Engineering Leadership Series - Derrick Franco
Welcome to today’s interview. We’ve got a truly insightful guest with us. Derrick Franco, the Director of Engineering at Counterpart joins us to discuss his journey. Derrick is someone whose perspective has been shaped by jumping into the startup world at the young age of 15. He’s spent years navigating challenges and building innovative solutions as well as launching a podcast and book project.
Throughout the interview, Derrick shares his unique perspectives, experiences, and valuable insights. Whether you're interested in the future of work, leadership, or how technology is reshaping industries, you’re in for a treat.
Enjoy the interview and give Derrick a follow.
More Information
https://derrickfranco.com/
https://www.linkedin.com/in/derrickfranco/
https://yourcounterpart.com/
https://creators.spotify.com/pod/show/fowproject
https://www.instagram.com/the_future_in_progress/
The Interview
DoneStreet
Tell us a little about your story. How did you discover your interest in software engineering. How you got to where you are today?
Derrick
Yeah, great question. Growing up, I always loved technology and computers. It started as a curiosity, just clicking around, seeing what things did and why. I knew I wanted to do something with computers, but I wasn’t sure exactly what. It felt like a never-ending loop of curiosity and every time I figured something out, it led to more questions. That sense of discovery kept me hooked and always kept my attention.
By the time I was around 12, I started learning to code, making small websites and experimenting. Then, at about 15, I began working with my first startup. From there, everything just snowballed. That’s how it all got started.
DoneStreet
Sounds like you got started at a pretty early age. I guess you’re a little bit of a prodigy they might say.
Derrick
It was really about scratching that itch. My uncle was involved with a company that needed a junior programmer, and since I was already into programming, he asked if I wanted to give it a try. I was around 15, so I jumped in. They had a couple of other engineers, and I just started experimenting with things. Early on, I realized how much I enjoyed the tech and startup environment, which ended up shaping a lot of my early career
DoneStreet
Were you in school and doing it part-time concurrently or how did that work?
Derrick
Yeah, at the time, I was in Michigan, and we had just moved to Connecticut. The company was based in San Diego, so I started working remotely before the tools were really set up for that. I’d fly to San Diego during the summer for longer stretches, but mostly, I was working from home. That’s how it all began, and things just snowballed from there.
DoneStreet
That's very cool. You’ve created a podcast as well. You created and host the Future of Work Project Podcast. It's a program dedicated to bringing together smart and thoughtful leaders. Curious, how did you come up with the idea? What inspired you to start the podcast?
Derrick
Ironically, the idea started in 2019, around the same time I was just getting started with Counterpart, the company I'm with now. One of the key things Tanner, our CEO, and I agreed on was that investing in great people and treating them well would create a strong company culture. A great culture leads to long-term success. I’d seen this firsthand at other companies, both in places with great cultures and, for lack of a better term, terrible ones. The difference was clear.
Not only did you see it in how people worked together, but also in how well they worked. This got me really curious. I wanted to dig deeper and see if this theory true. Was this just a bias from my past experiences, or was there something to it? The idea was twofold: to explore this and to push forward ideas I’d seen work at other companies. Remote work hadn't really taken off yet, but I had built a small technical team remotely and worked remotely myself. I saw the benefits and how powerful and flexible it could be.
I also saw the importance of investing in your people, and that’s when I thought, “Okay, I can learn more and help others adopt these practices.” That’s how it all began. I recorded the first couple of podcast episodes in late 2019, planned to launch in 2020, and released the first few episodes just as the world shut down. Suddenly, everything I had been advocating for, remote work, flexibility, and new ways of working, became a global experiment.
The podcast naturally evolved with that shift. Instead of just talking about theories, it turned into exploring what people were actually trying. The whole world was experimenting, especially in 2020 and 2021, and I wanted to capture that. Originally, I planned to write a book on the future of work, using the podcast as a public-facing platform for interviews. But with Covid, the focus changed. It became less about what the future could look like and more about what people were actually doing and experimenting with right now. That’s really where the podcast took off, especially during that period. About 20 episodes were recorded during those years.
DoneStreet
Thinking back to the conversations you've had, is there anything in particular that is very memorable or that you learned from speaking with multiple people?
