The Exit Engine Podcast Episode 45: Meet Jennifer Cresswell
20 Jun 2025 · 58 min
Jennifer Cresswell, founder of ThoughtGrow, breaks down her four-pillar framework for exit readiness: structure, team, process, and culture. She explains why communication often breaks down between founders and their teams, how fractional COO roles help founders scale without over-hiring, and why culture must survive the founder's exit.
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Welcome to the Exit Engine Podcast, episode 45. Welcome to the Exit Engine Podcast. My name is Joe Stapleton. I'm here with my partner in crime as usual, Mr. John Kniff. John, how are you today, man?
I am well, Joe.
Excellent. Good to see you. Uh, we got another great guest today, John.
I'm psyched. Yeah, definitely.
We're going to talk to Jennifer Cresswell. So Jennifer is a founder and principal of— she's got a company called Thought Grow, which is really cool, by the way. It's a great name. She helps business owners solve problems faster during times of uncertainty to create lasting legacies, focusing on strengthening what she calls a business's 4 foundational pillars: structure, Team, process, and culture. Jennifer combines her love of problem solving with a broad skill set and diverse experience across leadership, operations, business strategy, and communications. Whether making a business attractive for acquisition or creating stability to support a growth-focused future, Jennifer truly enjoys working with business owners to define and realize their ultimate visions. Jennifer, thank you so much for being on the, on the Exit Engine podcast today.
Thanks for having me, Joe and John.
I hope that was an appropriate introduction.
It was. Thank you very much. It's always, it's always a pleasure to hear back what others think of you and you think of yourself. So it matches there. So, thank you.
No, I'm glad it's, I'm glad it's aligned. Look, we, we are fascinated by what you, what you do. And again, this is, and our audience should be too. And here's why. Because what you're, what you are doing is that you have got this kind of interesting crossover between operations and really the rest of the business, right? And so one of the things that we talk about all the time on this podcast and in general is that your operations, the way that you are conducting business, is obviously a key to the value of your overall value of your organization, right?
Absolutely.
And how you are able to set that operation up for exit success, right, is a key key point in getting there. Your ability to— your sellability, your ability to sell your company at all. Forget about what the value is, but to sell it at all is highly dependent on your operations and really the marriage between those 4 pillars that you mentioned. Right.
Absolutely. I think that's a key thing. Right. So if you're going to sell your business, you're likely selling and not going to be there anymore. Maybe there's a period of time where there's a crossover that can often happen with a lot of sales. But ultimately, your business needs to run without you. And if you don't have the proper structure, you don't have the right team, you don't have process to amplify efficiency, from that standpoint, nobody's going to buy it. And it's funny, I've had conversations with clients who are, let's say, process-averse, right?
Mm-hmm.
They're like, we just like to do. And I have an engineering background, so I love process. I also highly value people. So it's a good Good place for me to be with these folks are like I hate process. I said, if you got hit by a bus tomorrow, which I hope would never happen, if you have process, your company might be sellable. And they go, what? I'm saying yes. If your top employees leave and you have process, your company might be sellable. Notice I don't say definitely will be, but process process that works. that has purpose, if you've got that and you've got the right people, that's only going to increase the, the exit that you're going to be able to achieve.
Yeah, it's so funny about process because I agree with you, Jennifer. I, one of my jobs in the recent past was strategic initiatives, and that was involving like process, like around CRM for sales. And it's so funny how some people just don't value it at all and they don't, they honestly don't understand what it is. Until sort of you explain what you mean by process.
I think you're exactly right, John. And everybody, especially right now, I think a lot of people are like, we're going to plug AI in. If you don't know what you need to do and you can't replicate it, AI is not going to help you. At least I don't think so. You can tell— yeah, eventually, maybe. But you got to start with knowing what your process is, and then add technology and tools. There's a quote out there. I feel like, feel like it might have even been Bill Gates who said it. So forgive me if that's not the right person, and I hope I give proper accreditation. But it's, if you add technology to something that's already efficient, you'll amplify the efficiency. If you add it to something that's already inefficient, it amplifies the inefficiency. And you need someone, whether that's you, someone on your team, an outside consultant, to help you make sure that your process is efficient before adding things that could muddy the waters, so to speak.
It's a really good point because we know there's all this information, obviously, to talk. AI is a huge thing. AI is a large part of everybody's business already right now, or at least it should be if you're harnessing it the right way. Automation in general, right, is also a big, you know, kind of hot-button item right now. And one of the things that we've learned, probably the hard way too, is that it's a matter of automation. You can only automate things that you actually need to automate, right? In other words, if it doesn't actually speed your process, if it doesn't actually help you save some kind of time or get some kind of efficiency, then it probably shouldn't be automated.
That's exactly right. You need to find that right balance. You need to figure out what's going to— and sometimes it's defining the process, living with it in a manual or semi-manual way to make sure that it works.
Yes.
Right? You really need to test that out. And then the other thing I find a lot of companies don't do is they put a process in place and they never go back to figure out if it's still serving that same purpose that they intended. Now, I also run into companies who tinker and they're like, we'll change this this week and we'll change this this next month. You can't do that either because then you never know if it works, right? So there's that, there's that balance of do you review quarterly? Do you review semi-annually or annually? It depends on the process. It depends on the business, but you need process in order to scale.
Yeah, so true.
No question about it. It's a huge thing. So we always talk about testing, optimizing, and scaling, right? Because it's about picking the area that you want to test, setting up a discrete test too, by the way, which is like, again, Have you actually done that, which most people neglect to do as well? It's like, I'm testing something, but are you testing it in a discrete way that's allowing you to be able to separate out results or make attributions where they're appropriate, right? Then the ability to be able to, you know, to be able to optimize whatever you have found to be working, right? Only then are you ready to be able to scale it or bring it out to, you know, whatever level that you can, you can, right?
