Scale Like a CEO

Scaling Startups with Sam Wehbe: Insights from a Veteran CEO | Scale Like a CEO

• Justin Reinert • Season 1 • Episode 34

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Growth shouldn’t feel like pushing a boulder uphill. We sit down with career startup operator and SignWell CEO Sam Wavey to unpack how a lean, bootstrapped team is beating heavyweight e‑signature incumbents by doing the opposite: simpler workflows, honest pricing, and enterprise‑grade security backed by fanatical customer support. Sam’s seen the startup journey from every seat—entry-level marketer to C‑suite across 30+ companies—and he shares a hard-earned playbook for scaling without the chaos.

We get specific about the moments that matter: how founders let go and shift from doing to leading, why A players attract more A players (and how to avoid the “bozo explosion”), and the traits that predict success when the road gets messy—coachability, empathy, work ethic, and above all, adaptability. Sam breaks down his “commander’s intent” management model, showing how clear goals and empowered teams create speed without micromanagement. He also contrasts VC-fueled hiring sprees with SignWell’s deliberate, data-led headcount planning that reduces layoffs and respects the real lives behind every role.

If you care about sustainable growth, this conversation is a blueprint. We touch on SOC 2 Type II, HIPAA, and GDPR readiness; practical ways to keep support obsessive; and the quiet advantages of leaders who live their values instead of posting them on a wall. The takeaway is simple and powerful: when product, channels, business model, culture, and leadership align, scaling feels like gravity working in your favor.

If this resonates, follow the show, share it with a founder who’s hiring, and leave a quick review—what’s one hiring filter you’ll tighten this week?

SPEAKER_01:

Welcome to Scale Like a CEO, the podcast where we dive into the strategies, challenges, and breakthroughs that define successful business growth. Today we have an incredible guest joining us. Sam Wavey is a career startup veteran who's worked with over 30 startups throughout his journey, wearing nearly every advocacy suite. Now, as CEO of Steinwell, he's revolutionizing the electronic signature space with a bootstrap approach that's outpacing many VC-backed competitors. We're going to explore what it really takes to scale a business, build exceptional teams, and lead with purpose in today's fast-moving startup landscape.

SPEAKER_02:

Dan, thank you so much for joining me on Scale like a CEO. To get us started, if you wouldn't mind, just give us a 90-second intro to you and your business.

SPEAKER_00:

Yeah, I'm Sam Weavy. I'm the CEO of Signwell. So from my perspective, I'm a career startup guy. I've worked with over 30 startups in my career. I've been the founder, I've been the entry-level person, and I've gone all the way up and done just about every role at the C level except for CTO. Okay. And Signwell, SignWell is a great little bootstrap startup that simplifies and automates document signing with legally binding electronic signatures that provide companies with enterprise grade security, record pricing, and compliance with like HIPAA and GDPR backed with just fanatical customer support. So that's that's us, myself and sign wrong and great.

SPEAKER_02:

And so what do you see as the biggest problem in your industry and how are you solving that?

SPEAKER_00:

Yeah, in the industry, I mean electronic signatures is such a nice industry. With a lot of the bigger companies, what they essentially do is lock customers into really expensive contracts and offer them really complex workflows, complex software. And we're solving all of that by just doing the opposite, offering a really cost-effective, cost-effective solution, as mentioned before, with enterprise grade security, we're stock two type two compliance, compliance with a full list of things out there like HIPAA and GDPR2. And there's just so many of them. And then we back it up with great customers towards. So generally, we're designed, especially from an ease of use perspective as well, for modern businesses. And I just find the older older gen out there are just offering complex, like the price value gap is just completely off for most customers. And that's what we're solving.

SPEAKER_02:

That's great. Well, now, Sam, I know that you have operated in that C-suite in many different companies in different different versions of the C. And so what I'd love to hear a little bit is as you have founded companies in the past and then begun to scale and hiring people, what are some of the challenges you faced as you started going from one or two employees to 10, 20, and beyond?

SPEAKER_00:

Yeah, I think I've been a founder and I've worked with tons of founders. And I think generally it's going from the person that tries to do everything or is trying to do everything, to hiring the right people that can put in the right processes and systems to help you scale. And I think that transition, if you think of crossing the chasm, well, it's crossing the chasm, not for products, but actually for people. And I think along the way, a lot of founders do struggle letting that go, letting go of the instinct to do every simple thing, to you're really hiring the right people that can do all that for you.

