Hitting aggressive growth goals, transitioning from a large company to a startup, and narrowing your focus with Chris Ritchie (Managing Partner at Integrity Power Search)

Chris Ritchie 00:00
It was honestly probably the most stressful year of my life, because we had very aggressive sales goals that needed to be hit, and we needed to hit those for fundraising reasons and other reasons as well. We had some really good early traction. But when you take on investment, you have to perform and deliver incredible results in a short amount of time.

Callan Harrington 00:22
You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Today's guest, we've got Chris Ritchie. I'm really excited for this one. Chris is the Managing Partner at Integrity Power Surge. Chris, welcome to the show.

Chris Ritchie 00:50
Hey, Callan. Thanks for having me.

Callan Harrington 00:52:
Excited. So tell us a little bit more—what is Integrity Power Surge, and what are you doing for them?

Chris Ritchie 00:57
So IPS has been around since 2012. We're essentially a full-stack recruiting firm specifically for technology companies. That mostly involves venture capital-backed technology startups and PE-backed technology companies as well. We're full-stack, meaning that we work across various different roles. So we do everything from full-stack software engineers to product management at the IC, manager, and director levels. We also do a lot of go-to-market roles—a lot of account executives, growth marketers, heads of talent, heads of finance. And we also have an executive search practice that does VP-level and above technical and non-technical roles. So pretty much, we want to be the all-stop for anyone at an early-stage technology company that needs to build their team.

Callan Harrington 01:40
I think that's interesting too, that you guys are doing also the go-to-market side, because that's a real need in the marketplace. There's tons that are on the engineering side—those are great firms, right? And I think that they're very necessary, but I don't see as much there, and I know that's a big pain point in the industry. So there's a lot of things I want to get to, and I know one of the big ones is—we'll get to this. We'll come back to this. But you made a switch from executive COO level at a startup, at a product company, at a tech company, to jumping over to the services side. You're probably one of the people that I've seen who's one of the most passionate about actually helping put people in the right positions. And I'm not just saying that because you're on the show. I just remember thinking, "Man, this guy really, really likes doing that," which is really cool, which I want to come back to. But before we get there, where did this all start? Where did your career kind of kick off?

Chris Ritchie 02:35
Yeah, so I went to Miami University in Ohio and studied finance. You know, I honestly don't even know why I picked finance, outside of maybe just knowing that I loved business and I wasn't sure what I wanted to do, but I thought that finance would give me the most flexibility, right? It's like, okay, go and learn finance. If it's not for you, maybe you can get into sales eventually, like some of my other family members who are all in sales. And then, you know, I interned at Abbott Labs, and they're one of the companies, like GE and several others, that have a professional development program. So it was four six-month rotations within finance in your first two years. And I was like, "Perfect, I don't know what I want to do. This is an opportunity to get to travel around and do a bunch of different jobs and see what I like." So I spent about four years at Abbott, the first two in that development program. I ended up rolling off that program and started in finance full-time at a company, and realized that it wasn't for me. So I ended up kind of moving over to the retail sales organization and moving to Seattle to help support the Costco account at the time. I got to use numbers and analytics, but also got to be more in front of a client, in more of a client-facing role. So I really enjoyed that. I have nothing but good things to say about Abbott. I just think, for me, I realized that big corporate America just was not the right fit for me.

Callan Harrington 03:53
Yeah, I didn't realize that you were there for four years, so you gave it a real shot.

Chris Ritchie 04:07
Oh yeah.

Callan Harrington 04:07
I'm actually always curious about this because I always was super intrigued by the rotational programs. So what all different aspects did you see in that rotational program?

Chris Ritchie 04:07
Yeah, so this was finance-specific, finance and accounting-specific. I did six months in Chicago, where I supported—at the time, it's now AbbVie, but there was one consolidated company at the time at Abbott, and it was like the branded pharmaceutical division. So I supported, specifically, more of an FPA role, but I supported South America, Latin America specifically, for the branded pharmaceutical side. So there was a lot of country roll-up and preparing financials for the executive team to look at, just to monitor the health of the business. That was my first six months. I was in Chicago, and then I went to Columbus, and I ended up doing cost accounting at the manufacturing plant downtown. So complete opposite—going from Chicago to wearing steel-toed boots and safety goggles walking around the plant. Really, my job there was to prepare a weekly report that showed how efficient the plant was running. What was our fill time? How much downtime did we have on our lines? Did we reproduce what we needed to? How much waste did we have? It was building that weekly report that the plant manager could look at and see what's going well, what's not, what do we need to adjust? Really cool, different perspective and way different work. It was fascinating.