That's exactly right. And I would argue that it doesn't just apply to process. I think it applies to people too. And I think that mentality of, you know, you have a team when someone— when you start a company, you both know this. I know this. You have that, that team, that first couple of folks that you're working with. Right. And then as you get bigger, you add more. As you get bigger, you add more. Sometimes you promote from within. Sometimes you bring in skill sets from outside, etc. But you need to also continually evaluate your people, their skill sets, how they're doing, because so many times you also see in companies who have grown from the ground up and are successful, there are people in leadership positions that shouldn't be there.
Yeah.
Not because they're not great people, not because the company can't use them, but because they're in the wrong seat. And I— and it's You have to look at that too, in building the right leadership team to grow and then building the right leadership team to scale. And I know you both discussed this on another podcast episode recently, but love to hear your take.
Well, yeah, the, yes, because what happens is, as you described it, is you either take over, either you're growing a business or you come into a job and you've inherited people. Right. And you look at the, you know, I I like the right people, right seats sort of description. It's like you may have the right people and they're like— and my old boss used to say, you have the right people on the bus. They're just sitting in the wrong seats.
Yep.
And sometimes they're in the right seats. But yeah, if you have the wrong people and they've sort of— they've been elevated to these leadership positions and they're just not there, you're not going to be successful. You're not going to be successful. They're not going to be happy. Because they're in the wrong position. They don't know what they're doing. They don't know how to communicate. And it's a bad situation for the company and for the individual.
I completely agree. And I think you touched on a really important point, John, about communication. And I think that's where, believe it or not, as much as I love solving problems, a lot of times my clients come to me and I'm like, that's not a business problem. It's a communication breakdown. And they don't— they're like, no, but you don't understand. I'm like, I do understand. You're saying this, they think this. And they go, oh, really? And I realized early in my career that I just had this way of, I put things together. And that was one of the first places. I was working at an agency. It was kind of a marketing consulting firm. And they tapped me to be the head of sales, which I looked at them like I was crazy. I'm like, no, no, no, no. They're like, no, we want you to do the strategy. What are we selling? How are we pricing it? How are we incenting people, et cetera? So as part of that, I was working with the lead consultants and they would come to me before they'd have to meet with the CEO. And they'd be like, this is, this is what I, this is what I'm going to be talking about. And I was like, do not say that. And they looked at me like, why not? I was like, I know that's exactly what's happening. You need to say this instead and tell them this is, tell him this is what you're going to do. And they're like, but if I just— I said, no, say it this way. And they were like, and they'd leave my office and they'd go talk to the CEO. And they come back like, it worked. He was happy. I said, I know. So keep doing what you're doing and just remember to use certain language because that's what he needed to hear, even though they were doing the right things.
Well, it's so funny. My contention, and Jo's heard this a million times, is like communication is the biggest problem in any big organization.
Right.
And not so much like it's, it's like written like that, that people don't understand it, but it's they can't take what they've read and sort of translate it either share it with their teams or truly understand what is meant, right? It's either the reader or the writer has to work in a communication. And if you're the, you know, if you're the reader, you know, or if you're the writer, do you want someone to work at your communication? That was given to me by an old colleague of mine, but I thought that was brilliant, is work on your communication or the reader's going to have to work on it.
And if you're in a leadership role, your reader is not going to work on the communication. They're going to take— they're going to interpret it based on their background, based on their experience. And so you need to be thinking about your audience? And, and from that perspective, are you talking to your board? Are you talking to prospective— oftentimes the message is the same message. It's just phrased in a different way and you use different terminology. Um, the other big thing I find that especially founders who have grown a business is they love to get in the weeds because oftentimes they started and they were doers, right, before they innovated. And most of the time, the person buying the company, they don't want to hear about all these little details. They want to hear about how much, who are you, you know, how many clients do you have, what kind of money, what's the trajectory, etc. They care about the higher level stuff. And it's hard sometimes to get out of that mentality, but you have to. And so you got to work with a communications coach, just work on your communication in general to Right-size your message. And again, I have a communications background too. I know engineer communications don't always go together, but—
It is an interesting mix, Jennifer. Like, it is, you know, not, not common.
No, no, it's not common. Interestingly enough, I worked with another engineer communications program to grow and sell her agency. So it's, it's— I've found like individuals, but most people have not.
It is definitely not something you come by. There's no question about it. And we look at personality types and all those things, you know, and those In all those different ways or whatever. It's like, it's, this is not, these, these two things do not normally go together, right?
It's true. It's true. And I think that's another actually great point that you're bringing up, Jo, is personality types.
Right.
So I do a lot of fractional chief of staff work, I call it. Could also be akin to fractional COO. A lot of business owners, at first when they hear fractional, although that's definitely become more a commonplace term now, they're kind of like, oh, well, that person's not dedicated. Then you haven't found the right person.
Right.
And I think personality matches when you're hiring fractional, even when you're hiring full-time. It's working style, it's personality, and it's— there's just something where, you know, if you connect with someone or not. And it doesn't matter how great they are, what their pedigree is, what their skill set is, how many times they've done it before. If you don't connect with them, you may not be successful in your goals. And I think not enough emphasis is placed on that sometimes.
But yeah, no question. And I think, again, getting back to how this, you know, how this contributes to the overall value and saleability of your company, right? The notion of being able to, if you can show not only that you've got the structure, meaning, again, you've got the right, you've got the right organization, you have the right setup to be able to do the business that you're doing as efficiently and effectively as possible.
Right?
