Scale Like a CEO

From 9 to 90 Employees (and Back): A Founder's Journey Through Extreme Growth | Scale Like a CEO

• Justin Reinert • Season 1 • Episode 51

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What happens after the rocket ship stalls? We sit down with David Abbey, CEO and founder of Penny AI, to unpack the ride from pandemic-fueled hypergrowth to a bruising market reset—and the rebuild that followed. David shares how the team pivoted from an enterprise-focused AI CRM to Endlss, a polished influencer and affiliate marketing platform designed for founder-led D2C brands that need leverage, not overhead.

Together we dig into why influencer marketing is now marketing for small brands, and how generative AI can finally cut the manual grind: sourcing right-fit creators, personalizing outreach at scale, and tracking collaborations without drowning in spreadsheets. David explains the strategic switch from “ship fast” to “delight on first use,” why onboarding and opinionated workflows matter in a crowded SMB tool stack, and how tight ICP focus sharpened messaging and sales motion.

We also go behind the curtain on layoffs, survivor morale, and the culture shock of losing a major customer overnight. David walks through a transparent playbook—showing the books, briefing A players early, and resetting around fewer, higher-impact priorities—that helped the team stay aligned and deliver some of their best product quality ever. His leadership lens favors autonomy and trust: elevate the people you have, double down on strengths, and fill the gaps honestly. The closing takeaway is personal and practical: control your state. Whether it’s back-to-back VC pitches or tough customer news, the ability to reset your mindset may be the most valuable skill a founder can cultivate.

If this conversation sparked ideas for your own pivot or product strategy, follow and subscribe for more candid operator stories, and leave a quick review to help others find the show.

Speaker:

In this episode of Scale Like a CEO, host Justin sits down with David Abbey, CEO and founder of Penny AI Technologies. David shares his remarkable journey from rapidly scaling his team during the pandemic to navigating devastating industry challenges, downsizing significantly, and pivoting to Build Endless, a new product of the influencer marketing space.

Justin:

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

David:

Thanks, Justin. Yeah, pleasure. Damon Abby. I am the CEO and the founder of a company called Penny AI Technologies. And Penny is a company has two lines of business. Both play in the AI space. One was built in 2018 when AI was more machine learning and big data. And we built an intelligent CRM that effectively would automate the daily tasks of sales reps. The idea was to use company data, munge it all up, and then tell the sales reps what to do every day just to be more productive. And that business scaled to both 75 countries and 35 different languages. The second business is a new incarnation within the brand, it's called Endless. That works more in the influencer marketing space where the platform is effectively a workflow automation suite for small D2C brands looking to build and scale an influencer and affiliate marketing campaign. And that one is more around generative AI, around your messaging, around searching for the right types of influencers, and ultimately streamlining any small business with a small team's workflow.

Justin:

Great. And digging into that just a little bit more, you know, what problem does your company solve and why does that matter in the industry?

David:

For well, Tough and Endless, because that's the way we focus more on right now, is in the influencer marketing space, it's obviously become a dominant player where influencer marketing is no longer an octope. Influencer marketing is marketing. Big brands have lots of access to big budgets, big influencers, celebrities. Small brands don't. There's not a lot of technology available. That some of the technology that is is very expensive. So we've come in very specifically to target founder-led businesses, emerging D2C brands. Um, sub-50 million might be a nice umbrella, but our sweet spot is really sub-20 and even sub-10 million. And the idea being that our system can automate a lot of the workflow, a lot of the manual tasks that it takes a small brand to get their brand notice and get influencers talking about it so that their uh obviously month recurring revenue and the inbound traffic on their site picks up, their conversions rates picks up, the cost for clip goes down, the CPC goes down, uh, and just try to make them more efficient.

Justin:

That's great. I love any tools or platforms that can help enable or level the playing field for smaller businesses. I think that's great. So as you look at your evolution of growing Penny AI and then endless, what is one of the biggest shifts that you've had to make personally as shifted from co-founder to CEO and building the business?

David:

I have a bit of a unique story because Pen, the first product, when we launched in 2018, we were very fortunate with the time because when the pandemic hit, the the industry that we served, which was the direct sales, was booming, right? So we went from, I think when the pandemic first started and we all got locked up, we had nine employees. And when we got that a year and a half later, whenever we was allowed to go back outside, we had 90 employees, and I hadn't met most of them in person. So I had to go from scrappy founder to try to navigate a world that nobody knew how to navigate to figuring out how to scale a team. We we gentlemen called ourselves a virtual first company because I didn't meet people. And then in 2023 and 2024, that industry that Penny really served was heavily impacted to the point that it's almost kind of been wiped out. So then we actually had to downsize our team significantly. And in that process, I had to figure out what roles I had to give away, what roles I was wanting to let go of, what roles I didn't. And then when we downsized and ultimately built the new brand, I had to start picking up different pieces again. So I had to go back into the founder-led sales, I had to dive heavily back into some of the product, I had to dive heavily back into marketing. Where when we had that nice big uptick in 2021, 22, we had built teams and organizations, and we had 125 people to do all those things, and it was more oversight and working on business strategy. And then, of course, when the times changed, going right back down to the grassroots level and being involved in every sales phone call and every product meeting and every marketing meeting and writing email copy and conversion copy. And so I've run that whole gamut, and now I'm on my way back up, moving back into more of a CEO role, which is it's a wild experience.