Derrick
Great question. Honestly, I think every single person that I interviewed, there was something that I took away, something that made me think, "I’ve got to try that" or that just clicked with what we were doing at the time. But there are definitely two or three interviews that stand out because of the timing. I spoke to two remote work experts, Chris Herd, who started First Base (which I think was recently acquired), and Darren Murph. If you’ve followed remote work over the past few years, you’ve probably heard of them.
Both were big advocates of remote work and active across social media platforms, sharing their expertise. For me, it was incredible to talk to them because it really confirmed a lot of what we were already doing at Counterpart. We were building a fully remote company, and hearing their perspectives, especially at different scales, was eye-opening. At the time, our team was still growing slowly, and mostly based in the Americas. In North and South America, while they were working with teams across the globe, from California to Dublin and even further east. It was just great to see those different dynamics in action.
Another interview that stands out was with Aaron Dignan, who had worked on several startups and also did consulting to help companies scale and adapt. When I interviewed him, Counterpart was going through a period of rapid growth where we had almost doubled in size and we were experiencing a lot of growing pains. His insights were spot on and felt like they directly applied to what we were going through at the time. It was almost like the conversation was tailored to exactly what I needed to hear for what I was going on the day-to-day as well.
DoneStreet
Counterpart, you've been there for six years or so. How did you join the team there?
Derrick
It’s kind of funny. As I mentioned, my background is mostly in small businesses and startups, where I’ve specialized in early-stage growth. Things like getting an idea off the ground, building the first team, and securing that first round of funding. I’d say I really specialize in that zero to 10 or zero to 15-person timeframe. I was at another startup as a founding engineer, and at the time, I was struggling with the direction the company was taking. Ironically, I’d been reaching out to people I knew for advice.
While I was doing that on LinkedIn, Tanner, our CEO, messaged me. He had just moved to L.A. and wanted to connect with someone in the area. It turned out he was the co-founder of a company called Button, which I knew from a mutual friend in New York. Tanner and his co-founder had run it for about five or six years, and it’s still going strong today. At the time, Tanner had just left Button to move back to L.A., so it was a perfect connection. I mentioned that I knew his co-founder, Chris, and Tanner said, “Yeah, great guy.”
So that’s how we originally connected. I met with Tanner to get his advice on the situation I was going through, but also just to meet someone in the area. It was a dual purpose. Getting advice from someone who’d been through similar challenges, and also hearing about an idea Tanner was working on. He definitely planted the seed. As it became clearer that I wasn’t going to align with where my company was headed, I started getting more curious about what Tanner was doing. The rest is history.
The running joke is that Tanner might be one of the sneakiest recruiters I’ve ever seen. He’s done it to a lot of us. He just shows up where you are, and it feels like a coincidence until you really think back and realize, “Wait, were you really at that coffee shop just a block and a half from my office in San Francisco that one weekend, or did you actually fly up here?” It’s funny now, but it always makes me laugh.
DoneStreet
Yeah, that's pretty funny. Some genius 4D chess there.
Derrick
It really is. It really is. And, yeah, it keeps working to this day, for sure.
DoneStreet
As a founder, that’s kind of the role you're always playing. Trying to bring on the best people continually.
Counterpart is an insurance platform that leverages AI management for professional liability coverage for small businesses. Is that correct? Is it using AI to do risk assessments and how exactly does that work. What is the problem that you are solving that the market was missing?
Derrick
Yeah, so it all started with the problem we were trying to solve: creating more trusting and less risky work environments. Going back to what I mentioned earlier about the future of work, we were focused on improving environments and building better company cultures. That’s where we realized the same theory applied, that companies investing in their people tend to have better cultures and are less risky. That insight became the foundation of Counterpart.
We knew that we had to align incentives. Simply telling a bad boss to “treat your people right” isn’t going to change anything. The initial idea was, what if we could make it tangible? What if we could show that companies who treat their employees poorly are riskier? That they pay higher premiums every year for insurance because of claims, lawsuits, etc.? If we could gather that data and make it visible, we could then offer solutions like HR services, and other tools. The idea was that by reducing risk for the company, we’d also be improving outcomes for the employees, which benefits everyone in the long run. That’s how it started, but we’ve taken it much further since then.
To answer your question, the systems and data we have now allow us to get a full picture of a company beyond just the application they submit. We’ve also built our systems to help our underwriters provide better service to customers. It all comes down to putting the customer and people first, which is a core tenet at Counterpart.