Callan Harrington 05:18
And you moved this into more of kind of a client-facing account management role. What was that transition like for you?

Chris Ritchie 05:26
It's interesting because all throughout high school and college, I was in the service industry. I think naturally, before I got into that, I was actually pretty shy around people that I didn't know. But working as a busboy at a restaurant in town, La Tavola, and then going into college and working at different restaurants as a waiter really kind of prepared me to have to figure out how to build quick rapport with different people I didn't know. I think I kind of missed that. I was more internal-facing in finance and accounting, right? You're interfacing with internal folks and helping them, but you're not really more outward, external-facing. I really enjoyed that aspect, where there was travel, trying to find mutual win-wins in the business. For us, it was all about how do we work on programs that will benefit both Costco members, Costco, and ourselves? It was a really interesting business because at Costco, it's all about how do you maintain the distribution you have? Because one product, one SKU line, could be $80 to $100 million of revenue across 350 Costcos at the time. They could just say tomorrow, "We're going to rip this out, we're going to put your competitor's product in," and you could lose that revenue overnight with a national decision. So it's all about how do you maintain distribution? How do you show value? How do you drive programs to add value to the member at the time? It was a really interesting use of my math and Excel skills to build models and dig into this, but then how do we use that in a way that could benefit externally? I thought that was a really cool, interesting piece that I didn't necessarily have before.

Callan Harrington 06:57
You hit on a couple of things. One, it's kind of funny how often it comes up—those original, those kind of first jobs, right? Restaurant jobs, retail jobs, different things like that. People bring up all the time how much that influenced later parts of their career. I think a lot of times we almost overlook those, but we don't realize how much they actually do have a downstream impact. And two, I think that finance background helps from a sales perspective, especially when you're doing cost justifications, business cases, and enterprise sales. Being able to actually demonstrate that ROI is a pretty big value add. Did you find that to be the case?

Chris Ritchie 07:36
Oh, 100%. Not only did it help me there, but when I transitioned more into the startup world. I didn't initially start in sales, right? Eventually, that was the last stop I had at my first startup spot that I was at for four years. But it especially helped not only work on an ROI story for enterprise sales but also for sales leadership. Especially in SaaS, you have to be able to explain and build a model. You're given a target for a company for a certain amount of time, and it's on you to figure out, "How do you build a model in which you're going to achieve this?" It's a baseline of, "Okay, how many leads do we need to present? How do you build a funnel to talk through that story?" But also a build-up from a team perspective—building a financial model so you can hit the unit economics that you need to, accounting for ramp time and all of that. So it's heavy Excel use. It's heavy modeling and figuring out what makes sense—when do I need to hire this rep? What type of quota, what type of team quota attainment do I want to bake into this goal? I just feel like, especially nowadays, you can't just be the salesy person who swings and shoots from the hip. You need to be able to explain things through data, study it, and build a model and really show that to make sure that your assumptions are in a good spot.

Callan Harrington 08:46
I think it's a great point, and it was a point that I was not good at early in my career. I was very much culture. I was a good recruiter, and I understood the mechanics of sales pretty well, and that just basically got me by, but then I got punched in the face a few times by like, "Hey, Calen, we really need this report, and this has to be accurate." I want to talk about—so you were in a sales role, or sales account management role, at Abbott.

Chris Ritchie 09:16
This was like a sales support role. You know, I didn't have complete ownership over an account. I was kind of like their super analyst, but got to take on some of those sales responsibilities over time.

Callan Harrington 09:25
Okay, so you were able to kind of dip your foot in the water, but still doing a lot of kind of that modeling in the background. Is that right?

Chris Ritchie 09:30
Correct.

Callan Harrington 09:31
Okay, was it from Abbott that you went to your first startup?

Chris Ritchie 09:36
Yes.

Callan Harrington 09:36
What was that like?

Chris Ritchie 09:37
Stressful.

Callan Harrington 09:38
How come?