Then you've got the right people in the right place, right? Which, which when you have that makes your structure better, makes your operations better, makes your process better, right? You've got the process part, which is obviously this is the way we do X, Y, and Z. It's repeatable, it's tested, it's as efficient as we can possibly make it. It's automated if it has to be. It's not when it isn't, whatever. Then you've got the, the, the pe— the, um, sorry, the stat— the, the, the culture part. And that's what I wanna talk about for a second because—
Mm-hmm.
I think this is such a huge piece of what happens in business. And again, anytime you're talking about human beings, right? And we always laugh whenever human beings come up, even though we're all human beings. But the idea of being able to have a group of people who— a team, which is what this is, right? I mean, you talk, we use the same analogy about everybody kind of rowing in the same direction. And that's, that's the that's what you want to have, and you want to be able to demonstrate that when you have a buyer at the table, right?
Yeah, absolutely.
And, but the, but the cultural thing, I've always heard that, that you can't really— like, culture happens, and it's one of those things that happens whether you're trying to make culture or not, that culture can't really be manufactured, and that at the same time, that every company is actually the culture of its founder. Like it's the person takes on the personality of its founder. Have you found any of that to be true? If not, why not? And what are your thoughts on that culture?
So some of that, yes. Some of that, no. And I'll start with the no. I do think that you can change and drive a culture because I look at culture as how a company is making decisions. And I think as a company grows, how your decision-making process, who's involved, who has the authority and the responsibility to make those decisions, I think that changes. Because when you start from the ground up, sometimes that the founder is making all of the decisions.
Yeah.
They're telling everybody what to do. And then as they get a little bit bigger, maybe they have a number 2 or someone else or a trusted person that they're like, well, you can make these decisions, but everything else still comes to me. Eventually, when you're gonna sell your company, you can't be making all the decisions. You have to have a decision-making process. place. And I think that that's what that change from where you've got the decision-making structure that exists to a decision-making structure that will survive you, so to speak.
Right.
That's when cultures sometimes change. And it is inevitable because there's not as much control by the original business owner. I think a lot of companies do take on the cultures that— so now we'll go to yes, right? So I do think companies take on the cultures of their founders. I also think that founders, as I said earlier, should not apologize for the culture of their company. In fact, in some cases, I wish they were more outwardly like, this is how we work, this is how it is. I read a long time ago— not a long time ago, Maybe a couple months back. I think they were talking about, I think it was LinkedIn, might've been a different, different organization. But when they were starting everything up, they expected people to be working. I won't say round the clock, but almost round the clock. And then they realized, you know, you were going to be giving up a lot with your family, et cetera. But those early options to what they grew up to, there's trade-offs to every decision you make.
Sure.
As they got bigger, they said, okay, we want you, you know, I'm not saying complaints, but family time.
As soon as you have, as soon as you're big enough to have an HR department, that has to be right.
So they're saying, okay, we're going to prioritize family dinners, like making sure you can be home, have your dinner, but then we expect you to go back to work. And to be fair, if you don't want that, you can find a job elsewhere. They didn't say that. That would not be a message that you communicate to your employees. But I think if you're clear about what the expectations are, and I always believe in setting expectations, then people have the choice as to whether or not they want to do that, whether or not they want to do that for a period of time. And they know that they're going to have to find a different solution. And I think that changes throughout your life. You know, if you— I'd love to hear your thoughts on that.
Well, what it leads me, you know, you talk about change too, right? Leading people through change. So that example where you have a culture where it's You work, you go to, you have dinner, and then you go back to work. Like, how do you, how have you worked with clients to alter their culture so that they can either grow or sell themselves or, or do something along those lines?
So some of it goes to really trying to dig into what you want X, what's the Y behind it? Why is that so important to you? Before the pandemic, I worked for a company And they were insistent that everybody has to be in the office and everybody— they were tracking everything online. There was— and what that said to me, again, because it was a company of mainly employees that were creatives, is you're worried that people are going to be goofing off, not doing what they're supposed to be doing.
Right.
Sometimes some of these folks, they weren't like a 9 to 5. Like, it's not like I'm going to turn on my creative brain. I'm going to work and design all day and then turn it off at the end.
Like, it doesn't work that way.
Yeah, exactly. So, and I think the pandemic opened— they were like, oh, we can't have people who are remote. They have to— if they're not in the office, I don't know what's going on. And I kind of always was just like, this is, this is not right. Now, I left that company before the pandemic, so, um, to go to actually a fully virtual company before it became a thing. So I, I already knew that you, if you found the people who had the right persona, were dedicated, you didn't have to have that concern. Well, you know, the pandemic happens. The company I worked for is still around. I'm still actually friends with them, etc. Now they've got executives who are in different states, not even remotely close to their home office in Pennsylvania. Right? So I think it's, I think it's understanding why a culture is in place. Like, what, what did you Why did you put these things in place?
What were the goals of having everyone in the office?
Exactly. And how can you replicate that on a larger scale? Right. Because it's, it's— and I know there's the whole return to work or return to the office debate that is currently going on. Me personally, I think that's due to a lot of real estate that is owned by large companies. But hey, we can save that debate for another day. But I think if you get down—
You're right.
You're absolutely correct.
Well, thank you. Thank you. Appreciate the agreement there. But I think if you get down to what do you want that culture to be, and then how, how does that, how do those building blocks of that culture live as the organization grows? And some of the early employees may not feel that it's that way anymore. But change is the only constant.
