From The US Navy To The Tech Sector To The C-Level, With Randy Wootton

Those who have served in the military develop a strong sense of discipline, responsibility, and humility. After Randy Wootton’s service, he made good use of these values he acquired to find success in the tech sector. In this conversation with J.R. Lowry, the former Navy pilot and Harvard School graduate talk about his inspiring transition from the military to C-level positions at major tech companies, including Microsoft and Salesforce. He also shares about his current position as the CEO of Maxio and offers valuable insights every CEO should know to make this leadership role an opportunity for continuous learning.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcast/randy-wootton

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From The US Navy To The Tech Sector To The C-Level, With Randy Wootton

CEO Of Maxio

My guest is Randy Wootton. Randy’s storied career includes military service in the United States Navy, a variety of tech roles including at Microsoft, Salesforce, and Seismic and three CEO gigs. He is the CEO of Maxio with more than 2,200 customers. Maxio is the industry-leading billing and finance operations platform for B2B SaaS companies.

Randy is also active on several boards with several charitable causes. He is a graduate of the US Naval Academy and also has an MBA from Harvard Business School. In our discussion, we’re going to cover Randy’s career beginnings, military service, working tech, CEO roles and other things that keep him busy professionally. Let’s get to it.

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Randy, welcome and thank you for joining me on the show.

It’s my pleasure. It’s great to be here.

Naval Academy Beginnings

Enjoy the opportunity to get to know you a little bit as well, so let’s go chronologically. You are a Naval Academy grad. How did you decide that you wanted to attend the Naval Academy and be in the military?

That was a long time ago but I think part of it was because my father had served. My grandfather had served in the Navy in World War II and my uncles had serve in Vietnam. I had this broad sense of like, everyone needs to do something for the republic and I don’t think it has to be the military. For me, the military was aligned with what I would be interested in doing. It was like if you’re going to be in the military with that strong Navy influence. My grandfather had a strong and so I thought that’d be fun. Go travel the world and fail shifts.

I had an adventure like a freshman or sophomore year. In high school, I wanted to give it a shot. If I could get in the academy, it would be a great option. If I did not, I’d probably go in the US. We have a program called ROTC, which helps our pay for college as well. I thought it’d be a good stage of my life. At this time, you may remember, this is before the Soviet Union broke off. There was this sense of us versus them and everyone needs to do their part and then the Berlin wall in ‘89. It’s a different dynamic since then for sure.

I’m a couple years older than you. I did ROTC. I was an Air Force ROTC person and spent four years in the Air Force after that. It was funny because you were still hearing, some campuses were hesitant to have ROTC on campus because of the hangover from the Vietnam War. You and I both saw, in our respective times, the dismantling of the Soviet Union, the coming down of the Berlin wall and all of that. When I was midway and you were probably just entering the military, it had the drawdown that the military was planning. All of a sudden, it didn’t feel like quite the same place as it was when I first signed up.

That’s exactly right. I left the Naval Academy and I would choose flight or I was permitted to go in the play program. I went into the NFO and spent a couple of years through flight school and then I was tracking. I went and did a couple of deployments over Iraq. It was tracking towards the next aircraft. It was going to come out. There’s this cool airplane called the A-12 Avenger, but to your point, they started doing the drawdowns and they cut back on all these programs.

I was facing the reality of, “It could be extra hard.” That’s when I decided to go back to the Naval Academy and teach the degree master of arts and liberal arts. I thought it was going to be a teacher and then I figured to get my first lesson in supply and demand. It was a whole bunch of supply of professors and there wasn’t a lot of demand for White men to go teach English and Shakespeare Specialists. That’s when I went to school.

Did you, at any point, foreseen that you might make a career of it in the military or were you never committed to that?

No, I was. I went there to give it a shot and try to be admiral. I thought that has some parallels to go into the corporate sector and wanting to be CEO. I was fired up and thought it would be great. Now, when you get in the military, as you know, you’re not married when he signed up in high school then you get married and life happens. There was a year were I was gone for 265 days. It’s just an intense pressure on a family. I think it takes a very special couple to make it through.

What’s neat now, 30 something years out and my friends who are still in are three-star admirals. Seeing them and the careers they’ve had and the type of people they are, both the men and women that are still in, extraordinary. They’re extraordinary at the academy. They’ve had extraordinary careers and it makes me so proud to have them as classmates. I feel the Republic is in great hands. I would have liked to stay in at the time. When I had to make the decision, it felt like that path forward was a little bit more obfuscated and then family issues, etc. It was easier for me to get out.

There was always a good rivalry between the Air Force and the other ROTC branches at school, particularly the Navy gang. We used to have some very heated and sometimes, I’ll say violent. No petitions against each other every now and then. There was one of the guys, a guy named Greg Alcorn who we knew was Gumby. He went on to become at least a two-star admiral. I don’t know if he’s still in but it just cracks me up that of all the people who ended up being an admiral out of that group of Navy ROTC guys who are in my year at school. We had one called Gumby who became the owl.

