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Scott Barstow – Keys to High Performing Product Teams – Ep.202

Scott has founded and led tech companies and teams throughout his career. He now supports the Pacific Lake portfolio as an operating partner focused on building great software product and engineering orgs.
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Episode Description

Ep.202: Alex (@aebridgeman) is joined by Scott Barstow (@ScottBarstow).

My guest today is Scott Barstow. Scott has founded and led tech companies and teams throughout his career. He now supports the Pacific Lake portfolio as an operating partner focused on building great software product and engineering orgs. I’ve had the pleasure of getting to know Scott through my Chief of Staff role with HW Media and Pacific Lake’s executive leadership program, and I think highly of his perspective on software and team construction.

Scott has spent years thinking about what makes high-performing product orgs work, and in this episode, we dive into key characteristics of high performance and how software CEOs can implement them in their product teams. We talk about key fundamentals like culture, communication, ICP, to more complex topics like Conway’s law, the role of leadership, and recruiting tactics and strategies.

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Clips From This Episode

How to Effectively Communicate Across an Organization

Building Trust in an Organization

Ravix Group — Ravix Group is the leading outsourced accounting, fractional CFO, advisory & orderly wind down, and HR consulting firm in Silicon Valley. Whether you are a startup, a mid-sized business, are ready to go public, or are a nonprofit, when it comes to finance, accounting and HR, Ravix will prepare you for the journey ahead. To learn more, please visit their website at https://ravixgroup.com/

Hood & Strong, LLP — Hood & Strong is a CPA firm with a long history of working with search funds and private equity firms on diligence, assurance, tax services, and more. Hood & Strong is highly skilled in working with search funds, providing quality of earnings and due diligence services during the search, along with assurance and tax services post-acquisition. They offer a unique way to approach acquisition diligence and manage costs effectively. To learn more about how Hood & Strong can help your search, acquisition, and beyond, please email one of their partners Jerry Zhou at [email protected]

Oberle Risk Strategies– Oberle is the leading specialty insurance brokerage catering to search funds and the broader ETA community, providing complimentary due diligence assessments of the target company’s commercial insurance and employee benefits programs. Over the past decade, August Felker and his team have engaged with hundreds of searchers to provide due diligence and ultimately place the most competitive insurance program at closing. Given August’s experience as a searcher himself, he and his team understand all that goes into buying a business and pride themselves on making the insurance portion of closing seamless and hassle-free.

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(00:00:00) – Intro

(00:04:14) – Framing the goals of a Product org and key roles

(00:07:53) – Defining Product Software companies and key differences between product and engineering

(00:14:16) – Who determines the priorities of features and creates a product roadmap?

(00:16:48) – How to effectively communicate across an organization

(00:23:04) – How the CEO’s role plays in prioritization

(00:25:43) – Building trust in an organization

(00:33:19) – Benchmarks for timing from idea to shipping

(00:39:15) – How $5-$10m ARR product orgs scale

(00:47:34) – Keeping teams independent and autonomous

(00:56:41) – Recruiting

(01:07:18) – Final thoughts

Alex Bridgeman:   You seem to have a very strong intellectual curiosity. Where do you think that comes from?

Gary Walter: Failing at different things and learning as you go along the way and taking jobs that you don’t know what you’re necessarily doing when they come across your way, like being an entrepreneur and growing a business, having not done it before, you start to learn how to do things, you move into- To be successful, you have to move into a very proactive mindset. Being proactive means looking at what could possibly happen before and trying to think of the outcomes and think of the good and the bad along the way and then researching the things that people have done before. And I think that’s really what it comes down to is the more I wanted to do better and I wanted to step up and change who I was, it required me to find out what that is before you can do it. Because you just- a lot of people get stuck in a process, just get stuck in a daily grind and daily process where they don’t know what to do next. It’s not that they don’t want to, it’s not that they don’t want to grow, it’s just- and they’re trying their hardest, but they don’t know how to do things differently because they haven’t been exposed to it. And so finding ways to be exposed to new and different companies, ideas, processes, management ideas, data flows, whatever it might be, you just have to accept that your way is probably not the only way, probably not the best way either and just kind of keep continuing to look for what else is out there and what’s better and then take the good from the bad and choose what works for you.

Alex Bridgeman:  How did you do that as CEO of Infutor? Was there a certain type of research or dedicated time you had just to like see what else was out there, what other companies were doing, what peers of yours were trying?