So, and by the way, you're in for a world of change the second you sell the company too. So, you know, understand that basically that the change that the founder is going through, whatever, you know, that founder is going to have to stay for the next 2 or 3 years as an advisor or whatever they're going to do in a capacity. And they're going to watch, they're going to watch— this happened to me— watch your baby be eaten, right, by this other company, private equity, a strategic buyer, whatever, that's going to come in and basically And they're going to tell you that they want to be you. We're a big company with this thing or whatever, but what we really want, we want to be you. We like your culture. We like the way you—
we're buying, we're buying, we're buying you. So we're like, so we change to be like you.
We change ourselves. And guess what?
Nope, nope, it's not.
But you have to sit there and you have to watch what you've built and the culture you've built, especially if you've built a good culture. A culture that people enjoy and they want to be at and the whole thing. It's, it's something that you need to take into account when you're choosing the buyer. And hopefully we're putting you in a place to help you choose, to help you have a choice, right? But the idea is that, you know, you've got that— you have to take that into consideration when you're, when you're making a transition like this, because, you know, you have to decide whether as the, as the founder, this is what you want to do and how you want to— what the integration piece is going to be like.
Mm-hmm.
And, you know, in terms of its effect on your employees and your culture and all that stuff.
And I think you touch on integration, and I think that's a really— and I've gone through that in a number of different scenarios. One early on in my career in corporate America, where I basically had no say on what the integration was going to be. I was told, this is what you're going to be doing. This is how it's going to work. I also understand that corporate America and small and mid-sized businesses are completely completely different environments. However, you still have folks making that decision at the top in a, you know, an act during an acquisition or a merger that they are going to be making decisions that other people are just going to— this is what it is. Um, I've led integrations. I'm very proud to say the, the last one that I completed before I started ThoughtGrow, we had no personnel attrition. And I integrated a team of full-time employees with a team of contract employees.
Hmm.
So that I'm very, very proud of that from that standpoint. The company has since taken off and continued to grow and probably looks nothing like what it was when they had bought the company I was with. But nonetheless, I think there are, there are things that you can do to help that. I also think as a founder and an owner, you need to prepare yourself emotionally and go through all of those stages. And know that, you know, the company that you built was great. You left those employees, et cetera, in a better place than you started with them. And try to remember some of those wins and why you're exiting. Maybe that's for money. Maybe that's because it's just gotten too big and it's not what you want to do anymore. You liked it when it was smaller and you could grow it again. And so when I talk with founders, And they're thinking about what I'll call succession planning loosely, right? Because they're, they're oftentimes, well, eventually. And I'm like, there's like, well, in 10 years. I'm like, it's good you're thinking about it now because it's gonna take a while. But, you know, what the who, what, why, where, and when, right? So if you start to put those, answer those questions, you can start to put together a plan that then you, Jo and John, are like, OK. I know all these reasons behind and what you're trying to get out of it. Now let's make sure that we can get you to that place and find the right buyer. I look at Patagonia. Do you know the story of Patagonia? And the founder is kind of, call him a reluctant founder because money was never his goal.
Right.
And he built this huge company and money was not the end goal for him exiting. And so, you know, there was a trust set up that was— it's a family trust, but then it was more important for him to make sure the employees had a certain work-life structure that they wanted and that the company was doing good and giving back to the causes that were dear to the founder. It's a great example of an exit that is not your typical exit, especially for a company that large, and why answering those questions is so important so that you can plan, that you hopefully have enough time, because we don't— none of us knows how much time we have.
It's legacy, right? I mean, the reality is that there's much more to it. We say it all the time. It's like, look, you don't even know what you can ask for.
Right.
You know, when you're putting together a deal, the whole thing, and you say, hey, look, you know what really matters? I know this sounds crazy, guys, but you know what I really like? I'd like the name to stay on the trucks. You know, and I know, and I want to sit there and when my old age and whatever and watch my trucks go by, you know, whatever, whatever, dude, whatever you want, whatever's going to make you happy, you know, that's what you should be putting yourself in the position to be able to do and to ask for and to get, you know, as a result.
Well, yeah, and like our, our podcast with, um, with Kelly Finnell about ESOPs, right? First of all, we learned a ton about ESOPs, but that's such an interesting way to sell your company. It's like, oh, I'm going to sell it to the employees of the company. Or the Patagonia example. It's like, again, as you point out, Joe, what's important to the founders? Is it important to have a legacy? Clearly, the Patagonia owner didn't care about money and cared more about doing the things, continuing to do the things that the company did while he was there, while she was there, and then moving towards keeping those things in place. And that was the most important part of the deal for them.
So they prioritized that. And we're seeing this right now with a deal that we're working on right now, the whole thing where the founder is very much was a deal breaker was, if you're not going to take these employees on, I'm not going to do the deal.
And, and I think I, I, uh, I really look at that and I'm like, good, say that. Now again, as people who are looking to try to get them the best deal and the best option, sometimes you're not able to maximize—
It's a trade-off.
Yeah, there is, there's, there's, and there's always, but there's always going to be trade-offs.
Right.
And in order for— but, and we're not that founder. We're not in their shoes. We don't know what is really dear to them. But I really, I admire the founders who are able to make that decision and say, this, the, here are my non-negotiables. And then they don't change them. That can happen too. They can say, well, money's not the most important. And then as you start to get into it, you realize, well, I—
That was until I saw the money start going down. Hold on a second. I'm sorry. That stuff I said about money, I meant it when it was $9 million. Now that it's only $6 million, the money matters.
It's a good point, though. And I think, you know, you really have to— you really have to look inwardly from that standpoint. And, Jo, you know that because you've sold a company. You really have to do some soul searching, do some thinking, and prioritize what is most important to you, your family, whomever.