We had a guy named Gumby in my section. Where did you go to college?

I went to Duke.

That was the very strong ROTC program there. I had very good friends from the Navy ROTC program there. That was one of the options that I was going to go to but I went to civilian school. A wonderful school and a wonderful program. I think it’s a great option. It helps to pay for school. It gives you a little exposure to the military. You have two years. I think it’s two years in ROTC too to decide whether or not you want to continue honors or is it just one year?

It went from 2 years to 1 year when I was in school. I have no idea what it is anymore.

At the Naval Academy, it’s two years. You get one year harassed and then one year being what they call youngster with not a lot of responsibilities. Only being a student with some military before you sign up for five years minimum after school. It’s a great program. We need more people going through and having some military background, especially those in Congress. Before we send our boys and girls off to war and nicest people in Congress that are represented by a sample of veterans.

Harvard Business School And Civilian Life

You and I also share that we both left the service and went to Harvard Business School. You mentioned one of your motivations was looking at the supply and demand for English teachers or maybe professors in general. How did you find your HBS experience in terms of preparing you for that in military to private sector transition?

It was great. I’ve been at the Naval Academy. I started a business program, a night program in Maryland and thought that I was going to stay in the Maryland area. A friend of mine said, “Randy, you might want to try to get to Harvard.” “There’s no way I can get in.” He said, “You won’t know if you don’t apply.” I applied to Harvard and I think I applied to one another. Maybe it was Stanford, because I was older. I was 28 at the time or something.

As you know, what’s interesting about Harvard is it’s a general management program. I did a study while I was there. On average, 5% of the class comes from the military and 80%-85% of the class is service academy. The challenge was most coming from West Point, so I wasn’t going to publish that article but I do think they have a strong recognition of the small unit leadership that all of us from the military bring in because they’re a general management program.

I found of going there, there was a good group of people. It’s a large class of 800 people, but in general, there was some camaraderie with the other military folks. I do feel like I worked harder than anyone else because I knew the lease going in because I had no corporate experience going in. The general management program was a good foundation for building and a starting point to go into a classically consulting program or the banking program, where you go to training after business school so you get another couple of years of training which is where I was tracking.

I was going to go work with banking and consulting. At the time, I was in ’98-2000’s, the internet had taken off. In 1997, it felt like if you were in the internet, you’ve already missed the internet. I joined a company founded by an HBS, a Duke ROTC guy named Mike, who went to HBS in ‘97. He started a company back in Seattle. I took the pack less chosen to go to the startup world. At that point, the first job I had was product management, product manager. And I felt that the training that HBS should give in terms of competition and strategy, pricing, packaging, operations, and modeling was a great base skill set for being a product manager.

You weren’t a consultant but you were applying a lot of those same skills to analyze in the market, working with technical folks, and writing business requirements. I thought it was a great training. The other thing it just gave was for someone making a transition from the military sector in the corporate sector. It gives you two years to decompress to learn what the corporate sector is like, meet a lot of people and then you get the great privilege to do a full-on job search. You get an enormous amount of resources behind you.

When I was at the Naval Academy evaluating whether to go to business school or go into corporate sector, it’s overwhelming and trying to think about how you run a job search, how do you get context, and how do you get people to call you back. All I can tell you is, my dad and I had a knockdown drag-out fight about going to HBS. I didn’t want to go because it was going to be too expensive. I didn’t have money.

He told me it was going to be the most important thing I ever did and that was inconsequential in terms of a lifetime earning. I didn’t understand that and I went and he was 100% right. I would encourage anybody who can go to one of the top five schools. If you get in, go. It is life-changing. It gives you the opportunity to change location, function, and industry. The other thing you find is a lot of top employers use the business schools and screens for their applicant pool. When you’re at one of those top schools, you are now in the consideration set for these roles that you wouldn’t be able to get to if you hadn’t gone through the program. It’s so incredible and I feel very grateful and fortunate to have the opportunity to go.

Tech Sector: A lot of top employers use business schools to screen their applicant pools.

I certainly feel like I got an awful lot out of it. Coming out of the military, I didn’t have the experience that people who had been two years in investment banking or in consulting or even in other private sector jobs had. I learned an awful lot. I underappreciated the networking benefit of it at the time. I got married. I had a stepdaughter. I was like entrenched in family life all of a sudden and didn’t do this social stuff that I wish I’d been able to do or made time to do, but I got an awful lot out of the program.

I took the more traditional route out of there. I went to work for McKinsey and it was a little bit. I would say that the seeds of the tech boom were just starting. I graduated in ‘94, so a little bit ahead of you. By the time ‘97 rolled around and everybody was talking about the dot-com boom, I had three kids, so I was pretty much feeling constrained about my ability to go take a flyer on a startup at that point. I missed that cycle.

Similarly, I was studying so hard, I probably didn’t do as much socializing. I know I didn’t do as much socializing as my banking and consulting friends because they get crank out models and I was still trying to figure out how do you plug formulas into Excel. Since then the other thing I would say that’s been interesting is, I don’t think I would have the job I had without having gone there. I don’t mean that in a way like you couldn’t be a CEO of companies without going to HBS.