Gary Walter:  It’s hard to define, to say like a dedicated time. I would say that was the majority. So as the company grew, and especially as we brought on a formal investor from Norwest Venture Partners and a growth equity partner, I wasn’t a salesperson anymore. Even though I had the CEO title, most of what I was doing before was selling and you really tried to get out of that and work and think about what is working on the business. So, as I got more comfortable and handed over and took all the hats off and started to hand them down to the team, it did develop more time for me to go out and think what is next, where do we go, what do we do, how do we make this place better. And I think what really pushed me a lot in wanting to do it was I was fortunate enough to hire really good people to support me and around me that were a lot smarter than me, a lot more experienced than I was. And that came from a board level, from independent board members to the operating people within the business, from my CRO and from our CTO and our CMO, and we had a really great leadership team all the way around. And they were constantly talking about things that I didn’t know upfront. And that is hard to admit sometimes. But once they get comfortable, just saying, hey, I trust you, and I get it, let’s go for it, it sounds very fair, I developed a really good cadence and process to be able to trust and verify, to make sure that I did really truly believe and agree with what they were doing.

Alex Bridgeman:  Can you give a high-level summary of what Infutor does? And of course, you worked in business before becoming CEO. So, what was that journey like too?

Gary Walter:  Yeah, so Infutor itself is no longer in existence as it is. We sold the company to Verisk in Jersey City, a large publicly traded insurance data processing platform, and it’s a really incredible business in the way of how they built and how they grow and how it’s grown and their penetration within the insurance vertical and how they command that space. And so, we sold in February of 2022. And from there, it evolved to become Verisk Marketing Services. It was very exciting to me to see a large institution like that take our family business that we evolved into an institutionally owned business but really focused on having a family-based culture in that it was my baby, it was our baby. And to now watch that turn into something that will truly go on forever that’s looking at more of, instead of a five year lifecycle with a private equity investor, to a 25 year lifecycle and where does it go and how does this thing evolve to really dynamically change the insurance marketing space, that is very exciting for me to have that thing go on forever. Because often businesses, as they are, have to go through phases. They have to change, they have to adapt, they have to- in order to keep growing. And we were at an inflection point. We’re five years into a private equity hold period. That’s generally about the timeline where investors want to start thinking about how they’re going to get their returns on a business. We as a team were ready as well. And my family was ready as well. So, it was a good long run, but it was our time to come to the end with this business. And we did what we thought was the best we could do with it and still had multiple growth opportunities looking forward, which is very exciting. But it is hard to hand over the keys to the kingdom. So don’t underestimate that as well. Infutor itself, the journey, my dad started the company in 2004 after working in business data since the 70s. It was sort of a pivot after he had sold his last company International Business Lists to Targus Info to kind of move into the consumer data and consumer identity management world. There’s a bigger marketplace, a different type of marketplace that he had been in before but very much the same principles as business data. But the consumer data had a lot bigger universe to work for, and our talents, our family talents were processing data, being able to create linkages, find patterns, find the ability to create products from intangible basically phone books, electronic phone books, and turn them into something that can change the way a market works or a transaction workflow does things, change how a banking system does things, or a marketing application can target new individuals or verify inbound consumers coming into their platforms and those types of things. It’s very exciting to really step back and think about what that looks like when you think about everybody gets a phone book. Everybody knows what it is. How do I really change the marketplace with that information and do it in a privacy centric way, in a privacy focused way, where it’s a sensitive topic to a lot of people. So, it was very exciting. I joined the company with my dad. I was the fifth or sixth employee, I think, when I started in 2007. I traveled with him, learned data. I didn’t really even know what the company did when we started. I just knew I didn’t- I needed to take a leap of faith and become an entrepreneur, whatever that meant. And that’s another topic that I think a lot about – it’s like how do people know when to take the leap? I truly did not know what data was when I started with my dad. I never really knew what he did. And it’s a very hard concept to just say, hey, we just do data. What does that mean? That doesn’t mean anything. So, I started as a fifth or sixth employee. We had a great initial growth period. My dad had sold a couple million dollars of business, he had great cash flow coming in, really great margins, a really great buffer for success. So, I said, well, now’s my time to take a leap of faith. I guess, if it doesn’t work out, I don’t know what I’ll do. I’ll go back to- I was a teacher before that. I can go back and be a teacher or something like that, fall back to that. But I think we can make this work. And I think it’s interesting to me. So, I traveled with him, learned the business, learned the marketplace, learned the customers, just hands on experience. I mean, from making marketing material to cleaning the office to finding new offices to everything that had to be done, there was no one else to do it, so I did it, which was great. I really learned hands on the bones of the business and how it worked, which fast forward in 2012, my dad was diagnosed with kidney cancer. He died four months later. I was the Walter last name there, so I got the CEO job, not qualified or unqualified. I don’t really know if I was or not. But I knew that I had my time; it was my time to shine and my time to take care of this baby that we had started to cultivate and to start to evolve that into the what I would call second iteration of the business, the first iteration being what my dad’s period was, the second now my period as the CEO. So, I shut off some of his pet projects that weren’t really going to get any traction or any growth. They were just things that he had wanted to do and he liked. But the company was not aligned around growing these things or necessarily doing anything with them. And so even the best pieces of software, pieces of data, or whatever they are, if there’s no one to sell them, and they just sit on the shelf, then it doesn’t matter if they’re good or not, no one ever knows. And so those were just things that we needed. They were great platforms for markets that I didn’t really know, I didn’t have passionate about, and quite honestly, it was the right thing for us to do to just anchor down and focus in on the core of the business, which was really what our foundation was, who truly we could serve well, what data we knew worked well, focus on growing and scaling that out because, quite honestly, like I still had to figure out what I needed to do there. And I needed to figure out what the team was, where the people were, we had to make an org chart. We didn’t have any of that stuff. So, there was a lot of just sort of taking a step backwards in order to take more steps forward. So, we did a great job. 2012 to 2015, I think we went from roughly 9 million in revenue to 20 million in revenue. In September of 2016, I worked with Norwest Venture Partners to bring in a growth equity partner, basically a family buy out to buy out my brother and sister, buy out some of my shares that I inherited of the business and then really take the handcuffs and take some risks with the business in order to accelerate and grow it, start building out the team more, start building up the functions, the growth roles. And so that was the most fun period of my life. I’m lucky to have had at once. I’d love to do it again. But I’m very grateful that I had the opportunity to be exposed to what a true growth environment meant and what it was. And ultimately to lead that environment is something that I will cherish forever. And so, we went from roughly 20 million to about 55 million or maybe it was a little higher, maybe like 57 or 58 million in revenue when we sold. We built out every function of the business. We looked at every sort of undocumented process or just things that people did and tried to create structure, tried to create basic processes, some processes were more complex, some very light, but really tried to just create a repeatable, standardized type of business so that we could truly focus on the innovation of the products themselves and the acceleration of the use of data across different types of verticals and different types of applications. And so, we needed to get the distractions out of the way of just the general structure of the business and billing and those types of things that just need to happen no matter what, we didn’t need to innovate them, just buy something and use it. And that allowed us to really focus in on the development of the core assets and core products. And so, we developed a what I would call sales driven culture first. You bring in a private equity partner or an equity partner, they want to grow the business. They want to focus on pipeline development and bookings numbers. And the best way to do that is hire sales reps. And so, there’s good and bad that comes along with that. If there’s not a lot of infrastructure to support those sales reps, well, then ultimately, there are going to be some that fail, and some that are mad, and they’re frustrated, and you’re trying your best, but naturally, if their salespeople are striking out, and they’re not able to earn commissions, well, they’re not going to have a happy environment. So, we did a great job. There was some- not every day was a great day. We didn’t do everything right. There was a lot that we did wrong. But we built, measured, and learned, and we grew and we adapted to everything that we did. And I would say we built one of the finest sales engines that was out there and then really started to try and evolve that to what is, in my opinion, the proper way to start, which would be a product driven culture or a market driven culture, what are the true demands of the marketplace, not just the demands of what you guys can go sell to customers, and really trying to be good thought leaders out there, be a forefront in what we’re trying to do. And so, we started to develop and really shift that sort of unsaid culture of the business from sales driven to being product led and market led. And that allowed us to continue to accelerate, to continue to define verticals and ultimately what found us a home at Verisk because we had found a nice sweet spot with an insurance. We had about 180% CAGR growth rate, and it was just doing very well. And that gave the buyers confidence in what we were trying to build and grow and that they could take it and do something with it.

