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Eight years inside government, eight years helping build Agile Six. Through it all, Dan Levenson has never stopped asking one question: Who did we help?
Not the number of contracts signed or the billions spent, but whether any of it actually helped someone. Now, as President and CEO, he's leading Agile Six through graduation, guiding the company toward becoming 100% employee-owned, and proving that a different way of working isn't just possible. It's already working.
In this conversation, Dan reflects on the choices that have shaped Agile Six and what it takes to build a company where people come first, not just in principle, but in practice.
Meet Dan Levenson
Dan, welcome. To kick things off, tell us a little bit about yourself. Who is Dan Levenson?
Dan: I'm a father of two young boys. I'm also a partner to my wonderful wife, Anna. I'm a son, a brother, and a friend. My life really revolves around my family.
When I'm not working, I spend most of my time hiking with my boys and our dog, reading books, playing games, and being with my family. That is really what fills my cup and makes me whole. One of my hobbies is yard work. I actually really enjoy mowing my lawn. There's a sense of peace and tranquility that comes with that.
I'm fiercely loyal to Maryland and Baltimore, where I come from. I went to the University of Maryland, as did my brother and sister, and my parents and grandparents. My family has a long history in Baltimore, being sports fans back to the Colts, Ravens, and Orioles. It's something really important to my grandparents, my parents, me, and my boys as well. It's a sense of who we are, not just a hobby or activity.
My wife and I really enjoy traveling. I'm excited to experience new cultures through my boys and to see them enjoy these things for the first time.
Tell me about some of the personal experiences that helped shape who you are today.
Dan: Being in service of something has always been important to me. I think it starts with my grandparents. Both of my grandfathers served in the military in World War II. Hearing stories from them and understanding that level of sacrifice set the foundation that I've always wanted my life to be in service of something important, something meaningful.
I also learned a lot about service from my parents. Both were home-health physical therapists who traveled to people's houses, generally serving people who were homebound and needed physical therapy support. My father was one of those people who would wake up, pack his lunch, and never miss a day of work. That didn't just apply to his job, but also to coaching sports teams, picking kids up from school, or taking them to different activities. My dad set a real example for how I show up for my kids and my family today.
My mom took a different approach. The term human-centered wasn't necessarily used back then, but that's how I always saw what my mom did. At times, she would spend two or three extra hours with patients because she saw them as human beings.
I think I was in high school when my mom had a patient she got to know over time. This patient was not able to walk. While the hospital and doctors said, “You're bedbound,” my mom decided to help her by creating a kind of shift board. She got my friend and me to help with a little woodworking and create this board so the woman could independently use the bathroom. That may not sound like a big deal, but watching my mom put other people first, take the time to see people as real human beings, and care about the little things that matter so much in someone's life really shaped how I approach my work and life today.
When I joined federal service, something clicked. I knew this was the way I could give back.
The $8 Billion Question: Who Did We Help?
You've seen the system from both sides. So take me back to the moment that you started asking yourself, “Who's this actually helping?”
Dan: I joined the Centers for Medicare and Medicaid Services after the Affordable Care Act was passed. I started in 2010. I really didn't know much about the inner workings of government. I just assumed: this is Medicare, this is Medicaid, people have it figured out. I started as a GS-7 in the 1102 business contracting field.
The big moment that really stands out for me came a few months after I started. It was the end of the fiscal year, and we were meeting as a group of 1102s — about 150 or so of us. I remember there was a presentation, and the slide roughly said that our office had completed over 2,000 contract actions and committed over $8 billion.
That was an applause line, and everybody just started cheering. I broke out in a cold sweat, thinking: that's not inherently good or bad. Who did we help? Did we provide value for that $8 billion? Did we actually respond to people's needs? From that moment on, I can't ever unsee the things that I saw.
As I think about it now, it's confusing outputs for outcomes. There was a lot of output that my office had, but what I really cared about was it being in service of positive outcomes for the people we were trying to help. Those are the questions I started asking, and I don't think I've let up even to this day.
Finding a Better Way
Let's talk about how you believed there had to be a better way.
Dan: At our core, we have that belief that we can be successful doing things a different way. Ultimately, I go back to the partnership that I formed with Robert Rasmussen, the outgoing CEO and chairman of the board. Robert's greatest passion, from his years spent abroad and with other government contractors, was trying to create a better place to work. My time in government was really focused on showing that we can have more positive outcomes — the better work to do.
As Robert and I got to know each other, we learned that the things we were most passionate about — better work to do and a better place to work — really couldn't exist without each other. It helped set the foundation for what Agile Six has become.
Graduation to 100% Employee Ownership
You're stepping into the CEO role at a time of real change. Agile Six is graduating. So what does this moment mean, and what changes?
Dan: Graduation is a really big moment for a company, and to be honest, this is not the moment that I would have picked. The last year or two have been really disruptive, and I never quite drew it up as graduating in a year when we were already having to reshuffle. But that's reality, and real opportunity has come with this: the chance to build this company for 2026 and beyond, on a foundation that understands this modern ecosystem from both a technology and people perspective. When things are going great, it's a lot harder to look down and say, “Hey, are there some foundational things that maybe we should look at?” It's almost like technical debt, but for a company.