And let me tell you, Jennifer, look, there was nobody around to tell me that, okay? And so, you know, again, what we're trying to do, everybody here, is to give you guys this information because you'd have— otherwise you'd have no idea. I showed up at, you know, we closed the deal. I had 4 partners, first of all, so it was a, you know, it was a bit— it was a— it was kind of a, you know, we were kind of done, so we were all a little bit tired and kind of burned out, and we wanted to be able to, you know, go on to other things and explore what else was out there or whatever we wanted to do. But the thought wasn't really, oh, I'm going to do this next. No one sat me down and said, Joe, by the way, you know, what you got to do is this is going to be a weird thing transition for you because you've been doing this for 10 years. You've had a 10-year life kind of building up to that point before that. And now you're in a situation where you're going to be working for this giant company. You know, I got up, I woke up one day and was told basically to get on a plane and start flying all the way around, all around the country 4 days a week.
Wow.
I was like, wait, what? Oh yeah, no, that's what you got to do now. Now you're managing director at this giant consulting firm that just bought your company. You're now expected to basically go and be on, you know, a team, and you're going to go trout. I was like, wait a second, I didn't have to do that when I was on, right? There was a major cultural shift.
Sure.
A major shift in, in what I— in my own identity, and I was not prepared for that to happen at all. And the wrestling with that and the earnout and waiting for it to be over and all that stuff without really having anybody to sit there and go, hey, this is how you do this. The thought— I was— I had therapy on my own, but it wasn't, you know, it was, but it wasn't related to this. And it was like, I didn't even realize that the processing it was going to take to, you know, to get through that.
And I think that's where you and John bring so much to the table for the clients that you work with.
Right.
You, you, Jo, you've been through it. You, you know what it's going to take, and you can kind of give that inside information as well as helping them to, to realize there's a lot you're going to have to process. And it's not just reading legal documents and figuring out financial statements. There's a lot of, you know, what, what are you willing and not willing to do yourself?
Yeah.
Um, I worked with a company and they, they decided they were going to sell off business unit. And it was kind of the, the, the owner of the company was kind of like, good, done. Like, I don't want anything to do with it. Now, the owner was not actually involved as much in that unit. So it wasn't as big of a deal.
Sure.
But from that standpoint, is it, is it an all-cash deal? And it's just like, you know, hey, we're done. Is it the earnout, which I find to be more common, just because there's oftentimes that consistency, especially in the client, like businesses that have a lot of clients, you want to make sure that the, you know, It doesn't all fall apart and clients are like, oh, change is coming because change is going to happen no matter what. To make that transition smoother, I think that's wise on the buyer's part to have an earnout structure. But, you know, you have to be willing to have a boss now when before you were the boss.
Yeah. Talk about change management, right? You're the boss. You're making all the decisions. You're deciding not to fly around the country. Or you're working on the project. I mean, I remember when my company, the company I was working for, was bought. I was working on so, like, such cool initiatives. And about a month after the close, oh, by the way, all those clients are now going to be serviced out of New York. And I was working in Chicago. I was like, so my, my, basically all my clients are going away and you can't work on anymore? Like, yeah, that's exactly what they told me. Like, oh, great.
This is great.
And, you know, I, and it's hard because, again, decisions are made and You know, you didn't have a say in that decision, right? And that's, that's hard, because previously, you probably would have had some say in where, what you might be working on or what you might be doing. But now, that's it. So it's tough. Any, any sort of integration is difficult. And I think it's, there's communication. Anybody who's gone through change knows that there's a way to communicate. And there's a way not to communicate. And sometimes I feel like there's not enough time spent on managing that message for all the different layers, from leadership, from who was in charge to who is now in charge. And it's obviously there's power plays involved and egos involved.
Personalities and egos and all that stuff too, which is a thing. And again, this is what I mean about the, you know, this is why the, the human being end of this thing is so fascinating to me.
Yeah.
You know, because, and again, any kind of functioning team, I am fascinated by how they work and how they interoperate and the tricks and the tips and the things that way. And again, like you say, putting people in the right seats, right? It's not about the people in general. It's about putting them in the right places. And then, and then the way they interoperate, obviously, with others. And that whole thing is like, that's your, you know, that affects process, that affects your structure, that affects your culture. All those things. And your ability to, as we teach people to look at, you know, 12 different areas basically of their business, you know, and thoroughly examine them. One of them is the, you know, is that we don't talk about enough, frankly, is the kind of the HR or the human being side.
Mm-hmm.
And again, it's not just about, look, the key people that have to go over and all that stuff is part of it. But when you're in a growth situation, The question is, are you getting the most out of your people, right, in the way in which it helps the company the most?
I would agree. And, and what sometimes happens is changes are put in place, new technologies are adopted, etc. And the communication is, this is what we're going to be doing, and these are the benefits the company is going to see. The part that often gets missed in some of those communications are the benefits that the people who are going to be using the new technology or implementing the new process What's the personal benefit to them? And if there isn't any personal benefit, make one up. Because your team needs to feel valued.
Yeah.
They need to feel like you're making decisions that are better for them and the company, especially as you see more and more Gen Z out there that are in, in the, in the workforce. That's— they care about, you know, what's in it for me? Why should this matter to me? And I think a lot of people are focused on the business. The people focused on the business are thinking about the business. But again, it's not just the business; it's the business and the people. And you really need, especially when you're a people-centric— so consulting firms, agencies, anywhere, anything where you have a lot more people, and that's your, that is your product. What your people are doing is the product. You need to really focus on what's important to them.
Yeah, it's like the, you know, you hear about the command and control aspect of like the prior generations and even our generation too. is, this is what's going to happen, and this is how it's going to go. And that, that doesn't work sometimes with, with, with— I don't want to stereotype generations, but, but in this day and age, you can't really have a command-and-control structure. You need to involve people much more and, and create, to your point, benefits for them. If you, if you don't have them already, you need to create those benefits and how this is going to benefit each individual in the organization. And that can be really tough.
