Episode 154: Breaking the Boardroom Barrier with Tommy Richardson, Chief Product and Technology Officer at Litmos
In this episode of Product Thinking, Tommy Richardson, Chief Product and Technology Officer at Litmos, joins Melissa Perri to unveil what it’s like to move from an operating role as a C-Suite executive to a board role and how to position yourself to work with Private Equity and VC firms.
You’ll hear them talk about:
[08:17] - While private equity businesses (PEs) are frequently portrayed negatively in the media, many, especially in the software and technology sector, are mainly focused on business growth and expansion. This approach contrasts with VC companies, which may focus on early-stage or high-growth ventures. Leaders navigating a transition to PE ownership have to embrace the opportunity with optimism, prepare innovative ideas, and communicate in terms that resonate with the investment-focused mindset of PE businesses.
[17:59] - Regardless of the role you currently have, stepping out of your comfort zone to seek knowledge and mentorship from other leaders within your organization is essential for career advancement. Remember, most leaders, including CFOs and CEOs, were once in earlier stages of their careers and likely received guidance along their path. Moreover, leaders are generally supportive, especially when someone shows a readiness to take on more responsibilities. Another key ingredient is the need to be prepared and delivered when given an opportunity. Last but not least, use modern tools and techs to gain basic knowledge in sales, management, and forecasting before approaching leaders.
[22:32] - Thriving as an executive requires three critical skills: communication, practice, and expertise. Effective communication bridges the gap between technical language and investor-savvy dialogue, allowing leaders to articulate strategies and mission-driven work in a way that resonates with diverse audiences. Alongside communication, having meaningful expertise is essential. This involves a deep understanding of the subject matter, ensuring credibility and the ability to engage in meaningful discussions about complex topics like AI or software development.
[40:37] - For executives aspiring to join a board or work with a private equity business, you must achieve multiple successes in your career, as success is relatively rare in the business world and tends to attract attention. Be open about career ambitions with colleagues and networks, as this can lead to unexpected opportunities through connection. However, career advancements might not happen as quickly as you might hope. That's where patience comes into play.
Episode Resources:
Other Resources:
Melissa - 00:00:37: Hello, and welcome to another episode of the Product Thinking Podcast. Today, we're talking about what it's like to move from an operating role as a C-suite executive to a board role, and also how to position yourself to work with private equity and VC firms. I'm joined by Tommy Richardson. With over 20 years of managerial roles in large-scale SaaS systems, Tommy 's currently the Chief Technology Officer at Litmos, who specializes in corporate e-learning. Today, I'm very excited to talk to him about his professional and personal leap to being a board member and how technology and product executives can work better with their financial peers. But before we dive into talking to Tommy , it is time for Dear Melissa . This week's question.
Dear Melissa, when do you need a business case? What happens if you're not able to find the data to back your hypothesis? How do you balance getting to first mover advantage versus building the business case?
So I think there's a lot of misconceptions about what a business case is here. And it's true. Back in the day, we had to do like a ton of analysis and justification that usually didn't involve talking to customers and build this huge document to go and ask for money from executives. And that was more of like a project management tool to get funding for our projects. What we need now is a lighter weight business case that helps us support the types of initiatives or work that we want to go after. And that's what we're talking about in product management. So business cases are actually important here for helping to demonstrate that you did your homework, you found a problem to solve, and you have an idea that this problem is actually going to make us money. What I'd say is not in a business case is a whole specification of here's all the things we're going to do, right? It should contain a vision. It should contain the reasons behind what problem we're solving and why. It should contain data about what we hope to achieve from that. And it should be supported by a bunch of research that we've done.
Now that research though isn't something that gets thrown away when we start building the product. No, it should be research and experimentations we've done to prove that this is the way to go. So when I think about business cases, it could look like a two to three pager on, hey, we discovered this type of problem for enterprise customers. And we've done some lightweight experimentation with it, we've done a bunch of user research, here's like how many people this is actually going to affect and what types of metrics it's going to affect. For example, maybe your user experience is really poor, you have a ton of enterprise customers actually churning, and you go out and you interview those people who are churning or in danger of churning, and they show you the issues that you need to solve there, right? Now you take that back and you say, here's the problems that we need to solve, Here's like our approach to solve it. I wouldn't go crazy with this. Just like generally explain, what you need to do. And here's what we believe will happen. Like we think we can add back X amount of value in stem churn. Like we believe that it will save this much money because people will not be churning, blah, blah, blah, blah. That's really what we're looking at for a business case. We're not looking for like 40 pages of you outlining every little specification and what you want to build. We're looking for why are you going to do this, right? Like what's the point of us actually saying, yeah, like take these teams and go do that thing.
