move forward. So if If you can sniff that out early on in any deal, I think you're gonna be way more successful in the long run.
35:58 Scott Ingram: Yeah. Fantastic. What about the flip side? Is there something that either the average rep or even just call it sort of the sales dogma that's out there that you think is just nuts? Yeah.
36:10 Tom Sienkowski: You know, I think the average rep is, we talked a little bit about it in the last question there. It's the average rep just wants to go out and pitch and show a demo of, and thinking about software. It's, I want to just go sell and show the product right away, when in actuality, you don't even know what challenges or needs that customer has. So perhaps take some time on the front end to understand that, get to know the folks a little bit before you start shoving product, shoving product at them. So I think that's, that's something that the average, you know, the average rep would, would kind of lean towards.
36:46 Scott Ingram: Cool. So this is kind of the soapbox advice-giving section, and I like to break this up into a couple of pieces, starting with the advice that you would give to somebody that's just getting started in their sales career today. Hmm.
37:02 Tom Sienkowski: I would say first and foremost, sell because you love to sell. It needs to be your passion. You need to find a company, a solution that you're passionate about. I wish I could have done that really early on in my career and knew that I wanted to be a, you know, successful salesperson right away. So I think that's one of the first things I would always tell someone new in their career. Don't waste those important years of your, of your life and your career trying to fit into a mold. You know, a lot of people will get into sales because they think, oh, I can make a lot of money in sales. So that's why I want to do it. And that's what is just the only thing that's motivating them. If it's not the right fit, if sales isn't for you, there's many other things you can do out there where you can make a lot of money and go and find that. So I would say, if you're going to jump into a sales career, make sure it's something you want to be passionate about. You want to be a student of it. You want to learn and continue to improve for your entire career. And again, no one's perfect. You will never be an absolute expert. It goes back to my comments around failing publicly. You still need to do it. I fail all the time and, you know, pick myself up and learn from it and continue to refine and get better at what doing.
38:15 Scott Ingram: Great stuff. Now, what about somebody who is further into their career? So they're, they're some number of years in and they're, they're doing okay, but they're not at the top. What advice would you give to them to take their game to the next level and get to that number one kind of top 1% position?
38:31 Tom Sienkowski: Yeah, it goes back to the thing that I do every day before I leave work when I reflect on the day and say, did I put in, you know, maximum effort and did I really move the needle in the right direction? Direction, you know, for myself and, you know, for my solutions, my customers, etc. So ask yourself that, because I feel like a lot of times, you know, those average reps are the ones that just aren't putting in enough work, truthfully, and not working hard enough at it. You know, I come into it, I want to outwork everybody, and I want to, uh, be the best at what I can do and what… and things that I can control, I want to make sure that I can control them properly. So I think that average rep just needs to do self-reflection. And then, of course, it's also maybe reflecting on where you're at in your career. Are you with the right company? Are you selling the right solution? If not, make a change. Go find out, go find the right thing for you.
39:23 Scott Ingram: Yeah, well, especially, especially in this market, my gosh, opportunities abound. There is no shortage of great stuff out there. Tom, what would you want to know about the top sellers in other organizations?
39:37 Tom Sienkowski: Yeah, I mean, these are things that, again, I'm always asking friends, former colleagues, et cetera. It's, it's tell me more about your process. How do you things, how do you help your prospects find value in whatever solution you're selling? How do you deal with objections? I think it's all the standard things, but every industry is different and every product or solution you're selling is different. So I feel, you know, there's things that we can all learn from one another. So for me, it's, it's just trying to dig into those top sellers and is there Is there even a small nugget of information that I can take from them and then use that in my day-to-day work? I want that information and that knowledge. Yeah, great.
40:17 Scott Ingram: And I guess we didn't really dig super deep into your own process. I mean, walk us through that. What is that? What works for you? Yeah, yeah.
40:26 Tom Sienkowski: For me, you know, it starts out with, I just want to have a conversation to understand, you know, who the prospect is, what they're looking for, what are their challenges, their gaps, their needs. What does success for them look like and for the institution that they serve? And then, you know, introduce them first and foremost to the offerings that we have, give them an overview of who the company is, who I am, and, you know, some of the success we may have had with some other institutions. And then if there's, if I uncover something that, you know, in that conversation where I have a solution to their problem or their, our product can help them, then I'm going to go down into, you know, setting up presentations. Getting the appropriate people involved in those. Um, I'm probably hopping on an airplane, uh, to go visit some folks and, uh, you know, take it from there.
41:18 Scott Ingram: Beautiful. Who is… it sounds like you're, you're having a lot of these conversations. So who is the most successful salesperson that you know personally?
41:28 Tom Sienkowski: Yeah, I don't know if there is one individual person that I would say is the most successful because I would go back to, you know, how do you quantify success? Is it my friend that makes the most money? Is it my friend that's the happiest in his life? Is it the friend that has moved up the ranks really fast? So I don't have one single person I think that I would say is the most successful. I go back to, you know, I want to take a little bit from everybody. I want to take and learn more from that person that's, you know, making the most money, or I want to learn more from that person that progressed in their career really far. How did they do that. So I don't really have one single person that I would say is the most successful.
42:09 Scott Ingram: I love that answer. And it just, it makes me think about all of the conversations I've had with this show because, you know, it's like asking me who's the most successful salesperson you've interviewed. Like, well, to your point, it really depends. But I guess I should ask more often, like, how do you think of success? Like, what is success to you? Hmm.