It can, because you're not— that's not always, that's not always the reason the process was, or—
Yes.
Being chosen. But if you, but you can often find a reason as to why it will make it better. And then, you know, I look back at some of the agencies and this is another thing, right? So I'm all about efficiency, as I said, but efficiency doesn't mean to me that you're just going to push more work through the, through, through the pipe. Right? I think a lot of people go, oh great, we're efficient, we can do even more. And I, again, I go hearken back to the creative example. Well, why don't you give people time to think and explore and experiment, time to innovate? There's, you'll have the people who are those innovative thinkers, what's next? That time for them should be used to think about things like that.
Yeah.
You know, you've got the people maybe that could be really good leaders and That's a great time for them to do some development. There's the people who want to come in, do a job, and go home. Every company needs them. Yes, you don't want to lose them because if you have a bunch— they always say if you have a bunch of CEOs working for your company, who's really doing the work?
Nothing's getting done.
Right, exactly.
So also, yeah, yeah, I'm sorry, yeah, I interrupted.
Yeah, I was just gonna say— no, no worries. Um, I was just gonna say give those people time back so they're not burned out and they come in fresh the next day, ready to deliver best-in-class service to your clients.
Right.
And when you make the case and somebody goes, oh, I'm like, yeah, you're going to grow. Your clients are going to be happy. Your people are going to be happy. And you can add more people because you have more clients. You don't just get more clients and shove more work on your people because in truth, it doesn't really matter where you're working. Everyone is doing probably more than the one job they were originally hired to do. It's the nature of business. Especially small, small and mid-sized business.
We have discovered that exit planning is the, is actually one thing that potentially involves every single other piece of, you know, business specialty. And so using that as the, as the lens through which we view everything, we feel like people like you, because our model was like this anyway. Right. We already, you know, in our, in, in, at Exeo, we are, this is how we've set this up. A consulting firm that, that owns the client, that runs the engagements, you know, these long-term processes that are going to move people from this valuation to this valuation and this level of sellability to this level of sellability. And we need to bring in specialists to be able to help them along the way, right? Achieve the specific blocking and tackling that's going to be required in order to move the needle.
Absolutely. Because hopefully the, hopefully the, the clients that you're talking to aren't like, hey, I want to sell the business in 6 months. Because usually, I mean, you probably want at least 3 years, um, to make sure you've got all the pieces in place, right? If, if you're going to go for a successful exit, the founder or the CEO, the business owner, their business needs to stand alone without them. And it's, it's hard sometimes for them to put those key people in place. And sometimes I work with a lot of small and mid-sized businesses. They've got maybe one leadership team member in addition to the founder, maybe not. And they're— and they don't want to spend the money to hire a huge leadership team. And I agree, that's not necessarily going to help you. It's where I love to say, why don't you use some fractional folks? Use the fractional folks to get you that critical mass. And, you know, I love to say I'm trying to work myself out of a job. That's exactly what I come in and do. Let me focus on making sure, as either a fractional chief of staff or fractional COO, someone who's helping you get to that critical mass, identifying that persona, so to speak, that it's going to work well with you to then take you to the next level where you can have them full-time. And then hopefully that's another stepping stone to that larger more successful exit that they're probably going for.
Well, that was sort of one of my questions is like, what problems do you prevent or solve as a chief of staff? Like a fractional chief of staff, when you're coming in, what are the core things that you look at when you're coming into a company?
So I like to look at the business as a whole. I'm not going to focus solely on financials or solely focus on operations, although I can do that ops piece of it. It's really the connections and how is the company working together. Well, my clients, what I often see with my clients is there's a disconnect between the founder and the owner and what everybody else is, is doing. There's, there's a lack of connection. You know, everybody's rowing, but not quite in the same direction yet. You've heard that analogy?
Yeah, sure.
Sometimes you don't necessarily even have the right people in the right seats. So it's, it's really, I look at 4 main pillars, call them structure. You know, what do you, do you need? What does your business need to go forward? People and your team. Do you have the right people in the right seats? Do you have process that now is making that team efficient? And then the culture, because what the business owner thinks the culture is or wants it to be is not necessarily what their employees are feeling that it is. One point there that I think is fun, fun to make is I never tell any business owners to apologize for the culture of their company. Your culture is what you want it to be. If people aren't happy with that culture, then you don't have the right people in your company. That, you know, I think, I think you need to, you may need to make those decisions early. But really, it's a connection. It's that Communicating the vision through strategy to initiatives to task-based and making sure that that is a good connection. That's what a chief of staff does, in my opinion.
OK, thank you. That's helpful. So, Jennifer, you are also right. We're talking about this because you're a consultant and you're offering this for a fractional CXO, and for lack of a better term. But you're also a founder.
Yes.
And you've had a couple of different companies. You have been, you've worked in corporate America. You've done, right. You've, you've had your own shingle out in, in, in a couple of different capacities, you know, specifically and things like that. Tell us a little bit about how, about what your, what was your trajectory? What was your kind of journey to getting to where you are now? And, and some of the things, the trials, the tribulations or whatever that, that you, that you, that you experienced along the way.
Well, thanks for asking, first of all, Jo. It's, it's, it's, I call my path the road less traveled. Because I think I mentioned early on, I went from an engineering degree into the world of corporate finance, doing everything from enacting the first Patriot Act changes for a credit card company all the way up to managing the Amazon.com credit card portfolio, and lots of different things in between. Decided to leave corporate America and went to marketing, small marketing consulting firm where I had my own book of business. I mentioned earlier, they asked me to run the sales team. And this is where I started, I kind of started my entrepreneurial journey in a way. And I also started to realize, sometimes you don't realize things about yourself until people kind of tell you when you start to look at things.