That's what we're looking for in a business case. And that's what good product leaders do. When you think about balancing first mover advantage versus building the business case, all the things that you do to build that business case should help you define what that product is. It should not be wasted effort. So there's no like, well, let me just get things out to the market instead of working on that business case. Like, no, you won't be able to get any first mover advantage without doing the research necessary to build that business case. Like you need to go out and talk to customers. You need to discover those problems. You need to figure out where you're going to concentrate. Like that's what I think about when I think of a business case. And all that stuff helps you build that product, whether it's a first version of it or something that you want to show to customers, whatever it is, that's what we're doing here. So we're not doing excess work to be able to go pitch to executives in this case. What we're doing is we're trying to explain the reasoning behind what we're building. So all of this should be necessary to help define your solution. And that's how you should think about a business case. If it's anything else, it's probably some kind of waterfall style PMO type thing where you had to go work to get some project funding. That's not how we work anymore, but we do justify our actions with data. And that's why that is so important to help provide strategic content. To the rest of the organization, to your developers, to your product teams, if you're a leader and to your leaders about what we're actually doing and why. And that's how I think of a great business case. Now, if you have to go fix a bug, go fix a bug, right? Like do not provide a business case around fixing a bug unless it's going to take like two years to fix it. And you want to justify how much it's going to help there. Like, sure. But if it's something little and it's something that you can just go do and you need to do it and there's no uncertainty around it and you don't need a lot of buy-in because it's within your span of control, do it, right? But if you are trying to point a bunch of people in a direction around a big initiative or some strategic context, you're going to need that business case. So I hope that helps. And let's go talk to Tommy .
Did you know I have a course for product managers that you could take? It's called Product Institute. Over the past seven years, I've been working with individuals, teams, and companies to upscale their product chops through my fully online school. We have an ever-growing list of courses to help you work through your current product dilemma. Visit productinstitute.com and learn to think like a great product manager. Use code THINKING to save $200 at checkout on our premier course, Product Management Foundations. Great. It's good to have you on the podcast. So you have been a CTO for 23 years. You have been working at a variety of different companies, and it looks like you partner with a lot of PE firms. You actually have been a Operating Partner as well, a COO, a GM, all of these different roles. Can you tell us a little bit about how you got started as an executive and what led you to start working with PE firms and eventually become an operating partner too?
Tommy - 00:06:49: Yeah, my career started as an executive in a startup company. So when you start the company and you're a co-founder, you get to pick the role. And so I was more of the technology guy. So I picked the CTO role and my other co-founder was more in the business side. He kind of picked a more CEO role. And that's when my kind of journey in the executive space started 23 years ago. And then since then, I've done a couple of startups. I've done big Co, ADP, Siemens, high-tech Teradata, and a lot of private equity, as of late. So it's certainly been a journey in the companies. It's been a journey and roles definitely have learned a lot. My first experience with private equity really came out of working at big companies, believe it or not. When I worked at Siemens. Siemens, the division I worked in, which was Siemens Healthcare, was spun out. And merged in with Cerner, which is, by the way, now part of Oracle Health, and also at Teradata. I was part of Teradata's business applications. We built a lot of marketing applications. Companies called Pardot, as an example, were competitors of ours. Marketo was a competitor of ours. ExactTarget was a competitor of ours. And that company was spun out. And so kind of going through those spin-out scenarios, you get to learn a bit more about the world. In the startup world, I certainly knew the VCs very well. And in the big Co. world, I knew public markets very well and really didn't know a whole lot about private equity until I kind of went through those experiences. Because typically, when you're spinning a company out, in a lot of cases, it's almost like an auction where you go out there and you tell people, hey, we're selling this company. And you do a bunch of presentations and you meet a lot of people. You meet some strategic companies, which are other big companies looking to buy businesses. And you meet financial sponsors, which are normally private equity. So I would say I just lucked into it. When you take a big company job, the last thing you think is going to happen is your division's going to be spun out. It happened to me twice, back to back. But the fortunate thing for me is I really got to know the private equity firms and understand the differences because there's certainly a difference between the startup VC firms, the public market world, and the private equity world on how they work.
Melissa - 00:09:19: Yeah. From going from that public world back to private equity, how did your job change as a CTO? What did you have to recalibrate to?