Chris Ritchie 09:39
For many different reasons. Honestly, I’d love to touch on this later around stuff that you just advise people on, or maybe some keys to success. But a lot of it, I owe to my friend Travis Hedge. I was the corporate America person, you know, going through that, but something didn’t feel right. I was used to changing jobs every six months and having so much change, and then to kind of come off that and have this career path laid out for you—it just felt like, you know, people progress at different rates. It didn’t feel like I ever had the true opportunity to fail. So I wanted an opportunity to really sink or swim, right? Like, what am I made of? You know, I’m young. Bet on myself. Let’s see what happens. Worst case scenario, I could always maybe find another corporate America job if it doesn’t work out for me. But, you know, I really didn’t have any exposure to that world until Travis and I talked about it, and he heard everything I was saying. He’s like, "Well, you should look at a startup." I was like, "Well, what’s that?" So I started to break into it, and I started having conversations. You know, I was living in Seattle at the time, and I was talking to some companies in the Bay Area, and then I got connected to this company in Columbus, you know, my hometown. I didn’t even know that there were tech startups in Columbus at the time. I had various conversations, and I ended up getting a job offer when I was in town for work, actually, and decided to take it. I went back to Seattle, packed up whatever I could fit in my Mazda 6, and drove five days cross-country. Left everything else in my condo that I was renting at the time. Still, some of that stuff still exists there today. I have some friends that live in that house. I came back and moved in with my parents and started that following Sunday. 40% pay cut, no equity. It’s a different world when you go from being a low-to-mid-level member of a team of 10 that’s part of a broader organization of a couple hundred people to being the only finance and accounting person at a company. I remember hearing, "Hey, you know more about finance and accounting than anyone here, so you’ll probably pretty much figure it out. Don’t bring your company down," was the message. That was scary for me to hear at 25 years old. A couple panic attacks later, it was definitely a big adjustment.

Callan Harrington 11:46
Travis, great guy. Travis is the CRO at Vouch and has done a lot for Columbus, not even living here. He’s done a lot for kind of building Columbus out, so definitely a shout-out to Travis. So you’re in here, you’ve got the position, you took a pay cut, went across the country, you were clearly bought into what was going on and really just into startups in general. How did you figure it out? How did you navigate it once you were in there? What was that like?

Chris Ritchie 12:15
You know, it’s different, right? When you’re in a corporate job, most likely, someone had that job before you. So you have training manuals that are built out and a process that’s maybe 90% done—your job is to take that 90% process and make it perfect, keep the train on the tracks, let things run. Oftentimes, you have cross-training, and there, it’s like there was no one to train me, really. This is what needs to be done, let’s figure it out. Everyone’s working at 100 miles an hour, and they have their own work that needs to get done. A lot of it is self-learning, and a lot of it was Googling, honestly—"What does this mean?" or "How do I do this?" or "What’s the right way to do this?" That was a huge adjustment for me, and I think it created a lot of anxiety upfront because a lot of the stuff I did early on, I wasn’t sure if it was exactly right, because it’s such a different world, doing something that’s already been done and iterating it versus being v1 on a lot of different stuff. So yeah, I think it was just a lot of self-experimentation and self-learning and figuring it out, to be honest.

Callan Harrington 13:17
Did you find that you liked that challenge, that that kind of drove you more than having more of a defined career path, or did you not like it at first, and it took you some time to kind of get there?

Chris Ritchie 13:32
I think at first, I actually did not like it, but I also didn’t have a ton of confidence in myself. I’d never really done anything like that before, and I think it was more the fear of failing that drove me to figure it out, versus really anything else. But I think it was by going through that experience that it gave me the confidence to be more comfortable with risk and try new things that I ended up really liking that—having to figure out new things that I haven’t done before, or later on, how that silo that I owned works with sales, and the impact of that, and other things that I really learned to like over time. So I truly think it was that experience of not saying that I was exceptional at it, but just being able to figure it out and get things done well enough for what needed to be done at the time that really gave me the confidence to want to take on even more risk over time, take on more responsibility, and try new things. But at first, I definitely did not like it, and it was something I just had to push myself through.

Callan Harrington 14:30
Yeah. Startups, I’ve found in my experience that you face—and I’m not saying this was you, but it was in my career heavily—I had imposter syndrome at every single step.

Chris Ritchie 14:39
Totally.

Callan Harrington 14:40
At every single time, I’m like, "Man, I think they’ve got the wrong person." And then you turn something in, or something would happen, and they’d say, "Wow, this is great," and it’s like, "Nice." So I felt, I know what you’re saying on that. It is those—it’s almost finding those small wins that give you the confidence to say, "Okay, I am the right person." Then you push yourself a little bit more, and then you get out of there, and then you push yourself again, and you just kind of keep building that confidence. Is that essentially what you’re saying?

