Podcast
Business growth often introduces new challenges: hiring the right people, navigating expansion opportunities, and adapting to unexpected market shifts. So how can leaders make informed decisions at each stage without losing momentum?
According to seasoned operator and strategic advisor Rob Stepen, it starts with understanding that every stage of growth demands intentional choices. He stresses building a people-first organization by hiring adaptable, customer-focused individuals and addressing misalignment quickly when people are in roles that aren’t the right fit. Rob also recommends aligning acquisitions and partnerships with long-term strategy rather than short-term gains, while staying focused on what you can control. Disciplined decision-making and strong team alignment sustain growth over time.
In this episode of Growth + Exit, Heather Bennett talks with Rob Stepen, Certified Business Performance Advisor at Insperity, about scaling and exiting a business. Rob explains how to hire and structure teams during rapid growth, evaluate acquisitions and mergers strategically, and navigate the challenges and lessons learned from selling a company.
This episode is brought to you by Newport LLC, a national business advisory firm.
Newport is a team of over 50 seasoned C-suite executives who have founded, built, bought, and sold businesses. We help CEOs of privately held companies achieve exceptional value quickly and with less risk.
We use our proprietary Value Acceleration Program — a set of research-based tools and methodologies — to help growth-stage businesses build and sustain value.
To work with us, visit https://newportllc.com/.
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00:06 Intro:
Welcome to the Growth + Exit podcast, where owners of privately held middle market companies talk about founding, scaling, and exhibiting their businesses successfully. Learn how to maximize and monetize your business on your own terms. Let’s get started.
00:30 Heather Bennett:
Hello, I’m Heather Bennett, your host for the Growth + Exit podcast, featuring middle market owners and experts talking about founding, growing, scaling and exiting their businesses on their own terms. Past guests include Whitney Opperman, general manager of Opperman and Sons. Matt Vuckov, co-founder and CEO of TalentCraft, and Kelly Schrad, founder and chairman of DataVizion. This episode is brought to you by Newport LLC, a team of seasoned executives who help CEOs of privately held companies grow, de-risk, scale, and exit their businesses successfully. Newport LLC is a winner of the prestigious Inc. Magazine 2025 Power Partner Award, a list of elite B2B companies from across the globe.
To see the entire list, visit inc.com/power-partner-awards. To learn more about Newport, visit us at Newportllc.com or find us, of course, on LinkedIn. Before introducing today’s guest, I would like to thank the many colleagues Rob and I have in common for introducing us to many to list. Today’s guest is Rob Stepen.
Rob is a seasoned operator and strategic advisor known for helping founders turn early traction into disciplined, scalable growth. With deep experience across many different fields and expertise, Rob has guided multiple companies through the critical inflection points that define the founder journey, building systems, strengthening teams, and creating the operational clarity that fuels sustainable growth. Today, he works closely with business owners and investors through his job with Insperity to help handle all say, a lot of challenges in the business world. In addition, Rob has a band called his band is called The Generations, and they perform in the Chicagoland area. And I had the pleasure of getting to sing with them a few times.
So Rob, welcome to the show.
02:34 Rob Stepen:
It’s such a pleasure to be here, Heather. And sorry about the lights. That happens every so often when there’s no movement, so I apologize.
02:44 Heather Bennett:
Oh, smart tech buildings are where it’s at. I love it, I love it. So let’s get right into you as a founder, because I described a lot of the work that you’re doing right now. But I want to hear your founder’s story. How did that get started?
03:01 Rob Stepen:
So my my journey started actually in corporate America. And I worked for the Quaker Oats Company, which became Pepsi. And I started like ground level and worked my way to corporate managing about $450 million worth of Quaker Oats instant oatmeal business on a cross-functional team. I was a national trade marketing manager for Quaker. Then I went to IRI Information resources is is a associate director there calling on ConAgra, Alberto-culver and Keebler.