Justin:

Yeah. So there's I'm sure there's got to be a lot of lessons learned that the second time around you are thinking about doing things differently. So if you think about the first time you scaled up and now scaling up again, what's something that you're consciously doing differently than the first time?

David:

Consciously a lot. The first one was the west in the sense where we were and we were scrappy, we were in a small organization going after monster enterprise brands. Now we're actually again a scrappier team, bitter than we were in the very beginning, of course. But we're going after D2C brands, and they are smaller by nature, and it's the relatability and it's the messaging and the focus, I think, on this one is a lot different because we know exactly who we want to talk to. We know exactly what their problem is. Whereas when our previous customers were multinational, multi-billion dollar publicly traded companies, they're huge. Right now, we just have to be laser focused to get to the right person at the right time. So, messaging, I think, on this one is one thing that we're very, very conscious about. And then the other one is because they are small brands and there's tons of competition in our space, building a product that is delightful. Whereas in the first one, we're like, hey, build scrappy, fail fast, it's okay if there's both. Let's just get out there as quickly as possible. Now it's like, no, we've got to build an incredibly polished product the first time out the door. So the first time someone uses it, they're like, wow. But we also have a team that's been working together for eight years that has all the skill sets to do that.

Justin:

Yeah. And so as you as you're growing, either the first time around or now, how do you identify and develop leaders from within the organization versus how many do you hire from the outside?

David:

Again, I've gonna have a bit of a unique point of view on this one because at our peak in 2023, we had 125 staff, and we had to do two rounds of layoffs and and downsize the team specifically significantly. And I remember I think it was the summer of 2024, we had a client that was worth a couple million dollars a year in revenue, and they just announced to the world that they're just shoving the door and their dove at the industry, and we had to let go of a large number of people. So the people that we have left on the team were were hand-picked to be there from a very large group of people that we had. Um super unfortunate situation to have to lay off people regardless. But everyone that we have on our team has been with us for years. I think we've added one new person, probably a year and a half. Um, and these are the best of the best, some of the best people I've ever worked with. So everybody has a lot of trust and everybody has a lot of autonomy because everybody's fighting a really good fight. So again, a bit of a different point of view. But if I look to hire, I don't need to right now because everybody is just working their ass off and they're in the trenches in a true startup.

Justin:

Yeah. Well, that's great that you you have this team that has been together for so long and seems to really work well together. And also interesting given that data, and I don't need to dig into it, but just data on engagement and how low engagement drops after layoffs, and it's even the most impacted are the most impacted are actually your top performers, are the most impacted as far as their engagement. I'm curious how you navigated that because I'm sure there was a pretty big hit. There's even, I've gone through it before myself of having kind of some of that survivor's guilt. Tell me a little bit about that and how you've gotten to this place where you're doing so well.

David:

Well, not easily. I remember speaking with one of our messages the first time we had to do it, and I was like, look, I have no idea how to do this. I've never done layoffs in my life. And he he gave us a lot of really great advice, and he's like, it's important to humanize it. He gave us this great thing. He's like, go to your A players and let them know it's coming and let them know why. Because what's gonna happen is when you go through a reduction in force, the team that is left is all gonna come into little groups and they're gonna chat. And your executive team is not gonna be invited to any one of those groups, and having your message echoed within that group is gonna be so important, and it's your eight players that are gonna be in that group. So we took his advice, and in each kind of department, we pulled in some of our A players and were like, look, this is the situation we're in, this is what the market is doing, this is very transparent. It showed them everything, why we got to this decision. This is why we're doing it. And sure enough, we made the announcement, we had to let go of a number of people, and those conversations happened, and those eight players were really able to then be like, Look, I know this sucks, but the reason the company did this is this and this and this, and it makes complete sense, and then it sucks, but this is where we're at. That was a strategy that we took. I mean, when our largest customer just turned off the tap, you know, if that was the day I put the tears and the blood, sweat, and tears, and I had to have an all-hands with the company, and I was like, look, this is not a decision that I made, this was a decision that was made for me, and I just had to be um honest and vulnerable. And I showed everybody the situation, I showed them the books, the cash, everything. But we just lost half of our revenue, which means we have to lose half the company. And in that one, we gave people the option that if anyone wants to volunteer before we make any festive kin. Um, and at the end of the day, it's like, well, it's this is just the situation we're in. And then it's just a matter of keeping the team focused and showing that there is a vision and there's a plan, and we're not just gonna wait to die, we're gonna keep fighting. And it's has not been easy at points, but it's always come out as best you can. And I have a friend of mine who recently had to do a layoff, and I gave him some not some opinions, but some experiences that I've had, and he ended up navigating it as best he can. It's it's a horrible situation. I don't wish it upon any employee, and I don't wish it upon any founder, but those are the trials and tribulations of definitely being a startup, but it happens in every line of business.

