Chris Combs of LinkSquares on the importance of getting the right people in the right seats

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In this episode, Elias Rubel is joined by Chris Combs. As SVP of Business Development, Chris is responsible for managing strategic partnerships and corporate relationships across the company.

Chris is a serial entrepreneur who has built multiple companies from concept. He brings a unique perspective on how to build and take products to market, while developing strategic relationships across prospects, customers, and partners.

Episode Outline

[04:39] Chris’s background

[07:16] What is takes to find product market fit

[10:13] What he learned was what success looked like

[11:18] Blueprint for entire future executive to impact

[12:04] Thinking about how a startup would scale

[14:34] Habits to be great at crossing the chasm

[16:35] Refuse to sort of sit and pontificate over like products and product

[17:04] How to find the right people and getting them in the right seats

[19:22] What was hugely valuable and formative for him

Chris' Inspirations

Advisory team at DraftKings and Carbonite

Connect with Chris



Elias Rubel (00:31):

So today, really excited to welcome. Chris comes to the show. Chris is a technology entrepreneur. I'm one of the founders of linked squares, which is a hyper-growth company right now in the contract space. He has over 10 years experience working in enterprise startups and has sold. He sold his first startup back. How many years ago was that Chris?

Chris Combs (00:53):

That's been probably 10 plus years ago now.

Elias Rubel (00:56):

Wow. Alright. So excited to have you on the show. Welcome. And I'd love to start digging into, you had this early success and you know, then 10 years later now you're onto your next big project and you're, you guys are starting to grow really quickly. So I'm curious, you know, what, what lessons were learned in that first company that are informing decisions that you've made along your current journey with link squares?

Chris Combs (01:22):

Yeah. it's definitely been you know, since I graduated college, I've been you know, working sort of at the intersection of technology and startups and, and have experienced a lot of different you know, successes and ups and downs and, and, you know, I think all important learnings along the way. You know, when we started that company was called you closer, started that around 2010 and worked on it for a few years and you know, had an awesome group of angel investors that we worked with. And ultimately, you know, didn't really find product market fit and, and ultimately, you know, got a handful of customers, but, but probably didn't double down on the things that were working best and sort of shedding the things that weren't working was probably one of my biggest takeaways and hindsight now was to, you know, keep, we should've continued to double down on the things that were working really well and, and you know, and so we kind of got spread thin and, and one of our largest customers was actually a big supporter of the company.

Chris Combs (02:42):

You know, had some their own plans with the platform. We were building around document management in the real estate space. And so you know, it kind of came down to it that what they wanted to do and, and what we sort of believed was the big opportunity where it's going be you know, two different. And so ultimately they ended up just acquiring the asset, the platform themselves, so they could continue to customize it for what they needed which kind of gave us an opportunity to return some capital and, and live to fight another day, as I say and, you know, it took away a lot of good learnings and it definitely was formative in you know, my future endeavors.

Speaker 1 (03:26):

So that's really interesting. I feel like a lot of the time there are these outcomes, just like you described that they can be so foundational even though they're not, you know, the classic Silicon Valley, like knock it out of the park, retire in your yacht type of story, but they can set the stage for future stories. Right. Like so how long did it take you, I'm curious, like, did, did you need to recover after that? I've talked to a lot of founders, myself included who you could go through some sort of an acquisition and it's exhausting and you've just grinded it out with this, you know, your baby basically where you ready to go right back at it right away, or what was that process like for you?

Chris Combs (04:16):

I don't know if I needed a break or rest, but I did end up taking some time to kind of figure out what I wanted to do next. I think ultimately the biggest step that I took was moving to a bigger market in Boston. You know, it was originally based in the Midwest and Louisville, Kentucky, and, and you know, sort of believe that I wanted to spend some more time in a larger market especially at tech market. And that was a big process. So ultimately kind of spent some time in San Francisco and, and with some friends and mentors there and, and you know, ultimately you know, had a chance trip to Boston where I knew some folks and, and you know, that was always, it was my, actually my first time going to Boston at the time.

Chris Combs (05:13):

And, and my first night in town, the Sox won the world series 2013. So that was my first night. Exactly. Yeah, that was my very first night in Boston. And so definitely kind of comm that combined with the folks that I knew and, and the fact that the company that I was you know, moving up there to work for was a company that I knew the founder of and you know, had a little bit of context, so I wasn't just coming in to the city completely cold. And so those couple of things were really helpful to, to sort of get over the hump. So, so that whole process of just like, kind of what we're both talking about, which is like a little bit of a reset after going through, you know, a startup took a little while, took a handful of months to kind of get going and then you know, sort of moved to Boston and got what I call my hands on MBA.