After that went to Advo Direct Mail Marketing as a director, calling on SuperValu, JCPenney, and Caribou Coffee. Then I decided I had that entrepreneurial itch and I decided to open up my own business. And I, you know, grew it from ground level to, I think at the height we had 22 people working for for us. So my cousin and I started it. It was in janitorial, sanitation and maintenance supplies, focusing on food safety, sanitation.
So the verticals that we competed in were things like retail, grocery. We also had healthcare, hospitality, and education. Those were the four verticals that were predominant, and we worked with people like Whole Foods. We had, you know, regional contracts with those guys. SuperValu was another big client, you know, and a bunch of players in the healthcare space.
So I was so fortunate to get experience through the whole M&A journey, if you would. I, I, you know, opened this up with my cousin. We started to scale the business as part of the growth plan of scaling. We acquired a firm. We also had some channel partnerships and then we merged with another firm and.
And then finally, after 22 years of being in that space, I wound up selling. And then I went back into corporate America working for Ifma, the International Food Service Manufacturers Association, as the marketing director, focusing on digital marketing, which is really hot. Now you know that digital is where it’s at. And then after that, I wound up in supply chain, and that’s where I found Insperity because I was a client of Insperity before coming to Insperity. So I’ve really come full circle to be a business performance advisor for my clients.
05:36 Heather Bennett:
Excellent. And I love hearing that story. And I know we’ve been very lucky on the show to have a number of excellent, we’ll say, marketing field founders, you know, Stephen Brent-May and Hami Arrington, Mark Bealin, Tim Padgett, and of course, Scott Markman. So really, really exceptional marketing leaders. So it’s good to hear about your experience.
So when you were building that, that company and you said you went up to like 22 and I know you’re, you know, Insperity is such a people focused business. What was it like determining when and how to hire and bring on new people for that business?
06:22 Rob Stepen:
That is a wonderful question. So as we were, we were growing and we would sign contracts. We would have to have people, you know, to, to fulfill certain roles and responsibilities within those contracts. So as an example, I remember, remember when nine over 11 hit, you know, everybody has that memory. Like, where were you when that hit?
What what happened back then is I had to pivot Heather because, you know, all of a sudden businesses were were going down and some of them were tanking and the sky is falling and you didn’t know there was so much uncertainty in the world. And so I had this idea. I said, you know, in, in food safety, sanitation, what’s really important is, is getting trained. So I wound up training like 1000 Whole Foods employees, myself and my team. And, and so I thought, wouldn’t it be cool to have a just in time delivery system and training and then servicing the stores of whether it’s Whole Foods or SuperValu or some, you know, some other grocery stores or restaurants and having like an account service manager, I created this brand new position account service manager that would have a truck and have product in the truck and have tools in the truck and then go around to all the sections, let’s say at Whole Foods, it’s prepared foods and meat and seafood and produce and cheese and all these different, you know, departments and, and make sure all the equipment, dispensing equipment for the chemicals work properly.
There was, you know, so being proactive instead of reacting to it, you know, Saturday night, you know, the sky is falling. So we didn’t have to have those type of situations. But also they, they do a just in time replenishment, you know, with, with all the products that they purchase from us. And then that person would also do training. So maybe there’s some new hires at Whole Foods that or SuperValu that needed training.
And so this person was like a, you know, a, a jack or Jill of all trades. And I had to go hire for that, you know, so I had to staff up because all of a sudden we’re, we’re in 11 different states. We go from being in Chicagoland area, maybe into Wisconsin to to 11 different states in the whole Midwest. And I had a staff up. And that was an example to your question of, hey, how did you know when to staff up?
Well, I knew because I came up with this model and I didn’t know how it would work. But it was it was very successful.
09:03 Heather Bennett:
And, and when you were looking for that jack of all trades, that person who can really do a lot think on their feet, be able to say what, when you were interviewing them, what were you looking for in their responses or on their resume that told you they’d be able to handle that agile and flexible of a position?