Alex Bridgeman:  What did you take from the habits or styles of running the company, what did you take from your dad, versus what did you leave behind?

Gary Walter:  So, I would say what I took from my dad and what I inherited from him was truly the knowledge and ability to visualize and see how the data was assembled and see how the engine of the products could work together and really understand how to connect raw data, raw information into outputs that generated value for customers out there. What I would say that I learned not from my dad, and from a lot of those around me afterwards was the ability to become a professional operator of the business, to focus on a strategic plan, be a data driven organization, let the data not the opinions do the deciding of what we wanted to do. It wasn’t the loudest person that could yell to make decisions. It was really the data that helped us make informed decisions on what we should do, what levers we should pull, where this should go, really even learning what does that even mean when there are levers in the business because they do mean things. Why are these institutional investors, why are these growth equity investors, why do they look at so many spreadsheets, and why are they so important, really understanding how to look at a business on a spreadsheet and why that is important to look at it that way, to really take the opinions out of it and really look at what you should be doing and what’s right, and then developing to be good manager, I mean, just a good manager and a good growth based leader and how to treat people fairly, be transparent with them, be honest with them, whether it’s good or bad, and not play games and just kind of really care about everyone but also demand performance at the same time. It was a really great transition for me. It changed who I was as a person. I had a couple executive coaches along the way that did a great job of helping me round out that skill set, a lot of great independent board members. And then again, my intellectual curiosity, like I just researched a lot about it – what do good leaders and managers do? And quite honestly, the simpler you keep it, the easier it is. It’s very- a lot of people just very much overcomplicate everything. And it doesn’t need to be that way. What are the three or four things that we need to focus on? How does what you’re talking about relate back to one of those three or four things that we’re focusing on? Where’s it at today? What do you recommend that we do? What are your thoughts and your concerns about doing it? And really just listening to people, sharing your- I’m a talker, so I very much share my opinions back, rightfully or wrongfully, maybe overshare them sometimes. But really, once you can establish a good relationship with those around you, especially in an intangible business where you can’t touch the products, people and staff know that you care about them. That allows you to have good open, sometimes hard conversations with people. But ultimately, everyone’s trying to be aligned around what’s the right thing to do for their career, for the business. Hopefully those things are aligned together in what are the right steps to take forward. And it’s not as hard as it needs to be. It’s a lot of hard work, but it’s not as hard as it needs to be for a lot of people.