Chris Combs (06:17):

You know, I think for entrepreneurs, yes. Yeah. Got it. I think for entrepreneurs, it's, you know, it's, if you're really serious about being an entrepreneur, it's important to kind of spend some time at, at companies that are kind of in the later stages kind of B C round funded companies. Because the, the thing that I learned was what success looked like at that company. And having kind of done my first startup, I didn't really know what I was, what the phases and stages were. So I really, it was hard to kind of move it forward. But at Backupify was able to see kind of what a C round funded company of, you know, 75, a hundred folks looks like and the different departments, how they work together and what you know, how the whole combination of things sort of made it successful. And so having that point of reference and those data points was you know, very helpful for the next time that, you know, I sort of struck out and, and did another startup.

Speaker 1 (07:26):

And it sounds like, I mean, you met Michelle, your co founder at Backupify as well, right?

Chris Combs (07:31):

Yeah, we did. Yeah. So I'm almost all of the executive team at link squares. Now I previously worked with at Backupify. And Michelle was one of the first people I met there. And he invited me to a Patriots game. I been to a couple of NFL games before, but definitely told him that I had a bucket list for sports and you know, being in kind of a, a bigger city with proteins that some games I wanted to go to. So he took me to a Patriots game. And we kinda hit it off from there.

Speaker 1 (08:09):

Nice, nice. Yeah. So now that there are two reasons to join a later stage company one, see what the blueprint looks like to meet your entire future executive to him?

Chris Combs (08:20):

Yeah, no. I mean, and, and building that network of folks that you want to kind of work with in your future is, is important. And so I think yeah, I think those later stage companies there's enough going on that there's a lot to learn and there's also a lot of people to meet. So lots of benefits to that.

Speaker 1 (08:44):

Were there any things that you observed while you were there that were contrarian to your way of thinking about how a startup would scale, you know, like in your mind when you were running your first company and, you know, you had in your brain like, okay, this is what, this is what the next step looks like. This is what we need to do. And then you, you joined Backupify and you were just seeing it all play out, like was any of that different?

Chris Combs (09:12):

Yeah, I think that there was a ton of it that was contrarian and, and things that sort of cause me to rethink you know, how I've been building companies previously and the opportunity to really see experts like the executives on that team and see how they operated you know, it was really informative and also sort of, you know, grateful to have that opportunity. You know, I think that one of the biggest things was just that the aggressiveness with which the company operated on the sales front, on the marketing front you know, and seeing that you know, that the benefits to having a sales team that sort of doesn't take no for an answer is really pushing the envelope. And so seeing that, and then also seeing how they use that sort of aggressiveness to sort of position the company and a position of strength and as a company that, you know is really going places. And so, so I've sort of learned how to build that persona. And we built it really early on in link squares, and it really helped us get our first, you know, handful of early customers and early advisors and folks like that. So, so that was one of the things that stood out to me that, that I really leveraged my next time around.

Speaker 1 (10:52):

So let's, let's run with that because, you know, as you know, the point of this podcast is to focus on, you know, that post product market fit usually around a million and ARR where you go from your founders doing early selling, maybe an a E to, okay, we need to scale this thing and actually build out our sales muscle and our marketing muscle. It sounds like you saw a lot of theory and a lot of, you know, tactics that you can have now carried forward into link square. So walk, walk me through, like, walk us through some stories of what that looked like once you did have product market fit at link squares and how you've deployed some of those things that you learned at Backupify in actuality at link squares.

Chris Combs (11:36):

Yeah. I think that there there's a handful of, of things. One is just the, how you scale a structure and set up a team to scale. So you know, one of the things that I, we didn't really do, and it sort of goes back to, again, sort of a conservative approach is we didn't really hire you know, any sort of junior folks as part of our process to like transition and allow ourselves to, you know, focus on different tasks. And so that was one of the things that we did at link squares was you know, brought on some employees you know, probably earlier than it, we thought, you know, that there was definitely an argument. You said you could hold off or wait longer, but we went ahead and, and brought some folks on actually salespeople, which is kind of contrarian in itself.

Chris Combs (12:34):

Most folks would go hire engineers or other folks. We actually, you know, our first couple hires were sales folks, and that was because we sorta put the customer at the front. And we said like, if we can just focus on, you know, product market fit, figuring out who the buyer is, and, you know, really getting that buyer profile down to exact details and then having some people that can help us sort of, you know prospect and go out and find more of those because it's really you know, in the early days, you're really looking for those like early adopter folks where you might be able to find someone that fits your profile, but they're just not an early adopter. They don't really, you know, get excited about those early stages. They want to see products that are more developed and more defined, but there are also people that really enjoy sort of the early stage of helping define and, and do that.

Chris Combs (13:35):

So, so you're having to turn over more stones is that would say because, you know, the you're, you're just going to have to find more people to find those early adopters kind of on the what's the curve that I'm thinking of, I'm blanking on it the crossing the chasm type curve, right. You're, you're you know, you're trying to find that just first early group. And so you know, those were kind of the things where we we, we sort of push down that path and we're able to sort of form our first sort of reference customers and our first advisors to the company, which one of our crime it's to be an advisors that you also had to be a customer that you use the product every day. And so getting those first handful of folks that are really gonna back you and reference you and, you know, use your, you can use their logo and, you know, use quotes and put them on a reference call. Those things were super important and really laid a strong foundation. You know, so, so it was really th those were important pieces that we didn't really on the first time around. But having sort of seen success and seeing what, what really helped you know, that was important to kind of focus in on that in the early days.