09:21 Rob Stepen:
So the first thing they had to be a people person because, you know, they were the face of my company. And, and if you didn’t have the right person, if you had somebody that didn’t have those type of skills that wouldn’t fly because I’d be getting calls left, right and center saying, who is this person? And so being a people person was number one, being being somebody that was flexible because you just never knew what kind of issues that were, you know, at the store level or at the account level. And then you had to pivot, you know, you had to take care of things. If their dishwasher didn’t work, you had to know how to fix the dishwasher.
And so there’s all these different things. And then mechanical, they, they definitely had to have that mechanical background. They had to have some, some sense of how they would train people. So and, and they didn’t have to have that all coming into my company. I, I actually trained a lot of them.
And, and I did, you know, like, like real training at the site. So, you know, that as that became more ingrained in their head, it was like second nature to them. And then they had to know how to use. I think we had like iPads at that time. So they had to or something like that.
They had to, you know, have some technical expertise as well. And those were some of the critical components of how a a successful account service manager or we call them asms would be.
10:59 Heather Bennett:
Then that’s that’s cool. That is really cool. So, you know, you, you, you’re growing the company and, and you don’t just grow the company by people talk about your endeavors into the world of acquisition.
11:17 Rob Stepen:
Sure, sure. So, you know, when you have a growth plan, you have to think about, am I going to grow the company organically? You know, you know, how is that going to work? Are you going to do it through acquisition? Because when we acquired this firm, when we were interviewing different firms throughout, you know, I’d say the first probably 5 to 7 years of our existence.
They had to check some boxes, and even firms wanted to merge with us at that time. And that happened later on in, in the the life cycle of the business. So when I thought about acquisitions, you know, what is their culture like? You know, what, what, you know, the people coming over to my company, how are they going to align properly? And that was like really big for me culture.
And now it is to for Insperity, you know, that’s like another biggie for us. But then also, you know, I, I had a, I had to dive into the numbers. We, you know, I had, I actually had a third party gentleman that would help me for all the analytics and make sure that, you know, number one, it’s, it met the needs, you know, you know, ground level, but where’s that going to be down the road. You know, like do some projections 3 to 5 years out. How is that going to look?
You know, and how is it going to add, you know, to my, you know, my company’s financials? What is the EBITDA going to look like? You know, down the road and obviously as growing the top line and you know, this, you know, from from your business, is it, you know, what, what kind of efficiencies are you going to get? Because, you know, now your, your one plus one equals three type of thing where, you know, you can get some buying power to. And now we’re at a different level to buy at.
And so those are things that we’re really important at that time. And then, you know, what kind of equipment do you have? Do you have any trucks? Do you have stuff that will help our warehouse? And what type of lines of products do your customers have versus our customers.
And are there any lines of products that we can take on that will enhance our portfolio and grow our portfolio? And then people would say, oh my God, that’s pretty cool. You have, you know, this chemical or you have this tissue, you know, you know, program. So those are the kind of things that we looked at when we were interviewing. And then finally when we made the acquisition.
14:01 Heather Bennett:
All right. So then we’ve talked about acquisition. How about merger and exit? So what happened with the company?
14:11 Rob Stepen:
So the merger the the thought was we were not strong with my company in healthcare. This company was very strong in healthcare. And we merged the companies together. So we were really strong in retail grocery. We were really strong in hospitality as well as education.
So that added a component that we did not have. And so there was over, I think it was over like a couple hundred accounts. At one point we were over a thousand accounts as a company. And so that really helped and get us into different, different verticals. And then they were in a few other verticals too, but that was the major one.
And then there, there were two partners that came on with me. So there were three partners total, and then they brought on a staff of people as well. Now what happened was we didn’t really need this huge staff, you know, so we can consolidate that, you know, moving forward. And then we, you know, obviously from the acquisition and then the merger, there were more sales people because you always want like, who’s going to have a book of business? And what are you going to do with that book of business?
So those were all factors in both the acquisition and the merger. And so when when we got to a point where I would say in 2016, there was a lot of changes that were going on in the state of Illinois, the state was broke. You know, they weren’t paying the health care. And so cash is king. And and if my clients are getting paid and we’re not getting paid, you know, for a period of time, not not forever, but, you know, you, you’d want people to pay you within your terms.