Alex Bridgeman:   There was a really good Invest Like the Best episode with Brad Jacobs that you would probably love. And one thing he talked about was that simplicity, that focus on keep it as simple as possible, don’t overcomplicate things, try to find the simple route to getting something done.

Gary Walter:  And find an appropriate cadence that you as a person or me as a person can stick to. If you say you’re going to meet with people and have one on ones, then you have them and have them consistently and be prepared for them and show people the respect along the way, and they’ll show it back to you, and they will ultimately work harder for you.

Alex Bridgeman:  What did you learn about hiring an executive team and each of these functions, the CRO, CTO? As you built out that executive team, what were you learning about hiring those types of roles?

Gary Walter:  Really not so much going from a lot of people start and they start on the process, and we did too, is you start with who you know that have a role somewhere else that fits that thing. And really, it’s fine if it works out. In some cases, it works. In some cases, it doesn’t. But what was really more important was really to focus on what we call A player hiring and then really developing the scorecards of what do we want out of this role? What do we have now? Who are the people- What skill sets do we have now? What roles do we need? What do we need these roles to do? Let’s post the role, no matter what, even if we know we have a person that we want to hire to do this type of thing. Let’s at least try to get two to three candidates just to see what else is out there and just to understand what they are- even if we already know that our friend who we’re going to hire no matter what is an A player and can get results done, at least make it fair to everyone else in the world. And maybe there’s some internal people that want to apply for that job as well. And they deserve to have the opportunity to at least have an interview for it or talk about it or understand why maybe they’re not qualified for it so that they can help keep their career on a good path that they want to be on so they keep engaged in the company. But I would say, again, just more information that you can gather before you do so that you really can think and then really taking the time to think about and reflect on what’s worked and what doesn’t work and what truly do you want this thing to do, and what do you think, what are you expecting an A player to do, and write it down. Because more often than not, you’re going to have to get comfortable with about 90% of what you want in order if you want to take these hats off and scale a business and kind of let other people do the things you work on because all of us, it’s just human nature, we think we’re perfect. Especially when we’re passionate about doing something and we love it, we think it’s the best when we do it. You can only do so much. Somebody else is going to have to do this stuff, and they’re not going to do it as good as you think you are. So, write down what you’re expecting them to do and be comfortable with about 90%, 85 to 90% of what you think is success, and that’s probably realistically 100% success.

Alex Bridgeman:  And then you’ve talked- you and I have talked about how much you focused on empowering people and connection. What were some ways that you went about doing that? How did your style of empowering evolve?

Gary Walter:  I’m very lazy. I don’t like to do a whole lot. So, I like to let other people thrive and let them take their chances and go after and do it. And so just really empowering people. It’s not that difficult. More often than not, I think one of the things that’s overstated is that we need to find the absolute best talent possible. And that is very true, but that is a hard statement for a lot of people to digest because they don’t know what the best- what is the best? What does that even look like? What does it even need to do? If you start to take a step backwards and think about it, most of the people that both I know, that you know, that are friends, are family don’t go to work to do a bad job. They go to work to do a good job. They’re trying to do a good job for the most part. I don’t think people are just trying to go out there and take from the company and do nothing and be a shitty employee. Like people are trying to do good jobs. People want to do good work. They just need to be helped and coached and guided. And yes, there are some people that just can’t do what you’re asking them to do. And then you need to identify that early. And it’s best for both sides if you just kind of move on rather than drag things out and everyone gets kind of frustrated and you really lose that personal connection with that person because you never know, it might come back around. You might need that person to do something else later and they come back, maybe not, who knows. But at least you’re leaving on good terms with everyone. But really give people a chance. Let people do it. Be lazy. Be a CEO that’s lazy, that book, CEOs are Lazy, the book. Balance out your life and your time with your family and stuff that you want to do and let people try. Once you get past 10 million in revenue, you’re not going to be able to do much more as an individual unless you’ve got something so sweet that is so ecommerce based that it takes nothing to support and just people can go through the roof and you can be customer support, some glad handing and whatever and the marketing person to do whatever you need to do. Find your zone of genius, find what you really truly want to work on, find what you’re really good at in the business itself, find the relationship. And that can be anything you want. It can be anything. And then give people a chance and let them try, trust them. I think most people will find success in that process.