Tommy - 00:09:28: I think there's definitely pros and cons with those three different models. One of the things I really loved about the startup was just the pace, the energy. Everybody's in it. The side effect is you're trying to build a business and product market fit. And is it going to be a sustainable business? And you have to worry about funding and making payroll. These are all the challenges there. And in the public market world, you've got a very sustainable business. It's typically a larger business. And so you've got the pros there. On the negative side, even companies I was at where I was CTO, it's very difficult to get things done. A lot of bureaucracy, a lot of red tape. And so I like to say that the private equity world is, to me, the perfect fit between those two things. So speaking of recalibration coming out of the big co I had to kind of, good thing I did startups when I was a little younger. It feels like a startup, like it's very fast paced, very quick decisions. It's not decisions by the wing in it or whatever. It's just a decision. It's just, you're making them a lot quicker. You get the data, you make a decision, you go. And then if you learn down the road that something's different, then you adjust, which being a software person at my core, being agile, you have to be agile, in a startup and a private equity firm. But the other benefit of that is you kind of have the benefit of the big co company because these private equity portfolio companies, they buy them because they're sustainable businesses. The product is already proven to have a good fit. They have a large book of business. You know, they're profitable. They're generating cash. And so it almost like I had to recalibrate like half of me was startup and half of me was big co and sort of putting those two things together is sort of what you need when you're working in a private equity firm.
Melissa - 00:11:14: So you mentioned like with the startups, you had to make quick decisions. You had to really get that speed. What types of things were you taking from the big company world?
Tommy - 00:11:22: I think certainly the speed, like you said, in a startup and a big company, there's a level of, I would say, professionalism, technical problems that you're solving. You could imagine some of these big companies, ADP and Siemens, multi-billion dollar companies scale. How do you handle scale? Most of these companies, everybody wants to grow up and be a multi-billion ARR company a year. And how do you build the technology underneath to do that? How do you think about features and products that you can build and sell in the mass market? When you think about your TAM and your niches are all things that in a big company, you're thinking about every single day because they're real things you're dealing with. They're not theory. Oh, well, one day we've got a $10 billion TAM and one day we're going to get 50% of that. You're already at 50% of it and you're having to manage it. So I would say definitely something's very helpful in a private equity firms because most of the private equity ones, the companies I've worked with have been more growth private equity. And it's more about, okay, large TAM, how do you grow that TAM? And certainly, being software companies, the product is a key part of how you do that.
Melissa - 00:12:38: I think you're touching on something too that I see a lot of people kind of get confused about with private equity. I feel like with VCs, most of them are growth VCs. So some of them, let's say, are early stage VCs, right? And they do seed funding and then some of them are high growth VCs. But with private equities too, I think some people think there's only one type of private equity firm. What have you seen as different types of private equity firms? And I guess, how are they different than VCs? What's the defining characteristic that makes something private equity versus VC? And how does that affect the decision making and what you should expect as a leader?
Tommy - 00:13:14: That's a very good question. There are different types of PEs, and there's certainly some PEs that have a bad rap. Unfortunately, those are the ones you hear about in the news, in the articles. You rarely hear about the ones that are good, but I think the vast majority of them, particularly in the software and technology world, are really about growing businesses. And so I've been fortunate in my career with the private equity firms I've worked with, which have been Francisco Partners, Clearlake, Golden Gate, Marlin, that they've been growth-based PEs. So their big thesis is like, how do we grow this business? We think we have a great business. We think we can invest in it. And how do we double it? How do we triple it? How do we maybe even do more of that is always kind of the underlying thesis with those businesses. And it's funny, I had an ex-associate who I worked with many, many years ago. She and I worked together at ADP. I won't name her here on this call, but her company was just acquired by a private equity firm, and she was freaking out and poked me on the side, “Tommy , Tommy , I know you've done this. Can you tell me about it?” And so I got on the phone, like, “just relax. It's all good”. Again, I think it's a very good thing because thereafter, making smart decisions, quick decisions, I mean, if you've kind of been in a big company where things are kind of slow. You like getting things done. And in my experience most good people like to get things done. With the private equity world, you can have a lot of fun doing it. It's like the fun of the startup without the risk part of it.
Melissa - 00:14:52: So what do you advise your friend when she said, “hey, you did this before. What do I do?” What's your advice for leaders in that situation?