However, if Illinois is not paying the, the, these facilities and these entities that that really put a crimp on things. So knowing that, knowing that everybody wanted to get into janitorial supplies, all these big box stores. And so that was hurting margin. And then Whole Foods got acquired. That was a big client of ours.
So that they, they got acquired by Amazon back then. And so then we started looking about, you know, okay, let’s start the whole selling process. And that’s how that whole those three components really had us look at that.
16:46 Heather Bennett:
Yeah. So those are some major shifts in the marketplace. Yeah for sure. And tell me about that process because most people only go through the sale of a company once in their lives. So, so tell me about like, how did you start it?
What did you learn? What surprised you?
17:09 Rob Stepen:
Well, I think, I think the, the surprise was that I thought there’d be more people that were looking. We did interview a few people and, and everybody, it was just tragic because they wanted to lowball things and that that wasn’t a nice experience. You know, when somebody just wanted to pay you, like, you know, bottom line price, we wound up getting a decent sale, you know, from our sale. But as we were going through the process of, of interviewing these different firms, you know, some of them were really good. Some of them I could have seen myself working in, you know, a long time because they had great culture, they had great people that worked for them, great leadership.
And but, you know, who wants to if they were going to lowball me, then who’s to say what would happen down the road? You know, Heather. And that wouldn’t have been a fun experience. And then I had some family members that wanted to interview me. And so I thought that was more of a conflict.
I didn’t want to upset the apple cart going with some of the family members organizations, and we wound up selling to a gentleman that actually was in health care and he had he had owned health care facilities. And so the supply business was like adjacent and really helped him, you know, so he didn’t have to go find vendors. And, and he actually saved his margin on that as well.
18:44 Heather Bennett:
Yeah, certainly acquiring in order to increase your vertical, never a bad thing, never a bad thing with controlling costs. Very interesting. What do you wish? You know, with Newport, a lot of the founders I work with and my partners work with, when we start talking about eventual exit, there’s a lot of information they just don’t know. Like I said, when you only go through this once in your life, what’s the likelihood you’re going to understand the process ahead of time?
What do you wish you would have known in order to be more capital ready for that process?
19:22 Rob Stepen:
You’re you’re going to love this answer. I wish I was an inspired client back then, because what Insperity does for those types of organizations, we actually get people moving. You know, like to the top line. So if somebody really cares and values their employees and we get involved with them in multiple ways, that’s going to help grow your business and that’s going to get you the best bang for your buck when you’re ready to sell. So you know, when, when you’re looking through different inflection points in that journey, so to speak, if you are ready to sell, which we were at that time, and Insperity got our people to the next level.
So as an example, maybe they could have trained our sales people to be more effective and efficient and get more accounts and be more hunters out there to drive the top line, we would have got more money, you know, at the very end. And so I wish and then, you know, Insperity would have that HR infrastructure. So I wouldn’t need certain people that I think I was overstaffed in some of the areas. And so Insperity could have helped that as well. And, and it’s not a plug for Insperity.
It’s actually true because when I was a client of Insperity, I saw how efficient, you know, that the organization was and how we grew. We were 16 employees. We were like $72 million. And before Insperity and once Insperity came after two and a half years, we grew to a little over 100 million. So like $28 million, you know, pop in, you know, to the top line really helped positive drop through to the bottom line.
And so, you know, comparing and contrasting, you know, I didn’t know about Insperity back then. So, and, you know, it was funny because when I first came to Insperity, one of my colleagues, you know, was talking to me and he said that, you know, where did you work? And, you know, I said, well, I wish I would have known Insperity and, and, and the manager looked at my colleague said, why weren’t you calling on Rob way back then? So it was like really funny that had he had called him, I may never have been an inspiration in spirit. He probably would have helped my company.
21:46 Heather Bennett:
Yeah, and I love that you mentioned that because there’s so many specific levers, you know, there’s like 4 or 5 very specific levers that you can push and pull in order to generate growth. And one of those is exactly what Insperity does, which is really focus on that people component. And so that’s such a great example. Okay, so you’ve exited the business. Yes.