Oh, yes.
And it was kind of like, oh, there's a problem. Jennifer can solve that. Jennifer, why don't you take that on? And so my, I realized I love solving problems. And I'm good at it because anytime something comes up, people are like, well, can you figure that out? And yes.
Were you all— I mean, looking back at your life, like, even as a child, like, do you think that that was like a skill that you had, like, from the— like an innate skill?
I think so. And I never— I think solving problems and not shying away from a challenge. So, you know, let's put it this way. I chose my my, my path in engineering, I didn't know what I wanted to do. I, I loved writing. I loved, I loved a lot of different things. And frankly, I was good at a lot of different things. And I'm, I'm not going to apologize for that.
Sure.
My mom comes home one day and she's like, so I was talking to so-and-so's mom and what do you think about engineering? You like science and math. And I said, okay, that sounds great. That's what I'll do. So that's literally how I decided to go into engineering. The same thing with, this is the college I want to go to. Well, where else do you want to apply? No, that's where I want to go. And so I applied early, and I figured out that no other applications were due for another month. So I'd find out if I got in, and I only filled out one college application. So it's, it's kind of, I feel like, in a way, it's like, sounds good. I'll go after that. Okay, that sounds good. I'll go after that. And I chose my path. Or maybe in some cases my path chose me. I'm not really sure, but I never set out to go, I'm gonna have my own business, I am an entrepreneur. Um, truthfully, I think it's funny, I have my own business, but what I like doing is helping other people run their businesses. That's, that's what I love.
That's your business though, right?
That is my business. And, and, you know, my husband and I wanted to start a family, so I left the agency that I was at, um, because I went and I, and I went to work, um, believe it or not, part-time, which was a whole thing for me. I was like, what? How? I have time? And so of course I didn't really, you know, I put in more hours because that's what you're used to, etc. But it gave me the ability to start a family and still be able to be valuable, provide that value. It's one of the things I, I think, um, My— the president of that company, Susan Stipple, for— is— and we built, we built the company from 3 to 4 key people to 15 to 17. All were contractors. We had no full-time people, which was at times an operational nightmare for me because I was doing operations. But at the same time, these were all dedicated people. They were clear about their availability, and our clients loved us.
And it worked.
It did. It worked really well. And, you know, we were virtual before it was a thing. We were all contractors. And then when we sold the company, we sold the company literally February 14th, 2020 was the close date. Wow.
So yeah, you said before the pandemic, you weren't kidding.
I was like, like a week before.
Yeah. Well, it's so funny.
I was at a conference that same week and it was like everyone was coughing and sick and the whole thing.
So.
Yeah, well, if it makes you feel any better, so there's the company we sold to, it's out in Chicago. We, we went out, they came out here, then we went out there at the end of January, right before the first case of we don't know what this is going on. I came back with a dry cough that didn't go away until the beginning of March, but we didn't know. So I was like, was it, was it not? I don't know, we'll never know.
Yep.
But it, but it is funny because everybody's like, ah, and then all of a sudden it's like, oh, everything's shutting down. But what made— and we were doing very well before the pandemic. Then we're starting to talk about integration. The pandemic hits and they're like, listen, everybody has a job. Just keep doing what you're doing. But here's your new profitability model.
And I was like, oh, good. We haven't hidden the business at all. This is just about, yeah, you're right. Here's our new profitability model. Nice.
Exactly. But the good news, they were a wonderful company to work with and work for. And the good news was we were focused on life sciences clients. Life sciences got a lot of investment during the pandemic.
Good point. Yeah.
We did quite well. A year later, the real integration happened. And once I got all of that up and running, as I mentioned, and at this point, all of our work was in PR. So we were really integrating the 2 PR groups. I should say I was integrating the 2 PR groups Because that really was my job at that point. And I loved what I had done. I loved helping grow the company, selling it and then integrating it. And I was like, I can do this for other companies. And so I decided to go out on my own. I started ThoughtGrow, had all these leads, very excited. They all fell through. And so I was just like, oh, okay, see, this is why I wasn't supposed to be an entrepreneur. Because—
Nope. That's exactly what makes you an entrepreneur.
Yeah.
And that is seeing that happen and surviving it.
Well, thank you. And I do, I do think that is probably a commonality for all entrepreneurs out there. Um, however, it just helps me to reformulate what do I really want to do, what do I really want to offer. I dabbled in a little bit of coaching, decided nope, I am a problem solver, I want to consult. I would— doesn't mean I don't offer suggestions or help people along the way, but I I love being in the business and helping figure out those problems so that they become scalable. And that was a good journey for me.
And what did you—
what's your biggest learning along the way? Because it's like, because you've had just a diverse set of experiences through entrepreneurship and big companies and smaller companies. So what do you think you've learned along the way that sort of helps your clients in sort of unique ways?
It's a great question. I've seen a lot, as you mentioned, John. I've seen a lot of things go right, and I've seen a number of things go wrong. And I think the key for me is that you have to make decisions based on the information that you have and not look back and lament that it was the wrong decision or that you should have done something else. Because I think especially during times of uncertainty, which I think we would all agree for small business owners, especially the first 6 months of the year have been very uncertain. You can't be paralyzed. You're not going to make the decisions right 100% of the time. And so that just that trust that you can make a decision and pivot if you need to, I think that's something that I have lived over and over and over again.
Yeah.
And I think that experience and, dare I say, level-headedness in times of uncertainty and ability to dig in and focus is something that can be unique out there from what I've seen.