Chris Ritchie 15:09
Yeah, I mean, I don’t think it was imposter syndrome in that moment in time, but I do and have felt that in pretty much every other role since then. I think it would just be hard for anyone to come into that role. I think it’s just, early-stage startups are really hard. You have to be someone that is intrinsically motivated, can do a lot of self-research and trial by error, and figure things out. I think that for people that are like that and love that open canvas and can be an owner and really drive, I think it’s an amazing opportunity, for sure. I think at first, I feel like I am that way, but it was such an adjustment because my last four years were like, "Do these defined processes and tasks," right? These things that were built up, so I was almost kind of conditioned and used to that. So I think it was just a wider adjustment for me, but once I made that adjustment, I think it really empowered me and propelled me a lot in the several different roles I’ve had since then.

Callan Harrington 16:06
That makes sense. I think you figure out pretty quickly whether or not you like this environment, and quickly, relatively—it could be two weeks, it could be six months, it could be two years. So I think that’s excellent. So you were in finance. How did your role kind of evolve at that company?

Chris Ritchie 16:21
Yeah, so I came in as finance and accounting hire number one, pretty much. I think I was around employee 30. I was in that role, I believe, for about a year, year and a half, and then we raised our Series C at the time, and I got to hire an accounting manager underneath me with a CPA, which was fantastic because I had taken some accounting classes, but by no means am I a CPA. So that made me feel a lot better. Then about six months into that, we did a reorg, and I went from having me and, I think, one or two people underneath me, owning the finance and accounting function, to then owning several other organizations that just support the broader company, right? So, HR, talent, sales operations, facilities, finance, and accounting. It was kind of more of a broad administrative officer-type role, and I think I had a team of 14 at the time, so that was a big jump, especially from a management leadership perspective, to go from that and then learn these new areas at the time. I was really only in that role for about six months, and then the CEO, Sean, asked me to be his chief of staff. Originally, I kept my team and supported him, but I realized that he was on the road probably 70, 80, 90% of the time, and I had to be with him on that. It’s hard to have a team, so my team ended up getting dispersed. I wasn’t really an owner of anything at that time. My job was to help support Sean in whatever he needed done and help communicate that through the organization. So it was a lot around fundraising, some recruiting—like executive search-type things, early sales of the Olive product were the other things that were the three big things that I helped him with. But that was also an interesting transition, to go from driving something to being in a chief of staff role, where your job is to communicate and get these strategic initiatives through. So I was in that role for about a year, and then I came in and led—I was Head of Sales my last year or so that I was there, during that initial sprint when we grew the sales team out quite a bit, had some really good commercial traction. So that was the last stop that I had before I ended up leaving Olive.

Callan Harrington 18:24
What was that transition like for you, from having a team of 14—a good-sized team with multiple departments and functions within there—to moving from that to more of a chief of staff role? What was that like for you, personally?

Chris Ritchie 18:37
I loved it. Honestly, Chief of Staff is such a special role because you get to be in rooms where there’s no way you would have normally been in that room. Being able to talk, interface in Silicon Valley with some of the top investors, and just being a part of that conversation—even if you’re just taking notes and not participating—just the fact that you get to listen and see how decisions are being made, whether it’s selling or whatever that may be. I think I gained a ton of empathy and respect for not only Sean, but all startup CEOs. I didn’t think I truly realized how hard of a job and how stressful of a job that Founder CEO role is until I was in a chief of staff position. I think everyone can sit back and say, "Oh, if I was CEO, I would have made this decision, blah, blah, blah," and that’s easy if you’re not in the room and don’t see what these people actually go through. It’s an incredibly demanding and stressful job. I think that was something that really was my biggest takeaway.

Callan Harrington 19:35
I have to assume you could learn just an absolute ton in that role.

Chris Ritchie 19:39
Absolutely.

Callan Harrington 19:40
So then you transition from there to leading the sales team. Much like your Abbott transition, you were on that finance side, led a lot of that—not exactly apples to apples—but now you’re jumping back on the sales side. What led to that decision, and what was that like in general?