I do think it’s one of those even at this far in my career, people look at it and they’re like, “He’s smart.” It’s just like you meet other HBS people or even stamp. It’s like Army-Navy rivalry. Everybody’s a rival from the different business schools but when you are evaluating candidates, everyone is inclusive of people that have gone to business school and appreciate the training that it provided.

It’s undoubtedly an accelerate write it, as you said earlier. For better or worse, people do use where you went to school as a screen and probably should use it a lot less than they do. I think your dad was right, in the scheme of things, you make it back many fold. That’s particularly true for those of us who didn’t have the business experience pre-business school and having come from the military. I got out of it probably in a different way than people who did come from consulting and maybe didn’t even need to take those two years off. How did you find the private sector when you got into it working with other HBS grad that you mentioned?

The funny thing, as I talked about in the military, I have this saying that you learn to lead, follow or get out of the way. It’s critical in the military to know who is the person who’s going to make the decision and it doesn’t always have to be the leader as a signed by rank. There is always clear about the decision-making and who’s calls. You also need to learn how to be a good follower.

In the programs that you and I went through, that first year at Naval Academy or first year at ROTC, you’re learning as a plead or as a freshman to be a follower. As long as you’re giving you legal orders, you need to do it. That clearly helps cut through a lot of the BS especially when you’re in a situation like flying over Iraq and worried about getting shot at like you’re going to follow the flight lead and you’re not going to say, “We should do X.” No.

In the civilian sector, you’re not dealing with life and death but what was hard for me to get used to was, it was lead, follower, and let’s talk about it. I was like, “What do you mean ‘let’s talk about it?’ We need to make the decision. Who’s going to make decision? Are you going to the make decision? Am I going to make the decision? How are we going to make the decision? Why do we need to have a meeting to talk about the meeting?”

It took a while for me to appreciate the more nuanced network or joint accountability that you had for different projects and how do you bring things to market. You’ve got the product person, the PMM, and the salesperson. Everyone’s providing a perspective and I would go nuts completely. Someone makes a call. I’m happy to execute but let’s move forward. There was a period of time where I had to dial up listening and dial back the intensity, default to action and be more patient. Especially when I went to Microsoft.

In the startup, they just appreciated having people on board who are scrappy and wanted to get things done. Even if it wasn’t the right thing, it was like, “Go get something done and let’s learn and move forward.” That’s a magical stage in my career. Since being in a big company, I’ve selected to be at those companies that are still in that growth stage at serious B and series C because I like that phase of we’re still defaulting to action in trying to get things done, versus more of the bureaucracy and you got to influence and go around and get alignment in some ways like the government that some of the bigger companies I’ve been at.

That’s number one, we follow or get out of the way or lead, follow, and let’s talk about it. The other big transition that I think in the military you attract a lot of type A. In the corporate sector, there’s a broader spectrum of personality types, so doing things like Myers-Briggs or DISC or insights. I’ve used those throughout my career to get a better appreciation for people who have a different perspective in how they to communicate, like to be managed, and how they approach problems and building that for respective was probably not as appreciated in the military. It was like, “This mission, go get it done.” I think more EQ versus IQ and gumption and get things done.

There’s more nuanced in the private sector. It’s not a command-and-control model for the most part. To some extent, the military is probably softened a bit as well. Although, I can’t say that from first-hand experience but there’s a benefit of both. When you’ve got to make life and death decisions, you can’t sit around and go, “Let’s talk about it.”

I think that’s right, and that the key is getting clarity on how a decision is going to be made. I do spend time with the executives on the staff talking about what is the decision we’re trying to make in how we’re going to make. Is it your decision? Is it my decision? Is it a group decision? Trying to get people to step up and say, “I got it.” “I got the ball.” That’s another trait. The people at least I knew in the military in the officer ranks in particular, they took accountability. They would say, “I got it.” “I own it.” “I’m going to deliver it.”

In the corporate sector, it tends to be a little bit of the, “I don’t want to take accountability because I don’t want to be wrong or I don’t want to make a mistake.” Shining the light of we needed to decision to be made, who’s going to do it and using it as an opportunity to help groom younger people to step up and take the ball and run with it. You have to have a supportive environment that enables them to mess up and help turn it into a learning experience, versus getting crushed. I do think that is probably one of the key benefits you can bring from more of a military orientation into the corporate sector.

You mentioned a little bit ago you ended up at Microsoft. You go from small company to an arguably the biggest and perhaps most important tech firm at the time. What’s that transition like?

It was cool. I had been at this small tech company. I’ve been a product manager. I’d run a business unit. This is where I opened up the international division. It’s when we moved to England and I was opening up Asia Pacific out of Australia. I was thinking, what’s my next thing and I had a friend that Microsoft who called and said, “Randy, we’re starting a new thing.” They’re rethinking how they’re going to do ad tech and search specifically what was now being searched.