Tommy - 00:15:00: I told her, one, chill out. Everything's going to be okay. Told her the same thing I said here is most private equity firms buy companies and they have a growth thesis. And hers was making about a billion a year in ARR. It's like their thesis is they don't want to make less money. They want to make more money. You know, how do I take that billion in ARR and turn it into three, four billion? And so they're going to have a thesis from going through the selling process of how they think they can do that. But they're also looking for a lot of really smart people to help them do that. And so approach it with an optimistic mind, have your ideas ready. And when you get in there and talk to them, tell them all the things you've been thinking about that you haven't been able to get done, pull it out, put it in PowerPoint and say, here's the things I think we can do. Here are the great ideas to do. I think the other thing to try to speak to the private equity people and their language, most of them are investment sort of mindset.
They're looking at how can we grow the business. And so, as most product people, we like to talk about features and modules we're going to build. I got this great new AI fitting, we're working on and all our users are going to love it. And all of that's good, but you have to kind of translate that into, well, what does that mean? If you're going to build this great new AI tool for your existing customers, like what is it going to do to churn or retention? Is it going to be a new thing we're going to sell? How much are you going to sell it for? You know, how much of it are you going to book? What does that mean over year one and year two? And so just making sure and that's probably even true with VC folks as well. You aren't just kind of talking about features. You're talking about the business outcome of those features and things that you're going to build that are going to help the business grow. There's definitely a tip I tell everybody. Try to do it myself. I don't know whether I always get it right, but it's always something I try to focus on too.
Melissa - 00:16:50: So this is one of those things that I always tell people who want to be aspiring chief product officers. I'm like, please go learn the language of the financials so you can work with your board. And for those people who are feeling like they don't have trust with the board, it's almost always because they're not speaking the right language and they're not showing up and putting into terms they can look at. For you, how'd you get up to speed on what the language is of investors and learn those skills because they're not really accessible, let's say, or something that, let's say, a junior product manager might know unless they come from a business background. So a lot of people in technology, I feel like sometimes don't pay attention to the business side of the world. How did you approach that? And how do you make sure that you had the skills there?
Tommy - 00:17:33: Early in my career, the knock on me was I was always too technical. I started my career, I like to tell everybody, way, way, first job. Many, many years ago, I was a tester and I was a junior tester and they wouldn't even let me write test cases. I could only execute them and sort of move my career from doing that to being an engineer. And then very quickly, moving up the management track to CTO, where I was the technical CTO. In the startups, I did do the product job as well. But like when I went to ADP, there was a different group for product management. And because kind of my career path, like I went through this sort of the technical route. The knock on me was always I was very technical, which people need and they appreciate it, but I didn't understand the business side. And so I worked a lot on it back in the day before great LMSs, we have here at LMS, the company I work at today and all these corporate tools that help people teach skills. I went to this thing called a bookstore. I don't think they're around anymore. Bought a lot of books on business, read a lot of them, went back and got my grad degree, my MBA. I did a couple of years program at Wharton and their executive management and got an executive management certificate out of it.
And so I spent a lot of time and my own money picking up those skills and trying to learn the language was a big thing that I picked on. And so I tell everybody, I post a lot about this on LinkedIn and on my blog, you got to put the time. If you're looking at growing your career and doing things that are kind of outside of your natural zone, it's not going to be easy. It's going to be hard. People aren't just going to give you that opportunity. You got to go earn it and you got to prove to them you can do it. And that's just going to take a lot of outside time and money and a lot of, it's not going to happen overnight. It's kind of like working out. You're not going to get strong overnight, you're not going to get fast running overnight, but if you've run every other day for a year, you're going to be a lot faster. And it's kind of the same way with sort of picking up those skills. So definitely something I encourage people to do. You got to spend your time on it. And then you wait for the opportunities that pop up along the way where there's a project in the company that maybe you could do. That's a stretch where, hey, you're a technology person and you want to do product or your product and you want to own the PnL. Look for those projects that pop up. Along the way, when there's changes within a company reorganizations, mergers, M&A, like any of that, all of that creates opportunity. And all that skill building, all that side work that you're doing to kind of prepare yourself prepares you for those moments and just make sure that you're find some mentors in the business, whether that's your, I've been lucky and I've worked for some really great CEOs that have been very, very helpful and explaining to me all the things they've learned over their career. But maybe it’s not your boss. Maybe it's not the CEO. Maybe it's someone else in the business. Maybe it's a salesperson, if you want to learn about how to sell or a marketing person, a peer who can help you and just kind of embrace that learning and wait for the opportunity.