Alex Bridgeman:  What was your zone of genius, and how’d you find it?

Gary Walter:  My zone of genius, well, it’s a very self-reflective process in what you want to do, balancing out what you like. Also, are you good at what you like? Is it really impactful? So, there may be something that you like doing, but you’re just not that good at it. So, then you need to take time learning it, but then that’s okay, too, as long as everything else is accounted for. How do you find it? You find it. It just comes to you. It naturally takes place. Once you start to take your hats off and empower other good people to do different functions and roles and do the work of the business that the business needs done, I think you just naturally gravitate towards that product. Like I was very good at what I would call within the industry resellers and the industry partnerships and the people that use the large referential data assets that we were- I knew that stuff with my eyes closed, and I loved it, and I still love it. And it’s great. And it’s just the building the large referential identity-based databases and being able to create great relationships out there and support them to answer any questions. We would go with the spreadsheet that every field in a file, the layout, the header, record, the definitions. I didn’t need to open the spreadsheet; I knew how every piece, every component was put together, and I just really enjoy that stuff. I couldn’t have been an attorney or an accountant, had to have this consumer data intellectual curiosity and skill set that comes around it that not a lot of people have out there. So that’s really where I could be most impactful and drive. When we needed results, while we were building out our sales organization, we couldn’t lose those customers. And so, I really needed to- and I was not- I didn’t know how to build a sales organization, but I was learning on the fly. And I got about a couple steps down the road, and then I could really run, and I could absorb information pretty quickly and do it. But the process had to get going without me. And really, the business needed me to maintain that customer base, so we could build out the client success, the account management, and the hunting organization that came along with it in order to facilitate our growth. And so, I had a really good team, really good partners. I call them partners. I don’t even know; they didn’t work for me. We worked together. We divided and conquered. We knew where we needed to go. If it wasn’t a typical thing that fell into a CEO job description, that didn’t matter to us. When I was on, people took a step backwards and let me shine. When they were on, I needed to take a step backwards and let them shine as well. And so, the ability to collaborate and have trust and support from a team around you and everyone just in it to do what’s right for the business at that moment in time to take the next steps, that allows us to continue. Every step we took got to be a bigger step forward. But it starts small. It starts with little wins.

Alex Bridgeman:  You talked about being a sales driven culture and then evolving more, maybe more into a product organization or product driven culture. Where did the sales driven culture, where did that serve you and where did it fall short?

Gary Walter:  It served us when I was the only salesperson and it was a family owned business. And so, if I sold something this month, great. If I didn’t, that’s fine. We’re on subscription revenue. It didn’t really hurt anybody. We started to build out the process. So, we started to over hire, and we hired a lot of people at one time. We also needed- and we needed those people and we needed all those recerts. But we also didn’t have training and we didn’t have onboarding, and we didn’t have a lot of- like when day one came, they came in and they’re like, what do we do? And sometimes we’re like, well, you have to figure that out. That’s when the sales organization, sales driven culture helped us. We knew how to sell. We got results done. We focused on the pipeline development. We focused on the output results that came from them. And we did not miss our bookings numbers and our quarterly targets come hell or high water. It was very- not many at all that we were off by any percentage point under what the target was. That served us well. Where it didn’t was sometimes we oversold things. Maybe our sales reps over promised things. We couldn’t exactly get the value- the customer couldn’t exactly get the value in the end, which increased churn. So, we bring in a bunch of new people- And it happens in a lot of businesses. It’s why it’s nice now looking backwards and seeing what worked and what didn’t work and what you could account for. Bringing a bunch of new people in the door, not everyone’s going to be successful, whether it be employees or customers. Onboard them, some people didn’t get through onboarding, and then they just lost the deal. And they’re like, you got to contract [inaudible 24:28]. What are you going to do? Like, if they didn’t get value, are you going to go back and sue them and make them- like we couldn’t support them. We didn’t do it. Like we didn’t hold up our end of the bargain. And it’s a very tough conversation to have that then, especially when you’re driven by snowball effective revenue that continues to compound and grow. And then all of sudden, before you- you’re counting on this number of an annual bookings number, an ACV number that’s going to start coming in, and you’ve reported that to the board, and then all of a sudden, that number’s- that customer’s left before they’ve paid you or you even billed them once. So, you have to pull that number back out of the process and then kind of explain it and make sure you had a way to fill that number back in there. So that overselling, overcomplicating, really focusing on the ultimate let’s bring as many customers as we can as quickly as possible, which is fine, which is great, but then not complementing it with the ability to support those customers or onboard or answer questions or make sure that they extracted value. We really then shifted our celebration of success from signing the contract into when we got a check, our first check from that customer. Then we knew they were getting value. Then we can celebrate.