Chris Ritchie 19:57
I’m honestly not sure exactly how it happened, to be honest. I think it was a mix of just helping Sean on the sales side with some of the big partnerships we were trying to work on at the time, and really enjoying it. I don’t exactly remember how it happened, but I ended up taking a very small team, and we grew it a ton. How we kind of devised it was, health systems were our main vertical that we were selling after, and so it was like building a sales team to go after health systems. Then I was kind of like a player-coach, where I had my own quota and I went and sold and managed the pipeline for non-traditional verticals. Fresenius Medical Care would be one; kidney dialysis centers would be a non-traditional example. Services organizations or others that weren’t particularly health systems could be companies that I would interface with and actually sell to myself. The reality of the situation was, I didn’t have a track record in selling, so it was important for me to go out and be able to sell, to be able to help advise the team on what’s working as well. So it was a very collaborative environment. It was honestly probably the most stressful year of my life, because we had very aggressive sales goals that needed to be hit, and we needed to hit those for fundraising reasons and other reasons as well. We had some really good early traction. But when you take on investment, you have to perform and deliver incredible results in a short amount of time. So I think for me, to be in a role that was so new that I had never really, truly done before, mixed with a very new technology as well, and the pressure of what needed to happen from a performance perspective—it was incredibly, incredibly stressful but rewarding at the same time.

Callan Harrington 21:43
I can only imagine, especially since you guys were Series C, Series D at this point, is that right?

Chris Ritchie 21:49
Yeah, so I think from a funding round perspective, it was around Series D, but from a product maturation perspective, we were probably a little bit earlier than that, because there were a lot of other startups, a lot of pivots that happened in trying to find product-market fit before that. But it was an example where the company had to perform and had to bring really good sales results in a quick timeframe.

Callan Harrington 22:11
You mentioned that it was rewarding. What was the rewarding part about that?

Chris Ritchie 22:15
I think just having a team to rally behind a goal. I’d say that’s the biggest thing—being able to make quarters. When you’re in the trenches with the team and you have a big goal, and it’s like, "We need to figure this out," and it works. Whether it’s luck or skill or probably a mix of both that occurred, I think that’s always rewarding when a team rallies behind a goal and is able to achieve it. I was out of my lane completely. Thankfully, I was actually working with a coach at the time—his name’s Chris McAllister. He really helped keep me sane during that time period as well, because, again, I’m someone who really—I don’t think I had failed professionally at that point at all, and the stakes were even higher. I really just did not want to fail. I really wanted to do what I was tasked to do, and we were going to figure this out and go. But I think he really helped me through that phase and helped me try to bring my best self. Because, again, sales was new. Leading a team was new. When I had my team, I quickly kind of gave up my team when I was Chief of Staff, and then I was back to owning a team and then growing a team. Now I had a massive team compared to what I had, right? So it was just a lot of new elements for me and how my brain works. It was all about just putting things in perspective and doing your best, and the team rallying behind a goal and being able to accomplish that was incredibly rewarding.

Callan Harrington 23:36
I love that. So you were very successful in your time at Olive. Where did you go after Olive?

Chris Ritchie 23:43
Yeah, so I ended up transitioning out of Olive when the team was pretty big, and it felt like, at that point, I didn’t feel like I was the best person suited to lead that sales team anymore. They needed to bring in someone who was really good and had been there, done that—a sales leader to take them to that next level. I really wanted to go—I had done all these different roles, and for me, it was like, how can I leverage? I don’t want to specialize in one specific role. How can I leverage all my experiences and maybe go earlier stage and take on a bigger role where I can own more functional areas, especially because I know how they all interact? So that was the goal. I ended up taking three months off just to relax again. It was a very kind of stressful ride. I wanted to take some time to myself, spend a lot of time just journaling and figuring out where I wanted to go next, and what levers were the most important to me. So I started talking to early-stage companies, and there just wasn’t the right opportunity, role, or company at the time. So I actually ended up joining IPS for a little bit, more specifically helping the founder, Caleb, with VC partnerships, helping him get in front of more VCs, telling our story—it’s a big referral engine for us. But I also did some executive search work when I was there as well. So I was an IC recruiter, and that was my first time really doing recruiting. I had a very small stint overseeing talent at Olive, but I didn’t do any recruiting, and ended up bringing Olive on as a client at the time and helping hire a lot of the sales team members for that team once I had left. That was awesome, and I was really enjoying that work. But then I got the call where it was like, "Okay, this is the role, this is the company." So I ended up joining as COO at Finite State. It’s another Drive Capital company in town. I met Matt, the CEO. I really liked Matt, but I think what really stood out for me was the role was exactly as the COO supporting a first-time technical CEO. I had ownership over everything besides product and engineering, really, so I got to oversee the roles that I individually had done or led at Olive, which was really attractive to me. But I think it was the mission that really stood out to me the most. It seemed like a need-to-have product, not a nice-to-have product. The product is the ability to reverse engineer critical infrastructure to be able to see what’s inside of it, what the weak points are, and how a bad actor could take advantage to either take control of the device or use it as an entry point to move laterally on the network. Think everything from consumer-grade items like you and I interact with—a Roku or Smart TV or Ring camera—but also on the industrial side. This is connected car infotainment systems, critical components in substations of utilities that power our grid, to 5G equipment that powers our cellular networks. Matt and the team believed that this was going to be the new biggest attack vector that people would start to go after. So to create a company that could give you visibility into that and bring you actionable insight so that you can get ahead of it to lower the likelihood of an event occurring really spoke to me. It was almost like the ability to help protect the country, in a way. So I really was attracted to that, so I ended up joining that team in December of ’19.