Melissa - 00:20:42: I always like turning to people in other disciplines inside your organization to go learn from. And I feel like people are afraid to do that, like go sit with a salesperson or go sit with a CFO and look at this. But to me, that's how you find like the most impactful data. How did you bridge for the people who are scared out there, I guess, right? How do you start those conversations? And I guess also there might be a fear of people coming off as like an idiot, right? And they want to make sure that they are a capable human being and they can do their job. So what have you found work to bridge those conversations and like go broach those conversations and go talk to a CFO or somebody else in the organization who's high up and has a lot of knowledge in those areas?
Tommy - 00:21:25: My experience is most leaders have gotten into leadership because they like to help people. And they like to teach people. Another thing someone taught me, it's obvious, right? But something you don't always think about, which is that CFO wasn't born a CFO. That CRO wasn't born a CRO. That CEO wasn't born a CEO, at some point in their career, they were where we are. And more than likely, they had some help along the way. And so kind of my experience is when you're going to people and you're curious and you're wanting to pick up some new skills, not only for you personally, but to help the company. Like, that's kind of what people look for. I know people on my team, I'm looking for folks to step out and say, “well, Tommy , hey, I want to help here or I want to do this”. I'm like, well, that's somebody with some drive and some passion and maybe a little bit of grit, which I think is always something you're looking for in a productive employee. So my experience is, yeah, maybe it's a little intimidating, but the answer is no if you don't ask. If you ask, the worst thing is it's going to be no. And like I said, in every case in my career, when I've asked, I've always gotten support and they've always been helpful. Because I think most companies, when you think about it, like they're always looking for more people who can do more. There's always more work than there are capable people. And so when someone kind of raise their hands and say, “hey, I'm willing to do more, I'm willing to help”, then like as a leader, you're kind of like, yes, especially if you're capable. Now, the other thing is like when you have the opportunity, you have to hit it. You know what I mean? You can't get up there and swing the bat and miss. That's your opportunity. You got to treat it as like prime time, whether you got an interview and you're on CNN or one of the big news networks, you got to do that interview well. You know, if you're a sports person and it's The Super Bowl, yeah, you can't throw interceptions in the fourth quarter. And so, yeah, you have to deliver. But again, I think that's where the preparation comes in. Like you have to do both. You have to ask, but then you need to be prepared. You need to do all the work on the side yourself to try to learn this stuff. And I think that's a great thing about the world today. You know, when I grew up, the internet was really young. And again, you had to go pull this stuff out of books. I mean, today, all of this is at your fingertips. And especially in the past year with AI, I mean, just the things you can learn from using like ChatGPT and some of these AI tools. I sort of equate it to, sometimes I'll go out on Wikipedia and look up something and I'll just get lost clicking on all the links and read about it. Like ChatGPT is kind of like that. You can ask a question and another question. And so if you want to learn about sales, maybe before you go talk to that CRO so that you don't feel silly or like do some research, learn about pipelines, learn about Salesforce, learn about how they forecast, learn about how they manage leads, learn about conversion rates, learn about some of the sales metrics and educate yourself because all of that is readily available on the internet today. You know, to kind of go read up and study on.
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Melissa – 00:25:13: So if you are a, let's say, product or a technical leader, and you really want to be an executive, you want to work with private equity firms or VCs or investors, right? And get that chance to present to the board. Because I think sometimes the CEOs hold that back when people can't communicate well, right, with the board. They're like, no, you don't go to the board. Like, I'll talk to the board, right? You're not allowed to. But you want to be able to present to the board. You want to do that. What for you have been like the most impactful skills that you could tell somebody like, go research this, right? Like go ask ChatGPT about this, go learn about these things. What's like your top three skills that you felt like really helped you in those areas?
Tommy - 00:25:56: Overall, well, I think learning how to communicate, as you sort of said, is a key skill as an executive, because one, you need to communicate the strategy, the why. You need to make sure that the work has a meaning and a mission behind it to your team. And you've got to be able to explain that well. But you also have to kind of bridge, especially if you're in software and technology, kind of the geek speak and all of that to people that are maybe more investment and financially oriented. And so you've got to be able to kind of go in the board meeting and then walk right out and do a code review or walk right out and have a customer discussion about some feature they want to have. So I think communication is very important.
Melissa - 00:26:41: How do you learn how to communicate? What do you do to get better at that?