Yeah, no question. Look, I think that you are, you are, you are hitting on something right now that, again, that, that on both sides of this coin is that What I love about what you do, Jennifer, and where you come from is you are just like these founders, right? You kind of— we talk about this the same way. I mean, John and I, again, we didn't even set up— we didn't even set out to do this podcast like this, you know? And this is the very recent, you know, recent past, right? This was not the thing. We didn't expect to have, you know, 50,000 downloads a month, you know, at episode 44 and all that stuff, right? Like, we had no idea. By the way, thank you for everybody out there for doing that for us. We really appreciate it. We hope we're giving you some kind of value. Obviously, I think we are, which is really fun and awesome. And of course, guests like Jennifer help us do that. But I think that ultimately, you as an entrepreneur, as a founder, you are constantly in that mode of make a decision, try not to second-guess it, make the next decision. Right? Pivot the situation, listen to the feedback, right? You're like in this for the first 18 months at least, right? You are in this notion of, or should be really, Frank, I think should be in this position of trying to learn about yourself, learn about what the thing it is that you are doing and what you are really doing, because it can change as you go and as you get more information and as you go into and meet more people and start to show up to this thing that you're doing every day, you may be coming from it as a product person. You may be coming from it as a technology person. You may be coming at it as, you know, as a, you know, whatever, as someone who likes beach totes, you know, whatever the thing is. And that's not the same as coming from an MBA perspective.
Mm-hmm.
And so many of us fall over backwards into businesses we never thought we'd have or didn't plan to have.
Sure.
Sometimes they grow despite themselves. Sometimes they grow because we just happen to make good decisions or our timing was good or whatever happens. And I think what Jennifer's pointing out to this with her own experience and with her company right now is that you still have control over changing these things wherever you are in the stream right now. And so, and that changing these things is something that, again, is worth the examination. Maybe you don't have to change something. Maybe there's something about your structure or your team or your, or your culture or your, or your, or your, your process that, that doesn't need to change and is really good. But wouldn't you like to find out to make sure that you, so that you know that? And then the next step is, what about the things that I do need to change? Because everybody's got to be, you know, everybody can change something and optimize something. to make their value and salability greater. And with people like Jennifer, you know, out there for you to be able to access, I think it's one of the things that makes certainly what we do easier because we have access to people, because we have access to people like you, and that we can bring people like you to bear for our clients, you know, when we do that as well. So, I mean, Jennifer, thank you so much for being here today. I really, really appreciate your time.
Energy.
How can— Jennifer, how can people get in touch with you if they want to get in touch with you right now? Sure.
So you can connect with me on LinkedIn, Jennifer Cresswell. I'm sure we can put a link in the show notes, maybe, Jo and John, just so people connect there. You can also reach me on my website. It's thoughtgro.com. Talks a little bit about the story, you know, the story, what I do. There's a couple free downloads, I think, that are still out there that could be helpful, especially if you're trying to get yourself a little bit more organized before you make some of those decisions. But yeah, I'd love to have a conversation and find out how I or someone in my network can help.
Awesome. That's so great. Jennifer, thank you so much for being here on the Exit Agent Podcast. We really appreciate your insight, and hopefully we can have you back again. That'd be awesome if we could do that.
I would love to do that. Thank you both for the opportunity. It's been a great conversation.
Thank you so much. Um, John, look, when we— you know, it is what— here's what I love, okay? We are— we have— are growing a network here of people that are like-minded, okay? And what I mean by that is that they are hopefully like-minded like you, the founder out there, okay? Is that they are people that have been through the struggle that you've been through. They have seen it firsthand. They have remedied it. They have problem solved around it.
Right.
They have basically, they have seen it all. And what I love about the, my favorite part about what we do here at ExitEngine is bringing these people into our network to be able to help you all.
Well, yeah. And the last point that Jennifer made, I thought resonated with me is, you know, what has she learned, right? It's, you have to make a decision as the founder of a company. Don't let the fact that you don't have what you think is not all the data in order to make a decision. You're the founder. You're— the buck stops with you. You need to make a decision to move forward. And yeah, you hope it's not one of those, those one-way doors that are described, or that you can pivot later. But you need to make decisions as the founder of the company to move forward and to drive your team forward and to demonstrate your leadership. That's what the founder does. No tough decisions make it all the way up to the founder. All those things are done earlier. You need to move forward.
Exactly right. And the way that you— yeah, sorry, Jen.
I was just gonna say, I like to say indecision is still a decision. You're just giving someone else control.
I like that.
That's really good. That's exactly right. And we are all about at Exit Engine, obviously, controlling your own destiny and controlling your business destiny. So, guys, everybody, thank you so much. Jennifer, thank you again so much for being here. Really appreciate it. You guys are going to see more Jennifer in the in the in the in the next couple next few months, I promise. And maybe she doesn't even know that, but she will. But you will. In any case, we really appreciate you joining here on on on the on the Exit Engine podcast. I'm Joe Stapleton. That's John Kniff. Again, you can if you've got a question about where you are right now, about what you should be doing and what you should be looking, we are available for you whenever you like. Okay, you can email us at info a i n f o at myexitengine.com. You can email me directly, jo@myexitengine.com, or john@myexitengine.com. Find us on LinkedIn. Joe Stapleton, again, is Joe without the E. Find us on LinkedIn, send us a direct message, send us a note. You've got a question, we've got an answer. We're glad to help you. If there's somebody that's been on the show and you guys want to, want to, you know, to get in touch with them or whatever, that's fine too. Feel free to reach out. We can help you with Jennifer's contact information or anybody else we've had on the podcast here as well. Again, John, thank you so much. Jennifer, thank you so much. Everybody have a great day and let's— here's to exit success. Thanks, Joe.
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