I truly believe that's going to be a differentiator as we get back into growing and continuing to scale, but this time on a steadier and stronger foundation that meets the moment of the times we're in.
With that, I have to speak, of course, about our employee stock ownership plan, because graduating allows my partner and friend Robert to no longer be the majority stakeholder in Agile Six. That's opened the door for us to actually move forward and execute on becoming 100% employee-owned. It's something we've been talking about for a long time, so I think that's incredibly meaningful in its own right.
I'd like to spend a little more time on the ESOP, because it's such a big part of Agile Six's future. There were a lot of different paths you could have taken. Why this way?
Dan: The ESOP going to 100% employee-owned is the thing I'm most passionate and most excited about. But I also think it matters as much for what it is as for what it's not. What it's not is bringing in an outside investor or private equity with strings attached. I trust and care about everyone at Agile Six way too much to do that and then tell them nothing will change.
So for us, it's the right thing to do morally, but it's also a powerful business incentive. Looking back, I know how motivating it was for me to come in as an owner at Agile Six when I joined. It's just a different level of skin in the game, and being able to offer that to everyone at Agile Six is going to be such a powerful differentiator, especially as people get closer and closer to the value creation, with AI and other modern tools.
The ESOP is incredibly important: making sure that everyone has that connection to the value we're creating and to the work we're doing as a company. That's great in years when we're thriving and profitable as a business. But even in our hardest year, this past year, we were still able to make a meaningful ESOP contribution. It wasn't as big as it is during other years, but when times are the hardest, that's when it matters most. We're all putting that effort in. We should all share in the wealth and the value being created.
People First in the Age of AI
Now let's talk about Agile Six and AI.
Dan: We built Agile Six as a people-first company at a time when that was mostly a philosophy, especially within government contracting. It was against the grain. We believed in trusting people, putting decisions where the information actually is, and giving small teams of good people the space to do good work. Something really exciting to me about the time we're in right now is that I feel like technology has finally caught up to that bet.
AI is increasingly good enough to take on some of that repetitive work, but that work was never the reason anyone came to Agile Six in the first place. As AI can take on more of that work, I think the things we built this company around are becoming more valuable, not less. When execution gets cheaper and information gets easier to access, that scarce resource becomes human judgment. It becomes trust, purpose, prioritization, knowing what really matters right now. How can we make a good decision closest to the work? If we're supporting Veterans, the important question isn't, can we produce more stuff or more activities? It's whether we can understand what's most important for the Veteran right now, and let's work on that.
The cost, the speed, and the capacity of knowledge work are changing this quickly. What does that mean about how we design organizations? What does that mean about team size, incentives, planning, how the government buys? Those are the questions that I keep coming back to. I truly believe that the more capable technology gets around us, the less excuse we have to continue to have bad systems around good people.
I look at a lot of traditional companies — honestly, most companies in the space — and they try to retrofit humanity onto what they've built as an efficiency machine in response to government. At Agile Six, we've tried to come at it from the other direction: building a company around humans. I think now we have the ability to dramatically add more efficiency on top of that.
It's really important to stay pragmatic about this. AI isn't magic, it's not a silver bullet, and it does not replace all the hard parts of the work. On our Benefits Intake Optimization work at the VA (BIO), for example, we probably leveraged AI for about 15% of the work. It gave us real leverage, saved weeks of setup, and was really helpful, but the people did the rest of it. The judgment, relationships, trust, and adaptation that led to delivery — those were all human. Ultimately, the question isn't really, is AI going to change how we deliver? Of course it will. The question is, who's going to benefit when productivity goes up? At Agile Six, our answer is the people who create it.
Same Mission, New Markets
And what about who Agile Six supports? Are there any changes happening there?
Dan: I want to start by being really clear about something. The federal government is the core of Agile Six, and it will always stay the core as long as I'm here. The VA, CMS, HHS — those are the missions that we exist to support. We were literally founded on those missions, and that's why I'm here. None of that changes because we're exploring commercial work. But we are diversifying, and there are a few reasons for that.
There are parts of the commercial market that are already moving incredibly quickly toward AI and automation. There are new AI-native companies being built with that automation in their bones rather than bolting it on afterward. If Agile Six said we're going to come to those markets as a traditional digital services company saying, “Hey, look at this great work we did at VA,” I don't think that would be especially differentiating. In most cases, I don't think it would be very cost-competitive either. But we think there's a much more interesting opening in regulated industries. Healthcare is an obvious example, because those organizations have to answer the hard questions, just like in the government. What should you automate when the stakes are really high? What should remain human? What happens when the rules exist for a good reason, and if you get it wrong, it actually affects somebody's life?
That's where I think there's something for us to learn and something useful for us to contribute. This is the hypothesis that we're testing in Agile Six: let's go where those hard questions are already emerging. Build that foundation and infrastructure for scaling AI responsibly. We want to learn that middle ground firsthand. As with everything, we're going to sense and respond. There's not a rigid five-year plan where we already have all the answers.