What what surprised you afterward? Because I’ve been hearing a lot of like fun conversations about you’re the business owner, you’ve got this business, it’s running great. You survive the due diligence and the process of going through M&A. You know, what was that 1 or 2 years afterward like?
22:28 Rob Stepen:
Well, I was between successes and the surprise for me, Heather was, okay, what’s my what’s the next chapter in my life? And it was surprising that I thought I could just pick up right away, you know, get somebody to, you know, hire me or, you know, and I, I thought about, hey, what’s the next widget that I want to launch? And, and so what I did was I kind of did parallel paths. I had my own consulting company, Ross Consulting. And so I would actually consult on marketing for businesses.
And then Ross morphed into the whole music, you know, scene. And the band is through that entity. But surprising. I, I, it was just so difficult for me to get the right job. And then I finally landed at Ifma.
And Ifma was a great opportunity, a great springboard for me because it got me back into doing marketing on a day to day basis and doing digital marketing and working with all these different companies. They were not for profit. They, they, you know, had members from big, you know, CPG companies, which was that was my, my starting point with the Quaker Oats company. So I felt really good about that. But prior to that, the surprise was, okay, next, next, next.
You know, I had all these interviews and it was it was great. And I had recruiters call me and, and here’s, here’s an interesting story about connectivity that I think maybe your, you know, your clients and your audience would like to hear about. I’m a firm believer in connecting the dots. So during that journey of, you know, between successes, I had an interview and it was a nice interview, nothing special. I was downtown and I said to myself, you know, I’ve never really seen the American Marketing Association.
I’ve been a member of the American Marketing Association. I never saw it. So I called them up, said, hey, downtown for an interview. You know, can I just tour your facility? Yeah, come on down.
I’ll take you on a tour. So I get there, and the person that was supposed to take me on a tour left for an early lunch. And there’s this gentleman at the at the front desk, and I’m telling him, yeah, I want to take a tour. I’ve never seen the place. Been a member all these years.
He said, I’ll take you on a tour. Oh, great. He takes me on a tour like he shows me all these different rooms. They have different themes in the different rooms, like Mad Men had a had had their own room and it was really cool. And so we started talking and he was asking me about my background and I said, oh yeah, I was a Quaker.
He goes, oh, do you know so and so? I said, yeah. She ran Gatorade. And, and so we, we had some commonalities there. And at the end of the tour, you know, we’re talking.
He said, do you ever volunteer here. So I’d like to. Yeah. I don’t know anybody, you know at the at the organization. And so I said, by the way, what do you do?
And he say, I’m the CEO. I’m like, oh, you’re the CEO of the American Marketing Association for Chicago. He goes, no, I’m the CEO of all the American Marketing Associations. And my jaw dropped and we start talking. He said, I’ll tell you what, you start volunteering here and coming to more events, and I will connect you with somebody, and that’s going to be a recruiter.
And he did. He connected me with a recruiter, and that recruiter got me the job at Ifma. So you just never know what will happen. And now that was just, you know, top of mind. Hey, I’m down here interviewing with this other company and just, just making those connecting the dots, you know, types of situations really helped me and, and, and connecting the dots have always been, whether it’s running my own company, whether it’s getting clients, whether it’s helping others out by helping them connect the dots.
You’ve, you’ve been at my events and you see how I can connect people together. That’s, that’s really important to me to pay it forward.
26:48 Heather Bennett:
Absolutely. Okay. So speaking of paying it forward, who are your mentors and what are the what’s the best advice you’ve ever received from a mentor?
27:00 Rob Stepen:
Excellent question. So I’ve, I’ve had multiple mentors throughout my whole life. When I started with the Quaker Oats Company, Jim Koy, you know, was one of my big mentors at Quaker, and he would always talk to me about really getting to know people, getting, you know, being curious. That was his big thing, being curious. And I still take that on, you know, today as, as, hey, I, you know, whenever I talk to somebody, I want to know about their business.