Callan Harrington 26:56
So you took some time off, journaled. What was your process for journaling?

Chris Ritchie 27:01
There was a mix of just stream of consciousness—whatever’s on my mind. There’s also a series called Wait, but Why?—I don’t know if you’re familiar with that. There were some really good prompts involved there, so I used some of those prompts. And then I also just had some conversations with people that I really respected, that I knew were really intentional, self-aware people. I tried to see, "Hey, have you gone through something similar? What have you done?" I talked to Travis; Andy Sparks is another person who I talked to quite a bit, just to get some ideas from him on how he thinks about it. So it was really kind of breaking down—sometimes I’d just write whatever’s on the page, and sometimes, if I really wanted a question answered, I would write the question and see what comes to mind and try to unpack that deeper and deeper through that process.

Callan Harrington 27:50
I think it’s one of the most impactful things I’ve ever done. In particular, I’ve done both of what you’re talking about—if you’ve got something you’re really stewing on, but then you stream of consciousness that stream of conscious journaling. That’s exactly what I did when I went through my career transition before starting my own company. That’s kind of what came out of that. I found that, for me, the first month was just getting everything out of my head. I had so much stuff in my head, I couldn’t even get to the real stuff until that was all cleared out. Then I saw things much more clearly—what do I actually enjoy doing? All those different types of things. So you went through this process, and from that process, you took some time off, continued to do that, and then got the job that you wanted. You got in the position that you wanted. You’re with the mission that you wanted, the team that you wanted. What was that like, and what were some of the challenges that came in that position? Because now you’re at an early-stage company, in an executive role, got everything that you wanted. What was that like?

Chris Ritchie 28:52
A lot of it was new, but the one thing that was common at the time when I joined was it was really a pre-revenue company. At the time, the main vertical they were selling into was healthcare. So I was like, "All right, healthcare, owning all these areas at once—that’s new, cybersecurity, that’s new—but at least there’s healthcare." Then I think a month or two into the job, we shut down selling to healthcare. It was not the right place to sell into for the product at the time. I was like, "Okay, everything’s just going to be new." Honestly, I think that I felt more stress when I joined Olive, just owning the finance and accounting side, than I did at the time, even though the vertical was new in cybersecurity, we were selling into new verticals that I’d never had any experience in, and I had all these areas in a bigger role. It was just gaining some confidence and being in the uncertainty that I felt more comfortable. I guess I wasn’t really comfortable, but just less stressed than I was maybe when I first joined, because I had that experience before. But it was awesome. It was a lot of digging into trying to find product-market fit. Okay, here’s the problem we’re solving, here are all the different areas. What ended up happening was we ended up paring the product down a little bit and just focusing on really the secret sauce. The product was doing two or three things, and there were other companies in the market that were doing just one thing that was becoming more of a commodity at the time. So we made the decision, "We have a finite amount of—no pun intended—finite amount of resources, engineering resources. Let’s trim this product down from doing these three things to this one thing that we believe we’re best in the world at," which is more of the reverse engineering piece. Because originally we were monitoring these devices on networks and doing all this stuff. I think it was like, "Let’s do this one thing we do really well, and let’s find the vertical in which these people feel it the hardest, that they would pay the money to be able to bring this product in." That was a really cool experience, to be a part of that product-market fit journey, go help land the first couple early adopter customers, and then be able to build the use case sales material and go and hit the market from there. So that was a really cool experience.

Callan Harrington 31:02
I think that’s such an important lesson. It’s hard when you’re an early—especially pre-revenue, right—early-stage company. It’s so hard not to be opportunistic. "Hey, we can do this. This company wants this. We’ve got a great client. They’re paying us X for this product." We’re building all products for all people, and we’re going after all sorts of different customers. But then you hear this a million times, right? Everyone’s like, "Start with a niche, then expand." But it’s hard to not be opportunistic in those early stages. This is VC- and bootstrapped. Oh yeah. I think that’s such good advice on finding your niche. Where do you solve the biggest pain that’s differentiated from those that are around you? This is anything—this is even somebody looking for a job. Where are you uniquely fit, where you are going to be the best, you’re going to have the best negotiating power, you’re going to be able to pick more of those companies? Now, it’s going to be totally different if you want to do something different, I totally get that. But almost anything—niching down first, because you can always expand later. So I think that’s excellent advice.