I just thought it was going to be this cool opportunity to scale and to operate at a different level, where I was running a small team. It was called Avenue Quantum. This would be an opportunity and grow big team. We’re going to hire 180 people in eighteen months. I thought it was going to be just an extraordinary opportunity with a lot of resources to go do something at a different level in terms of impact and it was true.

For me, at a stage of my career, to be able to do that, and you went from a $10 million budget to a billion-dollar budget. It was a radically different order of magnitude. Now, to the point, I had to learn how to work people and do all that, but it was just incredible. We spent $2 million to hire 180 people in eighteen months. I was hiring in France, the UK, the US, Japan, and Australia. It’s just crazy. All the city becomes this global citizen. Working with one of the largest tech companies in the world was just empowering and it also broke me.

It was the first time in my career where I wasn’t able to stay on top of everything, which is something, again for military people in particular and those that are wired in those type A where you can stay on top of everything. You get to a certain level of scale with multiple levels of management. At the time, 3 or 4 levels of managers below me that I was running an organization. I couldn’t be on top of everything and it was great because now as a CEO, that’s the number one thing you realize, you can’t do it by yourself.

You got to figure out how to bring executives in who have deep functional expertise and how do you set up a system to create transparency, accountability, and alignment. I talked a lot about better and stood it theoretically, but until I reach that point, for me at least, where I wasn’t sleeping at night. My wife thought I was an ogre. I wasn’t feeling successful. I did broke and it was after that that I got to see this is how you run and an scale organization.

At one point, I read Larry Bossidy’s book, we’ll get it roughly right where he talks about the three things you do as a CEO. As you set a vision, you pick the right people and you establish management processes. It goes in line with what you were just saying, Randy. You can’t know everything and you certainly don’t know everybody’s jobs. They’d know them better than you do and you’ve got to establish the conditions for success. Not necessarily be the one who’s personally driving it. A lot of people coming up to the ranks hit a point where the like, “This is different.”

That book is Execution. It’s one of my favorite all-time books. There’s a couple of other ones out. There’s a guy named Joel Trammell, who is a very seasoned CEO from Texas. He’s got these great texts draw and he’s wrote a book called The Chief Executive Operating System, which I wish I had gotten before I started my first CEO because it talks a lot about what it means to be a CEO and CEOs a unique job. Maybe we’ll get into that a little bit.

There’s other things out there like the Entrepreneur’s Organization. EO has a program called EOS, the Entrepreneurs Operating System. I do think, to your point, and Bossidy’s point is conditions of success, or I think of it is a system. What’s the strategy? What’s the structure? What are the roles and responsibilities? What are the process systems and tools that you need to support that? What’s the incentives you put in place to drive that?” I think that came from Galbraith’s Designing Dynamic Organization.

You think about what you’re trying to do is set up a system or an organization for success with rhythm of the business, scorecards, OKRs or whatever. I like that. I like that whole challenge in terms of how do you bring alignment. I saw Marc Benioff do it masterfully at Salesforce with his whole V2MOM construct, which again, we could talk a little bit about. I would sit in a room with 600 other senior managers at the time.

They would bring 600 managers together and Benioff would walk through the V2MOM like, “These are the objectives. Does anyone disagree?” They order in which they’re ranked and they only have any questions about what they’re meant to do. You go off and you would create your own objectives for your own team. At some ways, I was like, “This is worse than any military exercise I’ve ever been in.” It’s mind numbing to be in this room for eight hours.

At the end of that time, the insight was he was investing that time and that management cadre so that we all knew in our core what we were trying to achieve as an organization. We were responsible for going and doing something similar within our teams and our organizations. Bringing that alignment in terms of what you’re describing, that broader conditions of success. Benioff was masterful at it.

I’d be curious to get your view on Salesforce versus Microsoft. When you went to Salesforce, they were growing like crazy. In just about any other era, they would probably be viewed as the most massively successful tech firm out there but everybody zeroed in on Facebook and Google at the time. It’s been an incredible growth story. What was it like being there? How would you contrast it with Microsoft?

Genius Of Salesforce’s Culture

I was at Microsoft the tale end of the Bill Gates-Steve Ballmer age. There’s a woman out there that’s written this book about genius culture versus growth culture and I think that Microsoft optimize genius culture under Gates and Ballmer as well. The smartest person in the room set up contest between teams and developing similar things to see who would win. I wasn’t a corporate vice president but I was in VP when I left and I said at the meetings I was in, it often felt like the Octagon or Machiavelli’s Prince that you’re in this room with some of the smartest people in the world.

The way they get ahead is by destroying people in the meeting and show why their ideas aren’t right or why they could be smarter than the other person. It wasn’t what they delivered. It was how smart they showed up. When Satya Nadella came in, who I knew because of where I had been, he wrote a book. I would tell you, the people that I’ve known at Microsoft for many years say he was a street chain in terms of the culture after he came on board. Within four years, it was a completely different company.

Talk about how he went from a know-it-all to a learn-it-all culture.