For our clients, whether they’re the policyholder, the company, or the brokers we work with, our risk engineers can work with them in ways that other companies can’t, thanks to the technology we’ve built. They can make changes much faster because of the AI-powered systems we’ve implemented. Our underwriters have access to data quickly, and our APIs are just speeding everything up. We’re continuously integrating this technology, so the systems learn from each other and improve over time. That’s really what we’re doing.
It’s been working for a while now. We use data to give us a complete picture, whether it’s from a system perspective or what the system provides to our underwriters. The result is faster and better decision-making all around.
DoneStreet
That's a really cool and unique idea. It basically sounds like you want to get a really good feel for the culture of the company to help make informed decisions on their risk for potential lawsuits or things like that. And then you also take a bunch of other data from within the company to really run the numbers and calculate where the risk is. Then you share that with underwriters who develop policies based on that.
Derrick
Correct, exactly. The more we do, the smarter our systems get. We have tools that help with things like assessing risk, speeding up our underwriters’ workflow, or automating some of the tasks they handle for simpler accounts. It’s part of a cycle where the system learns from every account, even the more complex ones, and gets better over time. So, while we might not use the system for the toughest accounts right now, it can still learn from them and then handle simpler cases much faster.
We’re not just letting the AI handle everything, though. We take a more thoughtful, methodical approach to how we use it. A friend of mine who worked in AI for years once told me that his biggest concern with the release of LLMs (large language models) was that companies might face lawsuits if they just let AI run wild. So, we’re definitely careful.
The goal is to set up the AI system so underwriters don’t have to touch as many things and can get tasks out the door quicker, while still keeping everything under control.
DoneStreet
How do you gather data from the companies? Is it data that they manually submit to you or is your software embedded?
Derrick
We continue to pull things in from our system and as they interact with counterpart more, we get more data internally to learn what they're doing. It's a nice cycle that we have going on to build the systems.
DoneStreet
It sounds like through these metrics you might end up with novel sets of data that the underwriters have not seen before. Is there a sales pitch on your side to sell this new dataset to the underwriter?
Derrick
It all comes down to understanding workflows, especially in insurance. It’s an interesting industry, similar to finance, where relationships play a huge role. Just because data says something doesn’t mean it accounts for the human element. For example, I could present data to an underwriter thinking it’s exactly what they need, but they might consider their personal relationship with the broker, which influences their risk assessment. They may filter the data through that lens, even if the numbers suggest a medium risk.
The key is not just showing the score but understanding how they want to see and use the data. Information overload can make data useless and too much noise and people start ignoring it. It's like being subscribed to 50 Slack or Teams channels and only checking the top 3. Important messages in the others get ignored because there’s just too much coming in. So, the challenge is providing the right data in a way that’s useful for the person executing on it.
DoneStreet
You touched on LLMs a little bit earlier. Are are there any other AI technologies that you're excited about today or that you’re looking forward to using in the future?
Derrick
Personally, I lean more toward Claude and Anthropic for LLMs. Their models are performing really well right now. What we’ve been focusing on is helping non-technical team members learn how to use these tools. At first, people without a tech background can be nervous and unsure how to interact with them. But once they get comfortable, the results are amazing. So I’m excited about that and bringing non-technical people into using these tools day-to-day.
I’m also excited about the growing use of datasets. For example, Google’s lidar data for self-driving cars is huge. It's a massive resource that can be applied in many ways. Like, lidar can map out roads affected by forest fires in LA and help model 3D maps of areas to navigate around. The more data we gather, the more we can adapt it for other systems, which is exciting for AI.
On top of that, we’re seeing companies realize they need a lot of power for these AI systems. As a proponent of nuclear energy, I think this push could lead to more companies exploring small or modular nuclear reactors. This could drive a cleaner grid over time, though it’ll be a slow shift. Still, it’s possible we could see cleaner energy as a byproduct of all this AI development.
DoneStreet
As an engineering leader, how are you approaching hiring? Especially on the remote side, how are you strategizing and hiring?
Derrick
For us, the cultural fit is big. We’ve been remote from day one, even before Covid, and we hire talent from all over the world. What we really look for is someone who is not only talented but also extremely curious. Our team thrives because everyone is eager to learn and collaborate. I’ve worked with people in the past who wanted to be the top dog, but that’s not what we’re after. We want people who are curious, want to work with smart colleagues, and are true team players.