Alex Bridgeman:  So how would you have adjusted knowing what you know now about the product and sales balance? How would your pace of hiring or position hiring have changed? How would you go back and change, if anything, about the way or pace you hired?

Gary Walter:  Very hard to kind of think back at a tactical way of doing each little hire or move that came along with it and trying to remember the exact timelines of when who came and went, when, why and where. I would really spend more time on the upfront strategic planning alongside my growth equity partners and what it truly- really, what it means. A lot of times, they have their folder, and we have our folder. We’re going to do what we do, what we need to do. But always in the background, it feels like somebody’s kind of taking notes, and you never really know what’s going in those notes. And then it just goes in the file. And we did a great job of communicating with our boards and creating alignment, creating transparency, creating trust, like everything I could do about it. I would just put more effort and more focus on truly making sure that I am aligned with them and my team is as well and really focus on saying we don’t- lose sort of what are the guys in California thinking, what are the investors thinking? They’re probably not thinking about you at all. And now we’re thinking about them. And now we’re not thinking about what we need to think about. Going off, doing more of that strategic planning upfront, continued cadence, and I’d professionalize the way we did our quarterly offsites and things like that with our leadership team and just make sure we were on the strategic path together and making sure we’re doing it. And then we would have been not so much gambling by some of the hires or risks that we took and spending a bunch of money to hire seven or eight people at one time would have been a very confident, educated guess. I don’t know that I would have gone backwards and changed. Like, we did what we needed to do, and it was successful in the end. So, it’s hard to look backwards and say, I don’t know, I don’t want to fix what wasn’t broken because we were successful in the end.

Alex Bridgeman:  What goes into an effective strategic plan, these multi year plans for the business? What makes a successful one or a more effective one?

Gary Walter:  Everyone signing in blood on the plan in the end, more is everyone aligned around it, has everyone had their chance to share their voice and feel like they’ve been able to share their opinions, whether someone’s idea or task goes in there or not. That’s one thing. But people having a voice and getting buy in on it. It can’t just be a CEOs plan. Again, there’s only so much, once you start getting to a larger mid-market company, there’s only so much that one person can do. More often than not, if you get the voice of the people, if you suppress your voice and get the voice of everyone who’s actually got to do all of this and make sure that happens on a day to day basis. Allow them to be the CEO of their own purpose and the organization, own their own destiny within that function, within that role, empower them to do it, create a good environment for them to do it, that’s really, really important. Anymore, me dictating or I believe any CEO sort of dictating here’s the plan is going to not- I mean, unless it’s some crazy growth product, it is not going to be as successful as it could be. People don’t want to be told what to do anymore, I don’t feel like, at least the people that I know. They want to- ultimately, they’re going to do- you’re going to think of the same thing that they’re thinking of anyway. Let them think of it. Let them run the plan. Let everybody have input on the strategic plan and where we’re going there. Then ultimately, everyone shares accountability and everyone shares ownership in the business. And then results will get done quicker.

Alex Bridgeman:  How would you handle disagreements? So, if you had a different view than someone on that executive team, how would you walk through or at least find a way to get to the same place?

Gary Walter:  I’d close my office door. A lot of people have different ways of doing things. I’m in YPO. We have a formal issue clearing type of process that you can do. More often than not, I think the principle that I would go to is just really in all circumstances, try not to call somebody out in front of a group and not let anyone else call somebody out in front of a group. Nobody likes that. That’s what starts fights. That’s what starts arguments. That’s what builds animosity. Try and take things, truly try to take them back to like a closed door or a small group or a one to one session and just say this is a problem. Figure it out, or I’ll figure it out. Easiest thing for me to do is replace you guys. But I had a good way of doing that because I developed a good relationship. I could say things like that. But ultimately, it’s really trying to just- your job as CEO is just to create an environment where people can thrive. Same thing here, if there’s an issue or there’s something that needs to go, just get the people in the room together as quickly as possible. Don’t let bad things simmer. Don’t let bad news simmer. Make it travel fast. Get it out of the way and clear it out. And I think if you can focus on that and ultimately focus on being a good human, not letting people feel like they’re being trashed or called out or being told that they’re dumb or something like that, without saying those words, that’s what people- that’s what I would want. And so, I think that’s what a lot of people would want.

Alex Bridgeman:  Is there anyone you tried to study? As you were learning to be a CEO, is there anyone you tried to study and take habits or ideas, inspiration from?