That genius versus growth. Growth is where you’re bringing people together and trying to get the most out of them. I think in Salesforce, even though you’ve had Benioff who was brilliant, I do think it was a little bit more oriented to the growth culture. I also think it was just nicer part of that and the thing I liked about. When I was at Microsoft, there was a study published that Microsoft donated more per employee than any other company in the world, but it was very private.

Your philanthropy was done through like the United Way and you did these other things but it wasn’t a mandate from Ballmer or Gates to donate and be generous. They did their own philanthropy and then locked to other people. They did it as well, so you had that community. When I went to Salesforce, it isn’t Salesforce’s DNA. They have this program, the 111 program, where they give 1% of the profits, 1% of the software, and 1% of their time to growing profit endeavors.

Every management meeting you would go to, you would start off by doing some service project. It was like being in the boy scouts. I think this is so different, this orientation towards service. Benioff had this idea of service to customers, service to employees, and service to communities. It’s part of the reason why he invested in San Francisco and those buildings in a very expensive real estate. He was invested in San Francisco.

I think that orientation allowed for this, where we’re doing well and we’re doing good. We’re doing well as a company. We’re doing good for our communities. It attracted a certain type. You had to be want to do that. For military people in particular, who default to service like that’s part of what we went to serve the Republic. It was an amazing experience to be there at that time. It fostered more of a growth culture than genius cultures. Even though Benioff was brilliant, he was surrounding himself with these people and trying to create experience where they could be their best. I didn’t have a lot of interactions with Benioff. I would say, it was a palatable difference in culture pre-Satya.

From there, you got your first CEO role?

I was doing okay at Salesforce but I didn’t feel like I was operating at the scale I wanted to and I got recruited to be the chief revenue officer at a public company called Rocket Fuel because they wanted to move from an ad tech media arbitrage business to a platform business. I had the ad tech experience and I had scale. They just bought a company. I was going to help them run that and they let the CEO go 30 days after I started. I had no idea. I was like, “Folks, you’re killing me. I left a great job of Salesforce to come to you and I don’t have a CEO anymore.”

The chairman of the board, a great guy, Monte Zweben. He became a mentor of mine. He said, “We’re going to do a search for six months. You can be part of the process to see who your boss is going to be. You can always leave if you don’t think it’s going to be great.” I was like, “Okay.” I put my head down and worked. They came to me after six months and said, “Randy, would you consider being CEO?” I said no. I thought I needed to go be a COO especially of a public company, but then Monte took me aside. He said, “Randy, they’re very few public company CEOs. If you ever wanted to do this, this is the opportunity and we can do it together.”

To our earlier conversation, for me, it felt like a CEO was a captain of a ship or maybe not an admiral but it was certainly like the opportunity to be the guy. With Monte’s help, I took the next step and he was executive chair for 3 or 4 months and then he gave me the reins and said, “You got it.” It was terrifying. I felt like an imposter from day one. I freaked out by the responsibility for a public company but I’m grateful for it in hindsight that was a first experience.

I got to sell the company. I would take a private. It was hard. There was a reason they didn’t find the superstar CEOs who want to take this job during the six months search because it was a tough situation but that’s how you get the opportunity. Back to our other conversation, like if you want something hard done, you can find out who’s willing to take accountability. You’re either going to die on the hill or give it your best shot trying. There’s a lot of hard work.

Tech Sector: If you want something hard done, find out if someone is willing to take accountability and can give their best shot no matter what.

Lessons Learned As CEO

What were some of the hard lessons that you learned in your early days as a CEO?

One of the lessons learned was, because I had been up here of the people who I was now going to be their boss. That was interesting to make that transition and to recognize that the people that were on the executive team were all very seasoned executives. Back to our earlier point, the engineering leader had forgotten more about engineering than I ever would known. I’ve been a multiple times CFO. Go down the list of all those executives on the team who were very senior in season. You just have to have a lot of humility there and say, “What I’m responsible for is helping to drive the strategy and vision and makes sure this team works well. I’m not going to tell this engineer how to do his job.”

Whereas, now I’ve been around for a while, I can have a head of engineering. I know something I’d be able to poke at it, but then, it was like, “Oh my gosh,” because you step into a CEO role. I knew finance from business school but I never gotten into corporate finance or been doing a lot of looking at public company’s financials. You’re completely reliant on the CFO to know and be that T-shaped expert o r G expertise as a controller, cash and managing all of that and helping you, as a CEO, be good especially at the public company earning calls.

There’s a trust factor. There’s a humility that you have to bring to the job. The other thing, as CEOs, I recommend this to everyone. You need three things from your CEO. Three things to think about, one is you need a mentor. Someone who has been in the stage that you’ve been in and can help coach and provide insight and perspective on what’s happening. I had a guy, Tony Zingale who had been a public company CEO.

He led a couple of turnarounds and he became my mentor. I think you need a coach. A coach is someone who’s helping you with your inner interpersonal effectiveness and learn how to be a better CEO. For me, what that meant was, I had a guy, John Bear, who had worked with Apple Executives and had a lot of experience working with boards. He helped me learn how to manage a public company board. Very seasoned people on the board like uncles to me. Also, I’m the CEO and how do you manage those relationships you’ve never done those before.