That mindset is why we've had such low turnover over six years. We prioritize cultural fit, curiosity, and hiring people who challenge us. If I’m bringing someone in, I want them to be better than me. I'm looking and asking “Are they a cultural fit? Are they curious and are they better than me?” That's literally what I've been doing. We’re looking to raise the bar every single time we hire.
If you’re the smartest person in the room and you’re not hiring right, you’re doing it wrong.
DoneStreet
It sounds like a good way to summarize it is “Be curious, be humble and be driven. And maybe a 10x engineer every once in a while is a pretty nice hire.
Derrick
Exactly. On the 10x side, people often burn out because they’re expected to do everything without support. They get thrown into the fire and told to figure it out, which leads to burnout and turnover. It all starts with having a clear way of working together and making sure the culture aligns with the person. Without that, it’s not going to work.
There have been times when we’ve passed on talented people because they didn’t fit the culture. Even if they were skilled, if someone sensed they might clash with the team or had an ego, we didn’t move forward. We’re not looking for people who come in, disrupt, and leave short-term gains at the expense of long-term problems. Building the right culture means balancing those factors carefully.
DoneStreet
For sure. I think that's an underrated fact that you brought up about burnout which often leads to turnover.
It sounds like you've put a lot of thought into this. How do you generally approaching leadership. What makes someone a good leader in your eyes? And are there certain things you try to do and certain things you try to avoid?
Derrick
For me, it’s all about putting my team first. I always say my job is to make their job easier. Sure, I hire smart people who can solve problems on their own, but if I’m just handing them a problem and saying, "Good luck," I’m not doing my job. I need to provide the context, and story of why we’re doing this. To help them understand the purpose, and remove any blockers to keep things moving forward. If they don’t feel aligned with me, it sets us up for failure.
The more you show you’re willing to put in the work to support them, the more they’ll speak up when they need help. You’re creating a safe space where they feel comfortable bringing problems to you. Even if they don’t need you to solve it, just knowing they can talk to you makes a huge difference. If they feel you’re not in it with them, just barking orders, the results won’t be the same. It’s not about being hands-on in every project, but knowing your team has your back when things go wrong opens up so many possibilities.
DoneStreet
You've undertaken a lot of entrepreneurial endeavors in your past. Even from starting at such a young age of 15. Are there some key lessons that you learned early on that you carry with yourself today? And what are some of the secrets you think to being successful, things that you would want to tell your younger self.
Derrick
Great question. No real secrets per se, but for me, it’s all about passion and curiosity. If you’re genuinely curious about something and dive into it, your passion will carry you forward. You never know where those paths will lead. But the most important thing is starting. Even if you don’t feel fully prepared, you have to begin and see what happens. Some projects will fail, things won’t go right, but you have to take those risks to improve.
Looking back, I did a lot of things just to see what would happen, and sometimes it didn’t work out. Everybody feels like you’ve got all the eyes on you at all times. The truth is, people aren’t watching you as closely as you think. If you mess up, it’s not the end of the world, just move on and keep going. Good things come after that.
DoneStreet
Yeah, I think that's really sound advice. Even thinking back from my own personal past experience, it’s definitely something that has been useful to try and apply. Just take action and don't get caught inertia.
Derrick
Yeah, yeah, exactly.
DoneStreet
When you're older, let's say you're 80 years old, looking back, what do you want to have accomplished in life?
Derrick
You know, that’s a great question. If I look back, I’d be happy if I kept learning and pursuing the goals that truly sparked my curiosity. The podcast is a perfect example, and I’m even rewriting my book now as I learn more. Whether it takes 2, 5, or 10 years to finish, just knowing I’m working toward those things would make me feel fulfilled professionally.
On a personal level, if I can look back and say I was a great husband and father, and we lived the life we wanted, I’d be extremely happy. There's a quote from Conan O'Brien, I’m probably butchering it, but he said something like, “If you do what you love with people you love, it’s the definition of heaven on earth.” That really resonates with me when I think about all of this.
DoneStreet
Yeah, that's awesome. And I think very succinct and very humbling in a way.
Derrick
Yeah, it definitely changes over time too. If you’d asked 18 or 21-year-old me, the answers would’ve been very different. But as I’ve gone through this, I’ve learned it’s a marathon, not a sprint. Sure, there are moments when you need to hunker down and push hard, but if you keep going without pacing yourself, you’ll burn out. It’s all about knowing how to sustain the long run and enjoy the journey along the way.