Justin:

Yeah, it can definitely be challenging. And I think your approach and being just super transparent is the only way to go if you want to keep the people that are all stick around engaged and trusting you to drive into the future.

David:

Yeah, that's it. So regardless of where you're at. You just raised a bunch of money, you're on your fine. Well, it's still a fight because you just promised someone else the world, and then of course, if you have to make the decision to do a layoff, that's that's hard too.

Justin:

Yeah, for sure. So, you know, it through all of these transitions, what's been the toughest part about maintaining alignment and culture as you've navigated kind of growth and expansion and and then shrinking and and then growth again?

David:

The incredible, incredibly challenging. We need to do less, but better. You just lost half your team. We have to do less, but we have to do it at a higher output. You've got you know, so say you got 60 people and you've got a roadmap for the next six months, and you've got marketing plans and sales plans and conference plans and travel plans and all these plans, and then all of a sudden you have half the team, but you just still want to accomplish all those goals, and you really start to get focused on what matters most, and you have to really hone in who you're serving, why you're serving them, how you're talking to them. Gone are the days when I had an eight-person marketing team who could do all sorts of cool stuff. Now we have a handful of people who do part-time marketing just within the organization, you just have to do it differently, and it is really hard. Uh, sometimes you find certain areas that output actually goes up. Everybody loves the less process and the less bureaucracy, but it doesn't mean that you're like it's easy. I'd say it's probably one of the hardest things. But if you do it, and right now I can honestly say that our engineering team is putting out product at such a consistent rate of some of the highest quality product I've seen in years. And it's a small, scrappy team. Um, and it is just really well thought out, really well polished. We know exactly what it's supposed to do. Um, and would I love to have another team? Absolutely. Would like to go faster, of course, but that's not what we have. So um yeah, it just takes it takes the the focus, and the focus is hard because everybody has competing priorities.

Justin:

For sure. And so, how do you define the leadership culture that you want to build as you move into the future?

David:

I think we take more of a democratic approach, I think, where we all want alignment across the organization. I obviously want to see certain things go, engineering wants to see some things go, product wants to see things go. Um I think when we were a very large organization, it was very challenging to get complete alignment across the organization because everybody was pulling in different ways. We had some customers that were so big it was kind of one of those scenarios where the tail wagged the dog sometimes, which made it even more challenging. Now, as a smaller team, um it's autonomy and trust, and just making sure we know exactly what we're all focused on allows us to be a little more flexible in that part. It's not a dictatorship any sense of me just coming in and being we're all pretty lined across the organization.

Justin:

Yeah, that's great. And what are you doing today to prepare for your next layer of leaders for continuing to build into the future?

David:

For the still organization of the business development organization, which is obviously where I spend the most of my time, is autonomy and feedback. I let people really find their own way and find their own voice, and just hey, have you thought about this? Have you thought about that? And just try to get them to broaden their horizon a little bit because yeah, the team I'm gonna have in place today, I don't want to hire a VP of sales, I want that team to elevate. That's always been my leadership style. I just try to hire really high-functioning individuals since I've hired some people who work great, I've heard some people that are spectacular, but you need people to really own their own. Uh, and once people kind of get in their groove, you can easily foster that and just kind of build them up a little bit along the way. And really, once you identify what they're good at, point them in that direction and then what they're bad at, try to augment them in any way you can. And that's been my leadership style. I am not a great copywriter, I love chat GPT because of that. But I knew very early on that I needed a marketer and I needed a copywriter, and I knew early on that I sought at the weeds, I do not like minutia detail. So my right-hand man is a guy who just loves the weeds, and you just gonna help people identify their weaknesses and let them know it's okay to have them, but let's fill those gaps as best as you can, and then you can really flourish at what you're really good at. Because if you love what you do and you're good at it, you'll you'll be excited to come to work every day.

Justin:

Yeah, that's great. And what is what's one piece of advice that you would give to another founder about scaling their business It's something that I known about before on LinkedIn, it's something I'm subscribed to.

David:

Um you have to be able to control your state of emotion and find ways to do it. And the best example you can ever give is if you go into a VC pitch and you get absolutely destroyed, and the VC tells you your idea is worthless and you're stupid, what are you doing? And you have another VC pitch immediately afterwards, if you can't control your state and get back to that, my idea is great, I'm such a strong believer, you will never be successful. If you go into that next meeting believing, taking it to heart with that guy just said, and you're not going to give this guy everything you have, you're gonna fail. But if you can control your state and not back and walk into that next meeting and crush it, whether that's a sales meeting, it's a new partner meeting, it's a client meeting, it's a VC meeting, it's a meeting with a lawyer, that is the most important thing you could ever do is control an emotional state. It's a 80% of it's in your head.

Justin:

Yeah, that emotional, I'm hearing emotional resiliency is so critical. That's yeah, for sure. Well, David, I've really enjoyed the conversation today. If folks want to get in touch with you, what is the best way to do so?

David:

That's the easiest way to find me.

Justin:

Great, great. Well, thank you so much for the time today, David.

David:

Absolutely, Justin. I appreciate you uh you having me.