The third I recommend is join some peer group. There is EO for the early-stage folks. YPO is another one. I did Vistage for a while and Alliance of CEOs. I’m in one now called Venwise, but there’s just value in being in a group of other CEOs that are in your same contacts and stage and habitual a little bit but also be able to share situations and get feedback without it being the board and without being your executive team.

After doing it a couple of times, I would say there’s another group that’s worth having, building, and nurturing. It goes back to our business school stories. I’d say get a group of personal advisors. These are people who’ve known you for a long period of time, know who you are and know what you saw in your life and the decisions you’ve made. When you come up with some crazy ideas or some new job you want to take, they can call BS on it and say, “This doesn’t seem in line with what you said you wanted to do.”

Having your personal advisory board is important to invest in over time. I did that and as I thought about moving from Rocket Fuel to my next gig, they were helpful in helping me sort through the opportunities and which one I wanted to go after. Those four dimensions of investing yourself are important as the CEO.

You had those couple of CEO gigs and then the second, you sold to Seismic, then you go in back into a larger company. Not quite certainly as big as Salesforce, but a predominant player in its space. What was it like to go back and not being the CEO?

It was delightful, I got to tell you like getting out of the CEO space, having done it twice and getting the opportunity to just sit back. I worked hard. I was chief strategy officer. I was able to build a new skill set around M&A, corporate development, which I haven’t done before. It was something I wanted to do. We ended up deploying $300 million in capital and bought two companies to the strategic investment. That was awesome.

I got to leave strategy in partnership with the CEO, Doug Winter, but run it as a chief of staff. The COO as a type role. I got to do some cool stuff but I didn’t have to be the guy. It was nice for two years to watch a great CEO, Doug Winter do what he did and watch him manage the board. Not have to be the person with all the answers and watch him in the executive team and not be the person that had to bang heads. I had to be in my role and participate as a leader on the executive team. I wasn’t responsible for holding that container.

The two jobs I had previously were intense. They were each about two years long. I jumped from one to the next and it was like intense long tour of duty. Getting at sea and getting what I call the short tour, be back on shore, and little chance to decompress and think about what I wanted to do next. I was there for two years and it was a great time. I learned a bunch and I felt it was a nice rounding out of C-suite experience. I’ve been a CRO, CEO and a chief strategy officer. Now, I’m ready for the third tour as CEO. I felt better prepared.

Now you’re in your third CEO gig at Maxio. Tell us a little bit about Maxio and what you folks are aiming to achieve.

Maxio is the mashup of two companies. SaaS staff is in charge. We’re focused on the B2B SaaS software services space. Our billing solution primarily oriented for early-stage startups. That optics was more like invoicing and red reckon reporting for companies that are greater than 30 people. The Battery Ventures of top B-C but they also have a majority on growth equity practice. Bought the two companies and brought them together in 2021. The great CEO sold it. He went through the process but he wasn’t as excited to be part of a PE mandate going forward.

They started looking for a new CEO and I met him in the middle on the screen of 2022 and joined him in June 2022. The remit was integrated technologies, integrate the companies, figure out what the strategy is and set it up for success. Part of the reason I took this job is because my first twenty years where in the corporate sector. Whereas, in go to market tech, ad tech market, sales tech and going to Seismic. It was interesting but I was like, “I don’t want to go back and do another ad tech company.”

I also knew that if this worked out, like my next phase of my career, I’d like to be an operating partner or a PE or something along those lines. I thought going into a different industry would allow me. You did at this McKinsey. You start to pattern match across different contexts situations. Going to the office of the CFO was going to be new. Could I take my go-to-market shops and apply it to new contacts? If I could do that, then whenever I wanted to go be operating partner, I could tell the story that I’m not just a mar tech guy. I’m a go-to-market executive that can help companies.

That was the intention. I always just talk about operating at the edge of my own ignorance. I didn’t know a lot about the office of CFO. I’ve learned a lot. I still have a lot more to learn and about the technology and how to sell the CFOs. I’m learning a lot, which is great. We had about 2,220 customers worldwide and 240 employees. Again, it’s one of these global remits. How do you build teams? We have a team we’re building out in Buenos Aires and in the Philippines. It’s been great.

Think of us like a series D company and we’re making some investments. We’re looking to do some more acquisitions. I’m putting those pieces together of having done M&A at Seismic. I have not done as much as bankers have but I have a perspective on how to do M&A and how to do integrations and make them successful. I feel like the pieces are coming together in this role in a very nice way.

How have you found the dynamics of being you? You were put in there by Battery Ventures. How are the dynamics different from being CEO in a public firm or you’re prior CEO situations more generally?