DoneStreet
Yeah for sure, I think that's some more solid advice. Where can we send people to follow your work and updates, both personally, professionally?
Derrick
I’ve been building in the background for about two years, especially as I’ve been rethinking the Future of Work project. The name is actually changing to *Future in Progress*. You can find the Instagram handle @the_future_in_progress. The content will start rolling out later this year. I’ve been taking a step back, focusing more on writing and research first, and now I’m shifting gears to share content once the book and everything else come together more.
DoneStreet
Maybe we could dive more into the updated version of the podcast?
Derrick
Originally, the Future of Work project was focused on questions like: What is the future of work? How are people adapting? What new ways can we work, and how can we improve? I started writing the book and doing interviews, but when Covid hit, it became clear by the end of 2021 that everything was an experiment. Some ideas I thought were 10 years out accelerated quickly due to the pandemic. We’re still seeing the effects today. Whether it’s with commercial real estate, people being called back to offices, or issues like quiet firing and layoffs.
At first, I was writing a book based on theory, but I quickly realized that no one could confirm what was going to happen because we were still 3 to 5 years away from seeing real change. So, I paused, reevaluated, and started thinking more deeply about the project. I realized it wasn’t just about the future of work, but about how everything that was changing was impacting our daily lives.
For example, remote work visas are allowing people with remote jobs to live in other countries. Borders may not be evaporating, but work borders, especially for tech talent, are changing. You don’t have to buy a house in one place anymore, and that shifts your entire lifestyle. This connects to bigger ideas about housing, like how long-term leases could be reevaluated and lead to empty buildings being repurposed for housing, potentially addressing the housing crisis. All these shifts impact not just how we work but how we want to live.
And so, I started realizing that all of these things tied together much more deeply. Which is why the project became *Future in Progress*. The book now explores these intersections of how we got here, what the future could look like, what’s happening now, and how past changes are affecting us today. It’s about understanding the real-world consequences of these shifts as they unfold.
DoneStreet
That's very cool. Have you ever heard of the book The Sovereign Individual?
Derrick
I have a book called The Working Sovereign by Axel Honneth on my bookshelf, but not The Sovereign Individual
DoneStreet
Ah, yes. I was going to suggest that The Sovereign Individual may be one that you want to add to the list because it discusses exactly what you’re speaking about here. The way the information age is going to really reshape how we live and organize and the idea of how the nation state may not be a thing anymore. Things like the breaking of borders. I think that you'd probably find it really interesting. It's a bit long, definitely offers some interesting insights though.
Derrick
I think that’s exactly it. A small example I was discussing recently is how things like coffee shops and restaurants have become more similar across the U.S. In the past, traveling from Atlanta to LA in the '90s meant experiencing distinct regional differences, different ways people talked, built, and even how restaurants looked. But now, with social media, everything goes viral. You see something in LA, like it, and then someone in San Francisco opens a similar shop. Even accents are changing because people hear more than just regional dialects that they’re exposed to voices on social media, YouTube, etc.
When I ask engineers in South America about my accent, they say I sound like the typical TV accent, which is wild. People are picking up these "social media accents" that cross regional boundaries. It’s happening with languages too, Italian, French, even English accents are starting to shift because of this global influence. And that’s an effect most people don’t think about. But it’s worth considering how this ease of crossing cultural and language barriers might change how we work in the future, especially as people can travel and live anywhere.
I could go on about this, but it all comes back to passion and curiosity. If you’re driven by those, it really opens up a lot of possibilities and you research and learn more.
DoneStreet
Yeah, this comes back to a lot of the conversations we have that usually get pretty deep and philosophical about the ways civilization is evolving. I hadn't really thought about the accent thing, but that makes total sense that. Everyone just has so much access to all the information in the world that it would blend together.
Derrick
It’s funny, because my family is mostly second or third generation from Mexico, but when my generation came around, they didn’t want us to learn Spanish. So from the late '80s to the '90s, anyone born in that time wasn’t taught Spanish. But then, as the world became more global, they decided to teach it again. So now my Spanish accent is very Americanized, but my French and Italian accents actually sound a bit more Spanish. It blows people’s minds when they hear it, and I honestly don’t know how to explain it.
You can see this shift over time. How you pick up accents based on what you hear. I remember when I first went to Spain, my Spanish accent was more like Catalan than actual Spanish, which was really interesting.
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