Gary Walter:  I find inspiration in a lot of things. There was a guy named Pickle that was an excellent sales leader that I got a lot of advice from, and I like that nickname, so I’ll leave him with that. Honestly, social media, if you focus it in the right directions, you can find the one-line quotes, the TikToks, the this, the motivational things. There’s just a lot of quick access to very synced, motivational, inspiring types of information, leadership lesson types of information. And because the phones are all listening to us, it happens to all pop up at the same time. I don’t think there was any one single person that I really dug deep on and tried to understand in doing it. I mean, again, a lot of this when you’re fighting and you’re grinding and you’re going hard is staying one day ahead of everyone else and some days faking it and doing it confidently. And then you get things done right and do them right. But not one single person. I think that’s one thing, I would go back to school earlier. I would encourage- my board encouraged me to join YPO, a professional peer group of CEOs that everyone has to be a CEO or business owner of a company larger than $12 million, of true peer sized organizations going through similar things. I would also go back to school earlier. I think continued formal education is very important for leaders.

Alex Bridgeman:  Back to school, like an MBA program sooner?

Gary Walter:  It doesn’t matter where, going into a true learning environment I think is important. Keeping the ability, it is a skill set, the ability to learn, the ability to go to school is a skill set that it does get lost once you graduate college or whatever you do and go into a workplace, you go into a doer mode, not so much a learning, listening, sitting in a chair, hearing somebody else talk, whether you agree with that person or not. I think the more your career advances, the more you actually go back and learn from that formalized environment. And maybe you learn that- and confirming what you know, that you do something better than maybe a professor talks about or somebody else talks about that does have a rubber stamp and employed by a university or a great school or shitty school or whatever, it doesn’t matter. They’re employed by them, so they have a rubber stamp of authority and empowerment, that kind of feels like the truth. Going in somewhere and having an open mind and saying, you know what, I understand what they’re saying. I think I do my way- I think my way is better. And I have data, and I have, even if it’s my own data that I manufacture that says that I do it better confirming that, that’s learning as well. And that’s a very good skill to have. And you’re ultimately empowering yourself. And I believe that that is truly important.

Alex Bridgeman:  You’ve talked about one thing you’re especially good at is the selling piece. And we talked about how the data being proprietary or not is less important than go to market and the sales strategy behind it. Can you talk more about what you meant by that and what that means?

Gary Walter:  Everybody wants proprietary data. Every investor, every company, everyone argues that they have their own version of proprietary data. I’m not going to debate that point or not, whether a source or a feed of information is truly one of a kind, proprietary or an analytical model or something like that. All those things are great. That’s opinion based. I mean, you’re never going to convince someone, if they don’t think it’s proprietary, you’re not going to convince them that it’s proprietary. That doesn’t matter. All those ingredients need to go into a factory and come out as a product. Data itself is what you’re selling, but it’s not necessarily the product itself. It’s really putting and manifesting a persona to what that thing is, creating something tangible that can be digested and understood by a variety of people out there is the most important part of it. And so, what I see in a lot of companies, in a lot of data organizations, they do these constant innovation of new variables or new analytical models or new types of things, but there’s really no- there’s not a cohesive, comprehensive tie to the sales organization and the marketing and the commercial organization. So, people who are responsible for revenue, they don’t know what’s coming off the tech platform. And then it just goes into a holding tank and sits on the shelf somewhere, and no one ever sells it. And so, you spent all this time innovating something super cool, and the data science teams are super passionate and excited about what they’ve been able to produce and it’s got all these great results that they’ve been able to verify. And then they get frustrated because why can’t salespeople sell this thing? Salespeople look at them and say, I don’t even know what it is. Tell me what it is. Show me what it is. I can’t touch it. So, if no one explains and educates me on what it is, how do I know, how am I going to sell it? I may be the best salesperson in the world, sometimes you can only blow so much smoke, and you’ve got to have some true core knowledge about what you’re trying to do and truly be an expert in that product. And so by tying those processes together, and I think one thing that a great CEO can do in a SaaS and a data or DaaS business is when you look at the scrum cycles and you look at what the tech teams are developing and what they’re outputting, look over at your CMO, look over at your head of sales and say, do you know what that thing is? What are you going to do with it? Are you guys aligned? And then let’s look at- next, let’s look at the next scrum cycle. CTO, please lay out what your plan is, what you’re going to work on, what your task lists are, hand it to the salespeople. If these guys work on this stuff, are you going to sell it? Or is it going to sit on the shelf? Truly creating alignment between that development cycle and the go to market strategy, that’s what accelerates intangible businesses. That’s how people accelerate and grow very, very quickly. Great products are supported by a great go to market strategy. Most businesses that are stuck or stalled, whether they stall out at 10 million or 15 million or 2 million, it’s because there’s not enough tie in the sales and go to market strategy and demand for growth from new innovation.

Alex Bridgeman:  Obviously, the sales team is going to be talking with customers, but a good product organization will also be talking to customers, and they may hear different features wanting to be prioritized. How do you sync up the two into one list of priorities for the product?