What I would say is, whenever someone’s putting a CEO and something’s wrong. You’re not replacing a CEO at a company that’s doing fabulous. Often, the investors don’t appreciate or fully know why something’s wrong, so that’s what they’re looking for, is someone to come in and care it out. In the first 90 days, you’re spending time just poking, prodding, asking questions, and trying to develop a hypothesis about what’s not working and what needs to happen. Inevitably, it’s worse than what people thought. That’s part of the job.

I would say, the third time, I feel more confident in how to approach the systemic review and assessment across the different functions. You’re looking at efficiency both of the teams, the leaders, and what are the right sequencing of steps you need to take. It’s also change. You’re the new guy and there are a bunch of people have been there that went through the acquisition and had all the hope and aspirations of what they had been not promised but presented and things aren’t heading in that right direction. How are you going to make it happen?

Unfortunately, these things usually evolve some turnover on the executive team. I always hope to be able to keep as many as possible. At Maxio, what was interesting is vast optic is in charge of fiber about the same size. Say they were both about $12 million to $15 million. You bring them together, so it’s a $30 million company that’s growing but none of the people had seen that movie before. Unlike an M&A transaction, it was an MOE, merger of equals. M&A usually have a bigger company.

You tap one in and you say, “Here’s our dearest system. Here’s our Salesforce system. You need to go do it the way we’re doing it.” We’ll be nice to you people and help evolve the cultures together, but this is the way it goes. When you have an MOE and you don’t have a CEO driving it. Everything turns into a debate. It’s like, which jurisdiction should we use? Which process, notion, or whatever are we going to use?

Tech Sector: When you have a merger of equals and you do not have a CEO driving it, everything turns into a debate.

There’s a lot of lost time and time. They were just significant decisions because they were required to work for one team or the other. They weren’t significant decisions in creating enterprise value and we could have moved a lot faster. That was part of the challenge. You’re turn to do the executives and your establishing a new culture. You’re bringing new people on. What you’re trying to do is create a new way, a new world, the Maxio way which is, I don’t care if it came from the SaaS office to charge by. What’s the best option? Let’s go with that.

Now, everyone’s getting on board, but at the same time, you need to be sensitive to, if you too many decisions are made that favor the SaaS optics team versus the charge by team. The charge by team feels like they’re being disparaged or not valued. Back to our earlier conversation, I’m not great at this but trying to be emotionally presented, sensitive, and bring people through change, the whole change management and recognize where they are and how to move them into a different headspace in a new future.

It’s hard. I came into a company that had done a merger of equals. I would say that people didn’t always agree on everything. The one thing they could all agree on is doing a merger of equals isn’t a bad idea.

Back to school, the Rodney Dangerfield character. He does a triple Indie dive where he dives on one dive. He does a flip and he ends up another dive and he does another flip. It’s called the triple Indie. It’s impossible. I had some banker tell me, “You did MOE? We call those the triple Indie.” They never work. I was like, “No one told me that coming in it. I thought it was just M&A.”

What’s interesting, as you end up and you probably have the same experience. As you’re building this collective, this wisdom, hard-earned battle scars, and more wounds. You don’t know what it’s like to be CEO until you’re a CEO. Now, once you become a CEO, you start this whole new chapter. You’re doing all this learning but you don’t like a long-time being CEO. Now, some people maybe CEO because they were founders and they’re CEOs for twenty years but, for me, I don’t know.

Unique Role Of A CEO

Maybe I’ll have another gig as CEO. I’ll have ten years of CEO experience in total. Not a lot of time to learn and become an expert in CEOE. I’m working on this book, the 8 Secrets of Success for the SaaS CEOs. Part of the issue with being a CEO is you’re learning all these things and it feels like, “It’s very perishable.” I’m learning with how do you share the knowledge more broadly, so I started a book until the 8 Secrets of Success for the SaaS CEOs.

It’s hard earned of things I learned. We can talk to some of them, the principles but I’m trying to make it very practical and for people to take away because you don’t appreciate what it means to be CEO until your CEO. Anyways, I feel like there’s a short period of time where you get to be CEO and then you move into board member or operating partner on the other side. I’ve been board member a couple of times, which has been fun.

Maybe going back to the military metaphor, you only get to be CEO of the Squadron for a short period of time. If you talk to anybody after they’ve done their CEO tour, CO tour of the Squadron, they talk about that other than being a Junior Officer flying jets with your buddies. that’s the best job in the Navy. It’s the same thing probably for people that are captains of the ship but when you get to be able to that, you don’t get to do it that long.

As soon as you get comfortable in the military, they’re moving you.

If you’re doing well, they’re moving you up to tag or up to the next stem. In the corporate sector, what investors want for me is to come in and write the ship. Get it going in the right direction and then figure out what the next evolution is going to be. If it’s a PE firm that owns us, there’s going to be a transaction. It’s either going to get another PE firm or to the strategic. How long is that? Is it two years? Is it five years?

My first two gigs or two years each. This one’s going to be a little bit longer, but probably not going to be ten years, which is a very different orientation than if you’re founding founders/CEO where you might do that for 10 or 15 years. This is your passion project. You converted it. You were smart about equity. You have the vision for where it needs to go and you continue to move forward with that. I have some very good friends. I was on the board guided financials services. It’s a large company. They did a transition of the two founders. One guy’s out and one guys in. It’s all amicable, but they’ve been doing it for many years. Very different than private equity or VC-backed startups in terms of what the remit is, the CEO, and what success looks like.