Speaker 1 (15:02):

How did you make the decision that the time was right to bring in those hires? I know you said, you know, it felt like you might have brought them in earlier than some would have, but that you were happy with that decisions, or how did that thought process go

Chris Combs (15:18):

In some ways it's kind of a leap of faith because it, your, your instincts are probably telling you that it's too early. But if you don't do that and take some of those leaps along the way, then you're really not going to give yourself a chance to go work on other things. So like, you know, just having some earlier folks in to you know, help us prospect enabled me to go build relationships with the people that were sort of those early adopter types and really give time to listen and let them influence the product. And, you know, one of the other things that we did in the early days was we refuse to sort of sit and pontificate over like products and product features. We solely focused on hearing that from customers and then using the data we got from them to form the next features and decisions.

Chris Combs (16:15):

Because I think in the early days, it's really easy to kind of sit there and be, and say, be cool is if we did X or, you know, and you end up kind of, you end up kind of losing your North star, which is ultimately getting customers and getting people to use the product. And so we sort of said no to a lot of those things and you know, allowed those early hires to, you know, help supplement our efforts to talk to more customers, you know, and that was kind of our North star was just talking to customers as much as possible. So that helped accelerate that. And, you know they they've actually been able to kind of scale with the company as well. So it was neat to, it's been neat to you know, be able to work with them for as long as we have.

Speaker 1 (17:13):

That's really cool. Yeah. so now that you're in this scale phase where you're trying to get as much repeatability and build out your orgs, I'm curious, like, what is, what's your biggest challenge today?

Chris Combs (17:29):

You know, I think that it's definitely evolved you know, in my you know, the founders roles have evolved you know, and I think that's, you know, one of my takeaways, it's just you know, sort of allowing the company to grow and morph and, you know, build momentum on its own. And, and sometimes that means getting out of the way, sometimes that means taking on something, that's going to be a real challenge. Sometimes that means doing something you really don't, you're not that excited about but just kinda knowing where you can be most effective and, and you know how we can get the team in place to be able to be successful. So, so if I kind of had to think of the biggest challenge, it's really been, you know, finding the right people and you know, getting them in the right seats on the bus to, to continue to grow.

Chris Combs (18:30):

And again, I kind of go back to spending time at Backupify. We were able to see you know, sort of what how people performed in certain scenarios and, and then be able to call back on that, you know, at link squares and say like, okay, we know we need someone who's really good at process and organization of engineering teams. And to be able to say, okay, I know exactly someone who's, that's what they're an expert at, and then be able to go recruit them. And you know, you can imagine that that's a, that's a quite a challenge when you started back up and look at it from a bigger picture is identifications of where your weaknesses are which can be tough at times. And then assessment of, you know, what you need from a person, and then you actually got to go recruit them, convince them to quit the awesome job that they have and join your, your, you know, growing company, you know? And so you know, that's, that's one of the many challenges, you know, that we've, we've experienced. There's definitely no shortage. But it's, it's been rewarding too.

Speaker 1 (19:53):

So as we wind this down I always love to ask, you know, we, we have folks in our lives professionally who have been hugely influential mentors, or even peers, you would just look up to and think they do great work out there. Who are those folks for you?

Chris Combs (20:09):

Yeah, I mean, so, so many great ones to you know, reflect, you know, in reflecting on and, and you know, definitely sort of you know, my first group of angel investors were, you know, some really awesome folks that you know, sort of allowed me to believe that, you know, this is a career and a path that I could pursue successfully. So that confidence was, you know, in the early stages was, was really important. And then, you know the I knew a lot of the earlier at Backupify prior to actually joining the company. And so, you know, being able to kind of see them have success Rob Ben, Eric, a bunch of the early employees and then the opportunity to actually work with them in the later years of the company you know, was hugely valuable and formative for me obviously followed them up to Boston and saw the success they were having.

Chris Combs (21:18):

And so that put me in a bigger market with a bigger opportunity and sort of put me in a good position for the next thing I did. And then even at link squares you know, our advisory board from folks at DraftKings and Carbonite you know, companies like that you know, was really, you know, awesome to have them start backing us, especially in the earlier days when we weren't, we didn't have anything, everything put together at the time. But you know, to continue to sort of you know, be in our corner and help us along the way was, was really great. And, and they, you know you know, hopefully are enjoying some of the success that we've been having over the years and, and I'm sure it's been cool for them to kind of see it, see it come together. So

Speaker 1 (22:17):

That's definitely a lifecycle it's, it's it's fun to see these things evolve and to bring people along for that journey. So, Chris, thanks so much for joining us today. This was really, really an enjoyable conversation.

Chris Combs (22:29):

Thank you for having me.

Speaker 4 (22:36):