Tommy - 00:26:45: Practice. Practice makes perfect. I always find it fascinating. These folks who I work for companies and we would have yearly conferences and we would always bring in a keynote speaker. And man, they were just always amazing. I mean, they had great jokes and they had good rhythm and they didn't have to read anything. It was all up here. It just felt so natural. And I remember one time I went and asked the person and I'm like, “how did he do that so well?” He goes, “dude, I do it a hundred times a year”. So practice is like most things in life. Like you do it once, you're probably not going to be that good at it. You got to practice, you got to practice, you got to practice, you got to practice. So you can practice these conversations in your own team. You can practice the board meeting before the board meeting. Like just don't roll up in the board meeting, like practice those slides ahead of time, practice your story, your speech. So I think definitely working in the practice.
There's also some great organizations. I never did them, but I had some friends who struggled with it and did things like Toastmasters and Meetups and sort of forced them to get good at communication. I think communication is very, very, very important. You have the greatest idea on earth, but if you can't communicate it, no one's going to buy it. And if you can't, it's got to be audience relevant, getting back to being able to walk in the board meeting and have a financial discussion about some feature you're building and then walk right out and do a code review on that. You're going to communicate very differently between those two audiences. Both very, very important conversations. I think the other is you got to have capability. So communications one, you got to have the capability. And so when you're in the moment, you've got to know what you're talking about. You can't fake it before you make it. You've got to be capable. You've got to be able to have the conversation. That's the hard work that you have to put in, whether that's during your working hours or as I like to tell people, if you want to be an executive, you're signing up for more than just eight to five. You may have to get up early and work on some topics. You may have to stay up late, you may have to do it on the weekend. All of that stuff just gets back to, almost like practicing on the communication, you're practicing your skills, you're practicing your capabilities so that when you're in the board meeting and you're talking about, hey, AI and how you believe that's going to positively affect the company, you're credible. You know what you're talking about because you put the time in, you put the research in. And I think people see that. The interesting thing about private equity boards is they sit on a lot of companies. And so they get to see a lot of different people. And so they do look at, well, that sounds like a good CPO or CTO, this one, I don't know, man. Like, and it could be getting back to either you're not communicating that well, or you don't have the credibility and the capability that they're noticing.
Melissa - 00:29:35: How do you build trust with your board, right, for the first time? Let's say these private equity companies come in. You're going to talk to them. What types of things should you be asking them when you're first meeting? And then how do you kind of maintain that relationship over time as an executive?
Tommy - 00:29:53: I think the biggest way is get things done. Do what you say you're going to do. I mean, those are probably important in anything in life, but definitely in business and definitely in the private equity world. And so early on, as you talk to the, let's say if you were just acquired by a private equity firm or you just started a new company, make sure you understand their thesis. Make sure you understand why they're in the company, what they're wanting to have happen, and get after that. And then very quickly start working on that and show them some progress, right? Quickly. I mean, I think a big mistake some people make is like they work on some big things that take a year or more to get done. And like everybody gets all nervous. Like, how can you break it up? And again, I'm a big Agile fan. Like I think Agile is great for this, which is how do you break it up into measurable units that are delivering value where you can go back to them and say, hey, I said I was going to do this and I did this. And here's the value that's delivered. And it's like most things in life. Everybody wants to show up in a relationship and you get trust right away. And unfortunately, with humans, that's not how it works. Trust is built up by continuing to do what you say you're going to do, being expectations over time. And I think as you do that, again, if you break your deliverables up in smaller units where, like say every month or definitely every quarter, you're getting the things done that you said you were going to do in the prior board meeting, all of that builds trust. And then if you do that over time, you may get fortunate enough where, let's say down the road, they call you up to go work in another one of their portfolio companies. Hey, this guy got what we needed to get done at the other company.
Melissa - 00:31:30: Yeah. So you've actually had that happen quite a bit with the private equity firms you've been working with. We've obviously seen you be successful in one company, called you back to go to other ones. You also stepped in as an operating partner at one of them for a while. How did your, like, what's the role look like on more of the board or the investor side, right? Compared to your role as a CTO and what can technical or product type people do as a board member or an operating partner?
Tommy - 00:31:58: That's another very good question. I think they're similar in a lot of ways. I look at like if you're a CTO or CPO, you have that role because you're proven you have capabilities. And a big part of your role, as I tell people, is you should think of yourself more as a coach, a free consultant, as I like to call myself, versus a manager where you're helping people internally, whether it's like a new product manager on how to build a business case. Whether it's a new architect on how to build some new complicated thing and how to kind of think about it. How do you manage risk out of it? And so I think a lot of the roles that CPOs and CTOs should be that fundamentally. I guess if you're a five-person company, you're probably coding and doing a lot of the work yourself. But if you've got any sort of population of engineers and product people, you're really there to help them and advise them. And I think when you think about a board role and a operating partner, they're very similar to that. And they're there to help. And if older me could go back and tell younger me something, speaking of what you and I were talking about before, is like a lot of people are scared of these people. Like, what are they there for? Are they spying on me? Are they trying to get rid of me? Are they judging me? And older me would say, well, no, they're there to help. Everybody wants to see that company grow. And everybody wants to see that company successful. And my thing is use them.