Chris Ritchie 32:04
I think with that too, right, I think the biggest challenge being at that early stage is not finding the people that say yes to you. It’s the ability for you to say no to people. When you’re early on, you’re grinding, you’re scrapping by. It’s easy when you find a customer, but they have a unique pain point, and they’re like, "Well, build me this or change your product to do this, and we’ll give you a $100,000 contract." It’s really hard to turn that down. But in reality, that could be some unique situation for them, because they have this tech stack that doesn’t solve for this, and it’s more of a custom development product where maybe you can’t really productize that and then go sell that to the market. So the ability to dig in and be like, "Does this customer have a pain point that others really feel? And can I productize this, or am I just building something custom for them?" That’s what I think is probably the hardest thing—you can’t solve everyone’s problems with the resources that you have. You have to solve the problem that the most people really care about. That’s repeatable at the same time, and I think that’s the hardest thing.

Callan Harrington 33:10
I think that’s excellent. So what I’m really curious about is—and I know that you talk a lot about this—you were on the tech side, you got everything that you wanted, and then you went back to IPS as a managing partner. What drove that? What was inside you that you just had to do?

Chris Ritchie 33:25
It’s interesting. I think there are a lot of different reasons. I think, first, why leave Finite State? Matt and I had a conversation early on that was more like, "Hey, listen, cybersecurity is very new to me. This is all very new. I feel good about helping you at these early stages, getting things off the ground. Let’s find some product-market fit. Let’s get the customers, let’s raise some capital, let’s build the team." But they’ll probably reach a point, like at Olive, where it will require people that really have a different stage fit than I have, per se, and have that singular scaling experience that I don’t necessarily have. That could happen in a year; it could happen in four years, we don’t know, but we had kind of a mutual agreement upfront. I think we just hit that timeline faster than at least I expected. I think it really started around raising the $30 million Series B last year—I think that just escalated timelines, at least from my perspective, where it was like, "Okay, with this money, we need to deliver even more revenue, but we have the capital to bring in really amazing people and leadership." At the time, I felt like I had sold enough, but again, selling a technical product to a technical buyer is such a different ballgame than selling a technical product to a business buyer or non-technical buyer. The type of questions that you get asked, the type of things that they care about—it’s completely different. Even though I was selling a technical product at Olive, I was not selling to a technical buyer, and that was a variance that I didn’t even think of until I was actually in the seat and experienced that. So for me, it was time. We got revenue in a good place, we got a v1 commercial team, but it was time to bring in that excellent VP of Sales to come in who has cyber-specific domain experience, experience selling into this persona, and can take that team to the next level. Same thing with a General Counsel and Marketing and Talent and Finance and all those different areas that I felt like I was good at a lot of things, but not excellent at that one thing. It was time to bring in really good people at that time. So yeah, I helped bring in those people. I had a really good strategic exit from the business. I either wanted to start my own firm, or I had this opportunity at IPS to join specifically to run the executive search practice and the go-to-market and operations practice—the below VP-level, non-technical roles. So why search? Everything changed at both companies when we elevated who we hired to not hire who was convenient, but really being intentional and putting resources behind finding the right people that we needed to—that truly changed everything. I mean, I’ve been a part of companies that have thrown out entire code bases and had a product. Your company is not your product. Your company is your team, and that is your best asset. I was like, if I could help companies at the stages that I’ve been at, maybe avoid some of the mistakes that I’ve made, and maybe be able to double down on some of the good things that I did during that time, that would give me a lot of value and passion. I spent a lot of my time just helping Series A, seed-stage founders. Let’s talk about hiring your first couple sales reps or your VP of Engineering. Let’s talk about it, and being able to lead a team focused on delivery and finding the right person and seeing these companies that do extremely well. But it’s also rare in life to find a situation where it’s a win-win-win. I’ve had situations where we placed a CTO at a Series A company, and the CTO is just like, "This is my dream job. Thank you so much." The executive team is just fired up, and the investors are fired up. Everyone feels like they’ve won because they found that perfect fit. That’s a really awesome feeling to chase, and it definitely picks you up from the low points in search because it is a rollercoaster. But yeah, that’s why I wanted to get into search—how can we help these founders who are really passionate about what they’re building, but help advise them in some of the biggest decisions they’re going to make, which is who’s on the team and who should be on the team?