I want to know how they started their business. I want to know, you know, what’s important to them and how I could help them out. So that was one mentor at Quaker. The second mentor was Dave Berry. Dave Berry was the president of, I believe it was the foods Division.
And he, he, he often told me, he said, Rob, you got to work. You know, you can’t be like working at all these different projects. You got to focus, focus on two, maybe three things, but focus on these two projects and do it really well. And I still remember that today. And so those were those were people at Quaker.
But I’ve had a series of mentors that, you know, have taken me under their wings that that have coached me, you know, even even here at Insperity, my current regional manager, she always takes me under her wing, her wing, Maureen, she, she’s just incredible. Maureen Logan and she teaches me things that I never would have learned before. And so I appreciate that. But I’ll tell you a story about somebody that made a very big impact on me early on in my career. And that was Payne Stewart Payne was this champion golfer, and tragic thing happened to him later on.
But I had an opportunity to do an event with the Quaker Oats Company, the NFL, the PGA, where we took our clients to a golf course, and Payne and his team put on a clinic, and then we got a chance to go off with Payne and our clients and all that stuff. So I remember golfing with him at one of the holes, and I pulled him aside and said, Payne, you know, my buddy Scott’s doing better than me on this course. And and he said, Rob, he’s not doing better than you. He said, he has nothing to do with you. I said, yeah, but he’s looking at how well he’s doing.
He said, he said, that’s all on you. You get a chance to control what club to use, what ball to use the the conditions of the course, the conditions, the weather conditions. You need to focus on yourself and not worrying about other people. And he said, you take this lesson in golf and you apply it to business and don’t care about anybody else and how they’re doing and how well they’re doing. You just focus on yourself and control what you can control.
And that I that has has, you know, gone with me my whole career. Whether owning a business, whether working for somebody I, you know, I, I applaud people and congratulate them. But, you know, I don’t, I don’t get that, you know, in my headspace, you know, I don’t, I. Good for them. I’m just worrying about myself and that that probably is one of the best advice that I’ve ever received from somebody.
30:41 Heather Bennett:
That’s terrific advice. And yes, focus is, is absolutely key to getting things done. I have one last question. But before I ask it, I want to make sure that our audience knows that you can be reached through LinkedIn. Rob Stepen And then last question, what is a hard lesson you learned while starting and growing your business that you wish you could share with future CEOs and business owners to help them more successfully grow their businesses.
31:14 Rob Stepen:
It’s all about the people. And if you get the right people and the right team together, then you can grow at a greater clip than if you have the wrong people. And if you let the people stay longer, which I did because I became too loyal. I believe that that, you know, they weren’t the right fit. And, you know, I, for whatever reason, I was focused on something else.
And I really should have been focused more on the people at that time. And it was a, it was a learning it was like a wake up call for me, Heather, that once I got the right team in place, we were humming like a well-oiled machine. And it took a while to, to get there. But once we did, we, it was exponential, you know, in terms of our growth. And I would just say, make sure that that you treat them well.
Because if you don’t treat them well, they’re going to look somewhere else. So you want to have a strategy to attract and retain the talent that you have. And that was the my biggest moment that and you know, when I said earlier, hey, I wish I would have had Insperity Insperity is all over that, you know, attract and retaining talent. And so I, you know, that was a big thing for me. And if I had to do it over again, I would do things 100% different.
Just focus on the people and they would help me get to the next level.
32:44 Heather Bennett:
Absolutely, absolutely. I’ve been talking with Rob Stepen, founder guitarist, with his band The Generations, and a leader and an Insperity. Rob, thank you so much for sharing your story and your experiences.
32:59 Rob Stepen:
Thank you so much for having me. What an honor. And you know, Newport is an awesome company, and if anybody wants to go through that, they know the growth and the selling of their business or the whole M&A journey. I recommend you guys, you know, 100% okay.
33:18 Heather Bennett:
He is not being paid for this, but we are delighted to have you as a partner. Of course. Thank you, thank you.
33:31 Outro:
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