Talk to them. They'll help you. Again, getting back to most people and something I kind of learned in my career is like, there's no such thing as a perfect person. Some of these CEOs for the biggest companies on earth, they're not perfect. Their CTOs aren't perfect. They don't know everything. And I think most people are reasonable and like, they don't expect us to know everything. But the beauty is if you have a board member whose product or technology focused or you're working in a private equity firm and they have operating partners, like, go talk to them. Say, hey, I'm. I'm struggling with how to solve this problem. I've never done it before. Maybe they've done it and they can help you or maybe they have a friend who can help you leverage those resources. And again, my experience is when you go to people like that, you're building trust. And also, like, say, if you go and there's some new thing like, hey, man, I've never done AI before and you spend some time and maybe they don't know AI, but maybe there's a consulting firm they know and you bring the consulting firm in and they help you and you learn AI and then you go deliver on it. Like, that's what they're looking for, right? And then, you just built a lot of trust with those board members with your CEO as well. So I would say, as any of those roles, you're about helping people. And so I would encourage anybody, whether you're a VP of product management, a VP of product design, a VP of software engineering, go to your CTO, go to your CPO. Don't fake it before you make it. Go to them with your problems, go to them, asking them for help. And if you're CPO, CTO, not all boards have product and technology people. But if you're fortunate enough to have a product person on there, use that person. Use the operating partners because that's what they're there for. They're there to help.
Melissa - 00:35:06: Yeah, I think it's interesting how there's a lot of misconceptions out there about board members not being there to help. And I primarily do board roles now. And I am always brought in because somebody's got like a product problem and we're trying to solve it together, right? So I'm like, what can I do to coach or advise or help like the CEO? And if there is a CPO, right, like figure out what direction to go in, provide expertise there or be a sounding board. And if there's not a CPO, it's usually about helping them get one and figure out what to do in the meantime. So hiring the right people. But so many executives I meet are afraid to go talk to the board members, right? And I'm like, that's what they're there for. They're to help bring advice in, not just judge you in a board meeting once a quarter. That's not the work. The work is how do we all make this company successful? Because we've all got skin in the game, right? Like we all want this company to win. So I'm so shocked at how some people are not open to coming to board members for advice or not open to help.
You go and you ask people like, “oh”, I'll ask like, “do you want some help with this?” Or like, “what's your shoes that you have right now?” And they're like, “oh, no, I'm fine”. And like, obviously, they're not fine because I can see what's going on, right? But they just don't want you in their business. And they think that you're going to take over. I think that's an interesting other misconception about board members as well, is that they can tell you what to do and from a dictating like you should go build this and here's my stuff. And I worked for one startup once where. A board member was like, you need to have an Android app. And they spent all this time building an Android app for this board member. And nobody looked at the data. That was basically like their profile consumers. Ninety percent of them use iPhones. And this was back when Android wasn't a good phone to have, right? Like it wasn't as good as they are now. But they spent all this time and all this money like building an Android app because their board member said it. So that's another interesting question I have for you. How do you handle board members' suggestions? And how do you communicate with them? Like, no, we're not going to do that, right? And what should that relationship kind of look like?
Tommy - 00:37:15: Well, I mean, first and foremost, you always have to kind of think like we're all people at the end of the day. And like I was saying before, none of us have all the answers. And you've got to kind of realize that when you're going to talk to someone, some people look at people on the board and it's kind of like, man, they're like the hall of fame. And yeah, they're very successful people who get on boards. There's no doubt. Like you get on a board or being an operating partner, if you don't have a very good background, you've been very successful, but they don't know everything. And so I think one, just realize that when you go, there are people too. And Again, I think this sort of starts, you got to build trust over time. If you show up every day with some problem, they're going to go like, dude, I'm not doing your job at this point. So I think you got to kind of pick your moments and maybe pick something where you think it's complicated, where you can't get help maybe from other areas. Again, the example I was throwing out before, which is AI. AI is a hot topic. Probably every board and the world is talking about AI and everybody's wondering about it. The board members wondering about it, like probably a great thing to talk to a board member about it. As far as being someone who's been on a board and an operating partner, I would also say my view of that is they're there to provide advice.