Callan Harrington 37:14
So you were driven. It was really that fulfillment. Is that fair to say? Even hearing you talk about this, I can see you light up. You get super excited as you’re talking about it. I remember having the conversations together when you were talking about some of these things as well, and I just remember you always kind of came back to this. Is that what it was? Was it more of like, "I want to do what gives me the most energy"?

Chris Ritchie 37:36
Yeah, I think a lot of it was energy-driven, for sure. I think a lot of it too, was to be so laser-focused on one company and be all-in on one problem, right? Olive for four years, Finite State for two years—it was kind of nice to get into a perspective of how can I still be in the technology startup scene, but come at it from a different perspective, where I’m more of an advisor versus operating and doing, but also have exposure to a lot more investors, a lot more founders, and learn new industries. I’ve gotten to interface with Web3 crypto companies and VR/AR and insurtech and deep AI/ML—areas that I’ve maybe not had much experience in at all, but I get to meet those founders and learn about their businesses, and that gives me a lot of energy as well. So yeah, I’d say it’s definitely the energy of helping these founders make the right talent moves, but also the exposure of being able to have access to a lot of different people and industries and all of that gives me a lot of energy as well.

Callan Harrington 38:37
Gotcha. So that exposure to all sorts of different challenges, people, and things like that is a big driver in that for you?

Chris Ritchie 38:46
Oh, totally. It’s more of an art than a science, right? Every founding team has a different DNA, skill set, and experience level. Each company is different. Is it a very technical product that needs a lot of resources? Is it not? Is it more marketing-heavy than technical? Each organization looks different. It’s hard to say, "Here’s your exact playbook." I think because of that dynamic, it’s such an interesting problem-solving space where no day is the same.

Callan Harrington 39:13
I love that. I think it’s kind of a perfect segue to the question I always ask, and this could be at any age period, but if you could have a conversation with your younger self and give them advice, what would that be?

Chris Ritchie 39:26
A couple of different things. The first thing is just simply, always keep your fixed costs low and avoid big lifestyle creep. So I’m a huge fan of, when you’re making your work decisions, being able to chase—if it’s passion or having ultimate flexibility—I’m a huge believer in keeping your fixed costs low to give yourself the most optionality and flexibility to make decisions, right? Being in a circumstance where you can quit your job and take another job for 40% less because you want to optimize for the learning experience, the responsibility that maybe you’d have to wait 10 years at your current company to get. But if your finances are all out of whack and you can’t afford to do that—I know it’s not fair to say and apply a one-size-fits-all because people have different responsibilities, but when you can keep your fixed costs low to give yourself the most optionality and flexibility to go chase what you want to, that would be the biggest thing, especially early in your career when you can optimize more for experience versus money upfront, because that eventually—if that’s what you want—could help lead to that down the road by giving you the ability to get into rooms you maybe couldn’t, or into roles that maybe you couldn’t before. I’d say the other thing that comes to mind is surround yourself with the people you admire and can learn from. Again, I don’t think I would have ever worked at a tech startup if I hadn’t known Travis Hedge. I don’t think it was innately built in me that this was maybe what I was supposed to do. I think it’s something that someone taught me, and I admired Travis and what he was doing with his career. I was like, "Hey, let me learn a bit more about that." It was like, "Okay, this sounds amazing." So I think surrounding yourself with people that support you, challenge you, and push you is always great. Let’s say that you want to break into a startup, but no one you know is in a startup, or you want to learn more about it. One of the coolest tools out there right now that wasn’t around when I was 21 years old is Twitter. I think Twitter is such an interesting way to—even if you’re not participating—get in the room with people that you wouldn’t really have normal access to and just learn from. What are they reading? What are they saying? What are their engagements? That’s fascinating. If you’re curious about, let’s say you’re a big tech product manager, but you’re interested in a startup—there are all these early-stage product managers that post a lot of great content and give their thoughts on things, and you can engage with them. Being able to use technology to allow you the opportunity to learn from people in that sense, to give you that ability and that network, is really cool. So I’d just say use technology to your advantage as well.

Callan Harrington 41:58
I 100% agree with both of those. You’ve given us so many good things today. Chris, thank you for coming on the show. This has been excellent.

Chris Ritchie 42:08
Awesome. Thank you very much for having me.