42:28 Tom Sienkowski: Success. That's a really tough question, I think, to answer. You know, success to me is looking back at my work and did I make a change? Did I do something that's going to impact the greater good of society? Because that's the industry that I'm working in. So if I'm, you know, for me to be successful, if I'm helping institutions improve their fundraising efforts and I can see a noticeable change there, I can help our company grow. I also look at success for myself of You know, when I started in a small company, you know, we only had 13, 14 employees, and now it's up to, you know, 60, 70 folks. I can say, wow, because of my sales efforts, we're able to grow as a company. New people are able to get jobs. So for me, I look at that as success. And then, you know, feeling like I'm an industry expert when I'm talking with, you know, with customers and prospects, I think is also great.
43:29 Scott Ingram: Yeah, you know, it's funny, that growth element is so interesting and fascinating. And I think I actually touch on this this in one of the stories that I wrote for the Sales Success Stories book, because for me, you know, one of my kind of guiding values is about contribution, and that contribution is at every level, right? It's a contribution to my clients. It's a contribution to the organization I'm working with. It's a contribution to my family. You know, it's all of those things, and I do so much better in much smaller organizations than I do the large organizations because of that line of sight visibility. Like, I'm not… I mean, I've worked for ADP and Oracle and companies where it doesn't matter how much I sold. I mean, I, I could have done 900% of my plan, and at the end of the day, I'm like a rounding error on a rounding error when it comes to what they're reporting to the street, right? Versus being in a small organization where I have 100% line of sight to… I'm I'm me and moving this business forward and just feeling that contribution and knowing that you're impacting so many other areas of the organization. So, you know, I think it's an important dynamic for people to consider is what's not just where are you going to… what are you going to be passionate about from a solution set, but what's that right kind of cultural fit? And I don't know that you know it right off the bat, right? I think you have to kind of experience it and be part of an organization where it's like, Oh, I like it better when there's like one guy between me and the CEO versus like 8 people. Absolutely.
45:10 Tom Sienkowski: And one thing I did, you know, early on in my career with Reeher was, you know, I wanted to get to know my coworkers on a personal level. You know, I wanted to know the people that were building the software, you know, the people that are working in finance and accounting. Like, I just, I just genuinely want to get to know them. Them. I feel like that has really helped me in my career there. Because if I have a question or need some help with something, I have a network of people internally that know, that are building the solutions I'm trying to sell, and may know it more intimately than I do, that I can reach out to. So yeah, I really enjoy that. And I think that has really helped me to get to where I am with the company.
45:52 Scott Ingram: Awesome. Awesome. Awesome. Well, Tom, this has been fantastic and a lot of good talk. Now I want to translate it to action. So the person listening to this, I'm hoping that you can give them a challenge, something they can do over the course of, say, the next week or the next 2 weeks to improve themselves and improve their sales results. What would you suggest that they do?
46:11 Tom Sienkowski: I would say first and foremost, arrive early, dedicate yourself to the job, focus your attention, your time specifically on that. I understand work-life balance, and I think that's extremely important, but you need to focus your attention that this is the most important thing is that I'm trying to move the needle. I'm trying to progress deals and I'm trying to sell. So I think that's the first thing. I also think it's important, you know, work to become an industry expert. Work to understand your competition, who you're selling against, what your customers need, your solutions that you're offering. And I challenge you, if you don't don't know something, go and ask the questions and figure it out. You'll be much better off. And then also, it goes back to my point of failing publicly. Go and make mistakes. It's okay if you make mistakes. I'd rather you do that so you can learn from it than think everything's perfect and keep going down the same path. So those would be some challenges I would put forward.
47:14 Scott Ingram: Beautiful. Tom, is there a public mistake? I don't know how to ask this. I'm inclined to ask if there's a public mistake you're most Or maybe it's the most embarrassing. I mean, what give give us your favorite example of one of those public mistakes that you've made?
47:30 Tom Sienkowski: Oh man, I I mean I don't know if it's you know one big one, but I mean I think it's every day. You know you make a phone call and you leave a voicemail. You'll hear me often. I hang up that phone and say, "Gosh, that was a horrible voicemail." Like I could have done better in that voicemail. My colleagues are all hearing me say that about myself, so hopefully they're learning like oh maybe I shouldn't. Say that? Or, oh, hey, Tom, what if you said this instead? I think that's an example of failing publicly. Or, I mean, it's also when you're in a conversation with a, with a customer. I mean, it's happened to me before where I'm going down a path full steam ahead that, yep, this is the right thing to do. Yes, our company can do this, that, and the other for you. And then come to find out, I was completely wrong. So going back to that, that prospect and saying, I made a mistake here. This is what the actual offering is, or this is how we can help you. I mean, that has, that's come to come, came up numerous times in my career. And, uh, I think it's a great learning experience to, uh, to get better. So much goodness.
48:31 Scott Ingram: So Tom and I are recording this episode a couple of weeks in advance of its release date. So as much as future Scott would love to give you an update on the Sales Success Stories book project, present-day Scott doesn't know what that looks like. So I'd encourage you to get on the mailing list and that is where all of the latest and greatest will be. You can do that at top1summit.com/list. Top1.fm, T-O-P, the number 1, dot FM. And when you do that, the first welcome email also has instructions for how you can get your hands on any one of the 12 videos from the Sales Success Summit. So again, just jump over to top1.fm, get on the mailing list, and I promise good things will happen from there. Thanks for listening. And Tom, thanks again for joining me today. Absolutely.
49:12 Tom Sienkowski: Thank you so much for having me, Scott. I appreciate it. 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.