The management team of a company is ones that are operating the company and making the decisions day-to-day. And so hopefully most boards and operating partners behave that way. But yeah, if you run into someone who maybe isn't that way going, “hey, I want a lot of colors on the screen”. And you're going, “oh my God, colors on the screen. That's the worst idea ever”. Probably not what you want to say out loud because you're probably going to get some conflict. But I would pull, as I like to tell people, if you're in product, you never say no. You just say, “hmm, that's an interesting idea, let me go look at that”. And so if someone asks you to put some crazy colors on the screen or maybe build an Android app that isn't a good idea, I don't know if in that moment I would have that debate. I would listen because maybe that person has a point. I would listen and try to understand, well, maybe that person knows something I don't. I would go back and spend time on it to your point and research it. And if it turns out it's a great idea, then you go back and you thank the person, man, that was a great idea. I appreciate that piece of advice. And if it ends up not being a great idea, like your Android example, I think you need to go back and have a conversation with them and say, “hey, I looked at this. I did a bunch of research on our market, on our users. I did a survey with our users, and this is what they said. And so I don't believe from the information I have that it would be a wise decision”. And again, I think with the idea that everybody is in the boat with you and everyone wants to see the company successful, when you kind of back that up with proven data, most folks would kind of go like, they'd be impressed. Well, man, I'm glad you looked at this. I had a wrong assumption. This prior company I'm working with had an Android app, and I just sort of assumed y'all needed one. And so I think for most rational people that I would handle it. I mean, I guess you could have a non-rational person, but that's probably how do you deal with that? It might be a podcast in itself.
Melissa - 00:40:31: For those executives who are out there saying like, “hey, one day I would really love to work on a board or position myself to be a board member or work with a private equity firm”. Besides learning the financial pieces, what other tips do you have for them to kind of think about like navigating their career? I think a lot of people think about what types of companies should I go to? What types of projects should I work on? Like what type of challenges should I look at? What do you think are good ways to think about your career if that's your end goal?
Tommy - 00:41:01: I think I spend a lot of time thinking about that myself. I think success brings opportunity. So the first thing you have to have is success and not just one success, but multiple successes because that goes, people notice that and believe it or not, success in the business world is a little unusual. And so I think that's definitely one way to get noticed people look for that. I mean, you've got recruiters who recruit board positions, they're looking out there at the deal cycles. Hey, this company sold. They got a great outcome or this company went IPO and they got a great outcome. Like that's what the headhunter recruiters do who are looking for board seats or a larger opportunity. So I would say always focus on that. The other thing would be make your intentions known and what you want to do share it with people. I share my career ambitions with my boss, the CEO of the company I'm at now and the companies I've worked before and even the board. So they know because everybody's networked. And again, getting back in the theory that most people are helpful people and they want to help you because someone helped them. For all you know, they may have an opportunity, another opportunity.
They may know someone in another private equity or VC firm that's looking for someone like you to be on an advisory board or on the board of directors. So I would say be open with what your intentions are. Some people don't like to do that because, oh, if they knew. But I would say again, I mean, be your true self. I think the rest of it, the reason why I sort of struggle with the question at first is like the rest of it is just all timing things. My experience is like the timing never happens when you think it's going to happen. You're like, “oh, I'm ready. And I want to do this and I want to do that”. But again, I think the time will come. Like you can't rush it. You got to be patient with it. The world needs these private equity companies and these companies need people who have proven track records on these boards. And it's really hard to find really good people. And so if you build that track record over time, you have a great success like it's going to come. It may not come today, may not come in six weeks, but it will come. And again, that'd be the advice. More advice I would tell my younger self. Don't try to rush it. It'll happen. Just stay focused on being successful, focused on great outcomes. And these things will definitely come around.
Melissa - 00:43:35: That's really great advice for anybody out there who's looking to make this leap. So thanks so much, Tommy , for being on the podcast with us. If people want to reach out and connect with you, where can they find you?
Tommy - 00:43:46: You can find me on my blog, which is techdata.com, or you can find me on LinkedIn, same calling there, or on Twitter.
Melissa - 00:43:56: Great. And we will link to all of that in our show notes. If you go to productthinkingpodcast.com and find Tommy 's episode, we'll have all those links to his profiles there so that you can go and connect with them. Thank you so much for listening to this episode of the Product Thinking Podcast. We will be back next Wednesday with another guest. So make sure that you like it and subscribe to this podcast wherever you're listening so that you never miss another episode. We'll see you next time.