What do you do now to continue to develop yourself?

A couple of things. One, we talked about I taught literature at the Naval Academy. Every company I go to, I have a book club. We read books and I encourage it so people will pay for the books, have them read the books and have conversations. Operating at the end of your own ignorance is important. I have a coach. For example, I have a coach who is a multiple time head of engineering because it’s one of the areas I’m most blind. I can’t call BS when a developer tells me, “It’s going to take three engineering man months.” I want to get better at the questions that I asked.

This coach is helping me think about structurally if you’re this size company, you want to grow to $100 million. What are the systems and tools you could replace? It’s not that I don’t trust my head of engineering. I just want to be better equipped with insights about what that could look like and how do you think about growing and scaling that. I feel comfortable with marketing sales and service.

Even finance now at this point and HR. I know they’re eight functions. I’m missing some. Rev Ops and dev ops, all of that I feel pretty good. It’s still product as a product manager. I feel good about overseeing if you’re writing good product requirements. It’s the delivery of code that I feel I still could develop more capability.

We all have these functional areas that were deeper and ones that were less deep. Investing the time to continue to learn those things is going to continue to make you a stronger general manager in the end.

I hope so. Going back to that T-structure. Pick one. I do think that’s something for your audience. If you want to be CEO, this is like when I go all the way back to the Naval Academy. I got this book before going to the Naval Academy like a freshman. It did a profile of the classes that were accepted at the Naval Academy. All the things they did, like how many varsity letter winners were? How many Eagles Scouts were? How old are these things?

There’s several of those I looked at and I said, “I’m not going to be an Eagle Scout because I lost that.” “There’s this thing called Boy State. I could go do Boy State.” I structured my high school career in part to make myself the best applicant I possibly could be to the Naval Academy. I was going to be a great applicant for any school with that background but it was like, I was totally tailoring it. For a CEO, one of the things is if you want to be CEO, look at what CEOs have done.

In general, what you find is they come up either through sales, finance, or product engineering, especially in SaaS. I was a product manager early in my career and I realized I wanted to be on the side of revenue. My path to CEOE was going to have, I started off in service, I brought it into sales and got into marketing. I was very deliberate and intentional about the types of roles I took before I became CRO at Rocket Fuel to build out my chops as a go-to-market leader.

I wasn’t going to come up with CFO and I wasn’t smart enough to be the engineering leader. Again, that’s one of those things as you spike hard in one area and then you build horizontal experiences across the other functions. Maybe if you have a general manager opportunity to a large company. You can get to know some of the other functions but when you do that first CEO gig, how do you learn quickly?

Any last advice you want to share with our audience?

Underscoring what we are talking about before. If you’re a new CEO, I encourage you to make the time to invest in yourself and that means get a mentor and join a CEO Community. They could be valuable on many levels personally, spiritually, emotionally and then practically. They can help you, for example, figure out how to negotiate compact packages with the board.

In that specific example, you’ve never done it before. You don’t know what all the different levers you could pull and they have all the information. It’s total information asymmetry. If you have a group of people that only care about you and what you to be smart and learn from all their lessons that they’ve learned. It’s a wonderful way to share best practices and talk through scenarios. Build your tribe and don’t be afraid to ask for help. That’s probably the other thing as CEOs. Everyone’s turning to you for the right answer. Sometimes you say, “I don’t know. What do you think?” That will lead to great insights.

Episode Wrap-Up

Thanks for doing this. Its chronological foray through your career has worked.

My pleasure. I enjoyed it. I look forward to stay in touch.

—

I want to thank Randy for joining me to discuss his career beginnings, military service, work in tech, CEO roles and his slots on leadership and how to make the most of your career. He has had a very impressive career journey thus far. If you’d like to work on your own career journey, you can visit PathWise.io. You can become a member. Basic membership is free. You can also sign up on the website for the PathWise newsletter. Follow us on LinkedIn, Facebook, YouTube, Instagram and TikTok. Thanks.

Important Links

• Microsoft
• Salesforce
• Seismic
• Maxio
• McKinsey
• Execution
• The Chief Executive Operating System
• Entrepreneur’s Organization
• Designing Dynamic Organization
• Tony Zingale’s Linkedin profile
• YPO
• Vistage
• Alliance of CEOs
• Venwise
• Doug Winter
• Battery Ventures
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About Randy Wootton

Randy Wootton’s storied career includes military service in the US Navy, a variety of tech roles including at Microsoft, Salesforce, and Seismic, and three CEO gigs. He is currently the CEO of Maxio. With more than 2200+ customers, Maxio is the industry-leading billing and financial operations platform for B2B SaaS companies.

Randy is also active on several boards and with several charitable causes. He is a graduate of the US Naval Academy and also has an MBA from Harvard Business School.