SPEAKER_02:

Yeah, and that's that's a very what I hear a lot is getting the right people on board. And so uh over your tenure in different companies, and you think about that size of company, kind of scaling company from anywhere from two to 30, 40, 50 employees, what are some of the qualities that you've found make a good fit for someone?

SPEAKER_00:

Yep. So number one, I go for a players, and I know people say this all the time, but I believe, and this was coined by Guy Kawasaki, and I believe he was quoting Steve Jobs, but A players bring A players and B players bring C players who bring D players, right? And then they coin that as the bozo explosion. So number one, I'm always looking for A players because I believe that once you bring A players, they will then start bringing more A players and you build a really strong company that way. That being said, and I don't want to sound like an egomaniac when I say this, but I'm looking for folks that have my qualities, right? You know, I'm someone that started off at the entry level. I was an entry-level marketing person, and it grew to the C suite. And so one of the things that was I was extremely coachable, right? I knew what I didn't know and teach me. I was hungry for success. I knew I wanted to be in the C suite. I knew I wanted to be a leader, I was empathetic, I really knew how to work well with people. Intelligence was important, but I think the other thing that people really need to look out for is cover work ethic. There's a great article by Malcolm Godwell, and he's quite known, right? It started off as an article in the New Yorker called David and Goliath, and then it became a book. But essentially, it just states that work ethic trumps intelligence any time of the day. And that was really my motto I wasn't always going to be the smartest person in the room, but nobody was going to outwarf me. And so generally, I'm looking for that in people. And the other thing I'm looking for, especially because we're in the startup game, and startups are crazy. They're absolutely nuts. There's a great book out there called The Messy Nettle by Scott Nelske. Got a great image on the cover. You start off here, then you scribble the line, and then so people that survive at startups and thrive at startups are adaptable people. So they say it's not the strongest that will survive out of a startup, it's the most adaptable that will survive in a startup. And so I'm looking for people, it doesn't matter if they're in the middle of their career, later in their career, or early in their career, that can tell me stories about having to adapt, right? And I tell people, well, I started in marketing, then moved to sales, then I moved to product management, then I then I moved to customers like fast, and then so I moved around, I've needed in startups that they kind of end and flow through their life cycle. And I'm looking for that in those type of people. And I think once I do find those people, what I do is I keep them, I take them with me everywhere I go. So if you come to a startup and I've hired you and you're an eight player, chances are I'm gonna take you to the next startup. And if you tell me, Justin, you tell me, hey, I work with these five amazing eight players, I will go out of my way to try to talk to them. And if I think that they're as good as you say they are, then I will put them on my bench. And I go to companies with a deep bench of eight players and I bring them on board. So that's the thing that I try to tell folks is eight players are hard to find. When you find them, you keep in touch with them, even with DV, you I've had a player get offered better titles, more money. I will stay in touch with them because at some point our class will cross again, and and and and keeping that deep bench will benefit me and the company I'm at.

SPEAKER_02:

Yeah, that adaptability, I think, is so key in a growing company because there's just so many things that that can be thrown at you that you need to be able to adjust and adapt to those things. So so understanding, I think you give a lot of great examples of what an A player is, and I've definitely heard that multiple times of A-players hiring or bringing in A players. Um how do we know when it's time to add people? So I think that's also another challenge is getting it right of how do you how do you build the team and add people to the team without you know sinking the business and try and spending too much money, right? There's a delicate balance there. I'm curious how you've navigated that.

SPEAKER_00:

Yeah, it it's a really tough thing. I went to a startup um where I was probably employee number 50. And you know, within 15 months, we had gone from seed to series B. We raised over 81 million dollars from Bessemer and Insight partners and some really big VCs. And we ballooned to about 150, 160. Oh, and that was really challenging because we we had sold the store and we had to we had to staff up to make sure that we could keep up with our growth rate. You know, we're growing 100% year over year. And if you're gonna get to a B, you have to get to a C within a certain time frame. I think a lot of companies fall into that trap and sometimes overhire without real data behind them. Signwell is a bootstrap startup. So when we hire, we hire on purpose. And and so we sit down, Ruben and I, who's the founder of Signwell, and we say, okay, what is it we want to accomplish in 2026? And what is it we want to accomplish in 2027 with respect to 2026? We say, okay, this is what we want to do from a revenue perspective. This is what we want to do from a technological perspective, a human perspective. Now, what do we need to execute on that? And then we start to break it down by department, okay. And we start making trade-offs because startups are inherently a huge extra, multiple exercises in third off. And we come down to where we think we're going to have the most impact, okay, and then we hire and according to them. So if we believe partnerships is big next year and it's going to drive the most impact for us, then we will stop accordingly in that sense. And so what you have with Bootstrap startups is more purposeful hiring, less layouts. And I think generally that's the right way to approach things. But what we're getting now is almost like a Wild West mentality where AI is a great example of that, where everyone's just trying to bring on as many developers as they can to work on AI solutions. And when it's not panning out, you're seeing mass layoffs, mass layouts, mass layoffs. So generally partnering with purpose in accordance to realistic plans is really the best way to move forward.