Gary Walter:  Painfully. Try your best. Again, it goes back to having good relationships with your teams, being able to have fun with them but also be able to speak directly to them and call them out when things like this pop up. Like you guys don’t know what each other are talking about. Like, let’s step back and really know that. Stop and go. And so, it’s finding your own cadence, finding your own way of doing it, trusting and verifying your people out there, giving a revenue target to your technical team as well and your product organization. I mean, in the end, people have to make money. So, they’re not here to do charity work. They’re in companies, like I had to do well and make money and grow that business. And so really tying everyone back not just to a bonus number at the end of the year but that product specific release or special types of stipends or spiffs or different things like that, that’s how you create alignment out of it. And there’s nothing wrong with saying to your CTO or your chief product officer, you’re commission based for this, period, because you want to spend a lot of money building this great big thing that’s really expensive, that’s very technical, that not a lot of people can digest and understand, you’ve got to help sell this thing, too. So, if you want to make a lot of money, and you really believe in this, and you’re going to do it, and you’re going to spend all this money, and we’re all going to support you on it, you have to have some skin in the game. So, tying it back to financial recognition and also non-financial recognition is very important. [Inaudible 38:48] in an organization is truly important for younger generations.

Alex Bridgeman:  I hadn’t heard of the commission tie in for product leaders. That’s an interesting way to align incentives with the sales team.

Gary Walter:  Well, they don’t want it. They’re going to try and avoid it and try and tell you a thousand reasons why it’s the wrong thing to do. But in the end, when you’re spending millions of dollars to build this intangible thing that does very complicated processing or complicated tasks that are not easily digested by everyone, ideally, we would have a bulletproof business case and alpha beta customers and everything’s dialed in and going. If you’re truly not there as an organization yet, then by God, we are going to live and die by our bookings numbers and the ability to get this product off the shelf, all of us together. That’s what growth is all about. It’s not one team versus another.

Alex Bridgeman:  So, I’d love to hear more also about the eventual sale to Verisk. I’m curious what that was like emotionally for you, knowing your father had been running the business and passed away and now you were running the company and passing on that company to a non-family member and strategic investor, what was that like?

Gary Walter:  Handing the company, handing the keys over, I was ready. I’d been doing this for 15 years, and I’m turning 40, call it a little bit of a midlife crisis that’s coming along to it, it just seemed like it was the appropriate time. Two successful sales of the business, over $400 million going in, of cash going into people’s hands that I know. And my family and my investors and my employees, and like it’s real money and it’s a real thing. It’s not like when I think about a publicly traded company, it’s just stocks kind of floating around in there, it’s a very lofty sort of concept when you think about it. I mean, this was people that I knew whose bank accounts were being really impacted in a very significant way that I’m super proud of that we were able to do. So, handing the keys over, handing the company over to someone else was not as difficult as I thought it was going to be. What I would put more emphasis on is the continued life plan after that and truly knowing what I want to do, and I would say I’m still on that journey, trying to figure out what is next, what is the right calling. Having a good amount of success and then not having those daily little successes and a little bit of the ego that comes with it in the sense of, the sense that you’re kind of a big deal or you’re a big fish in a little pond, when that’s not there anymore, there is a void and you need to think through that and fill that in. And so, there’s a lot of just different random tasks. I started playing a lot of golf together. And guess what, you’re not winning immediately at that either. So, then you start to- negative thoughts creep in very easily. And so, you have to be very intentional on what you want to do. And I would emphasize more of a pre reflective process on what is next for me instead of waiting until after – personal feelings, a lot of people approach this topic differently.

Alex Bridgeman:  What are some ways you’ve seen CEOs approach it effectively in thinking about what they want to do after selling?

Gary Walter:  I mean, there are people like Wayne Mincy, my old independent board member who just smooth as can be and moves on, just it’s a business and goes right to the next one and to be able to do it again. A lot of people move into, like I’m doing, into a coaching or consulting role. I like to do it. I truly- I was a high school teacher. I like educating. I like the mentoring process. I really like helping other people. And so, I’m finding a sweet spot in that area. It’s hard to say what success means. What I would say is just because someone does something and it’s successful, everyone just thinks, oh, my God, you got a big check, and now life is great. Like everyone, there’s still ups and downs, there’s still roadblocks. We’re all people. We’re all just people out here. Honestly, the world is driven by people of a similar IQ level in general. So, no one’s really smarter or dumber than anyone else. We’re all kind of the same. It’s just how we use our brains and how we drive forward. But people still struggle no matter what. People have good days and bad days. And so don’t ultimately always just assume that just because someone got a nice check that like there’s something totally different than anything else out there. Just treat people equally. Treat everyone fairly. Be good to everyone out there.

Alex Bridgeman:  Awesome. Well, Gary, thank you for coming on the podcast. I really appreciate it. It’s been good to chat with you more and have you on the show. Thank you.

Gary Walter:  Yeah, thank you.

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