SPEAKER_02:

I really like this idea of intentionality and purpose in thinking about how you're scaling the business and bringing people on, because it, I think for some folks, it's it's easy to forget that when you're bringing people on to a company, you're also impacting people's lives. And so you do that too fast and irresponsibly, that you're irresponsibly spending money in the company, then you're also when you lay off, you're impacting people's lives in doing that. And so I really like the intentionality and purpose in how you look to build the team so that you're being responsible for the business as well as being responsible with other people. I really like that. When when you add to the team and you're growing, you inevitably then start to build in layers where you need new managers to be able to be leading people. How do you approach that when you're growing organically and then growing your leadership within the organization? How have you approached that in the past or even today?

SPEAKER_00:

Yeah, my management philosophy is called commander's intent. Okay. And generally, what it what's involved in that is setting clear goals, giving general direction, but empowering your people to make changes in the day-to-day because hey, life comes at you fast, right? And you have to people can't just be waiting around for you to say yes or no to things. If you've hired the really good people that we just talked about, uh, and you've coached them and taught them to think like you and reason like you, then they should be able to make decisions like you. And so generally, that's the way I've always worked. We sit down, and I mentioned this earlier, and say, well, what is it we want to accomplish next year? Here's our North Star. Usually it's five, right? It's your revenue goal, your financial goal, your human goal, your technological goal, right? And then you start to break that down by department, and then you start to break that down by functions, and then you set your metrics and so on. So it's a waterfall effect, but everybody's aligned. And so if you've hired the right people and give them the right direction and empowered them, that's generally how things work in really great stuff. And that's that's how I mentioned earlier that one company we went from one million to double-digit millions very, very quickly and raised a ton of money just by employing that philosophy. It was actually COO and CRO of that company. So I want to say in terms of how to set direction, but also then running the revenue side of the business and the operation side of the business to achieve it. And we absolutely killed it over a few years and had a blast doing it.

SPEAKER_02:

Incredible. So, what does the future look like at Sinewell?

SPEAKER_00:

We're growing, and I think generally we're growing faster than I think a lot of VC backed companies. I think we're doing so because you know it's being run by two gentlemen who have been there and done that, right? Ruben's a two-time founder. Um, obviously, both companies are still operating and doing well. I've passed the 30 startup market in my career. So we essentially know what we're doing, but we also lead by example. And I think that's a really important part of being a leader and building the right culture. I think generally it's easy to pay lip service to whatever values you throw up on a website. But if your day-to-day behavior contradicts all of that in front of your employees, then how do you expect them to be those values, right? So I think generally we put our money where our mouth is. We are expressive customer support. If we're thrown sat for customer support, I don't have a problem spending the whole day in customer support. I get to talk to customers. Well, I don't want great introductions. I want a great CSAT score on obsessive that I want those scores. And that's the example that I'm setting for my employees, right? And Boobin's the saying hey, the executives don't have a problem getting rolling up their sleeves and really getting and working in the business. And so kind of the way we work. So we are growing because we live our values, we have our fundamentals really right in the sense that we're solving a real problem. I can't tell you how many startups don't do that, right? We have a great product and does it. We have channels are set, we know exactly how to go to get our business model is fantastic, whether it's a SaaS or volume based on the API side. So our forfeits are there, our culture is there, leadership there, employees are there. And you know, and this is what I told someone the other day. When you get you get it all right, it's like pulling a boulder down a hill. It's so easy. But if you don't have those fundamentals in place, it's like pushing a boulder up a hill. And I can tell you, most people get run over by that boulder, right? So that's kind of what's in store for us. We're just we're just doing really, really well knocking wood, and just feel like 2026 is is always to be another great year for us.

SPEAKER_02:

That's amazing, Sam. If folks want to get in touch with you, what's the best way to do that? Do that?

SPEAKER_00:

You can find me on LinkedIn. If you mention signwell, you'll you'll find me there, or you can visit our website at signwall.com. And either way, I'll be happy to chat.

SPEAKER_02:

Great. Thank you so much, Sam.

SPEAKER_00:

Thanks.