To me, being a trusted advisor means doing the learning before your partner actually needs the answer. When a government customer inevitably asks us: What can safely be automated here? What still needs human judgment? What risks are real? What are the controls that actually work here? I don't want us answering from a theoretical place or from a slide deck.
My partner Robert has described this as us being plumbers, and I think that's right. Somebody has to figure out what the pipes for this modern world look like. How do AI agents and systems safely connect? Where does authority live? How do you control access? How do you know what happened? This isn't the glamorous part of AI, but we think it's going to be incredibly important.
I also see the irony that we're leaning into technology that's disrupting our own industry. But I would rather understand it deeply, help shape it responsibly, and be part of the solution than spend all our time trying to protect a model that is inevitably changing around us.
There are also business reasons for diversification. Different markets make Agile Six more durable and resilient. A more resilient Agile Six can better keep our promises to the people it serves, across different markets, seasons, administrations, and within Agile Six. Keeping those promises matters as much to me as anything else.
The Honest Broker
Part of building that trusted partnership is being willing to call things out, even when they're uncomfortable. So what does it take to be that honest, trusted partner in government?
Dan: To call out the system — or things that may actually be leading to bad outcomes or challenges in delivery — you have to be willing to have those honest conversations that help us all get better. That's the importance of meeting people where they are, building relationships, building trust. Then, when we do find challenges or things we think could be better, collectively, how can we look at this, take an honest accounting of where we are and the outcomes it's leading to, and try to show that there's a better way? It means being humble enough to know that we don't have all the answers. But what we do know is that when something hasn't been working, we can't just keep doing the same thing and expect different outcomes or different results. I use the words honest broker a lot, and that's really what we strive to be.
To build that trust — to be the company that government may not always want but really needs, to be that best partner — this goes back to empowering people. It's the people on the ground doing the work who see, every day, the things that are working and the things that aren't, and who often have the ideas for how we can affect positive change and make a difference. Those people being trusted to act on that, to communicate, and to pull in others as makes sense — so we can collectively have the relationship, the trust, and the knowledge to not only say, “Hey, this thing isn't working,” but come to the table with real ideas.
How Agile Six Works
You said something to me once that I've never forgotten. It was the way you described how everything works together at Agile Six. Take us through that.
Dan: We always strive to have this coherency across our business. At Agile Six, I've come to describing the company really similar to the human body. Everything is related, and we always strive for that harmony within. I like to think of our operations — the basics of the company — as the bones. That's the skeleton that everything exists on. The people operations and our folks — that's the heart, the circulatory system, the lifeblood of Agile Six. Our delivery is our muscle. That's where we're actually taking things to ground, taking value to the market. The brain and the nervous system is strategy — and it doesn't just start with me, of course. Strategy may at times emanate from me or my vision as CEO, but more importantly, strategy is understood and gets to every part of the body.
I feel like this human body analogy really is more honest and authentic. A company is a real and living thing, and there are different seasons the company may go through, just like different seasons in life.
We talked a lot about doing things differently. So if someone were to ask you what makes Agile Six different, what would you tell them?
Dan: People always ask, “What does make you different?” We may answer: it's our culture and our values, our employee stock ownership. But I don't think any of those on its own is what really defines us as a company. It's all of these things and that unique combination that makes Agile Six different — from our focus on outcomes, to empowering decision-making where the information is, to really living our values, to the employee stock ownership plan as our exit strategy.
I think it's increasingly important that we really name it and take ownership of this. I've started referring to that as the a6 OS. That allows people who've been here building with me for a decade or even longer in some cases — we should take pride in what we've built together, and also be able to ground everything we've built in something tangible, something we can name.
As Agile Six continues to evolve, we're going to keep learning from and borrowing the best bits from self-management, agile, human-centered design, and whatever helps us. But Agile Six is truly the sun at the center of the orbit, not the other way around.
Governed Autonomy
So how do you design a company to work that way?
Dan: I've always believed that systems outperform intentions. You can have really good people who want to do the right thing, but if the system around them keeps pushing them toward the wrong behavior, the system almost always wins out. Good people under pressure need good systems, not heroics. It should be easy to do the right thing. I think that belief has probably its biggest test and also its biggest opportunity right now.
At Agile Six, as I mentioned, we're not just trying to bolt AI onto the company we already have. We're asking how the company itself should change alongside the technology. What do teams look like? What should leaders actually own? What decisions sit close to the work? What should technology carry that used to require layers of coordination? It's important as a company that we're the first place testing those hypotheses. I think our advantage can come from being willing to redesign the model itself instead of inserting a new tool into an old model.
That's the tension that Robert and I have wrestled with for years. How do you give teams real freedom without leadership eventually pulling everything back into command and control? On the other side, how do you avoid autonomy becoming the Wild West, where nobody can actually understand what's happening or what's producing value? We've come to call this middle ground governed autonomy. Leadership knows the outcomes, the boundaries, and the evidence, but teams keep the how.
That brings up a really important point: when we have better evidence and validated learning, that should buy more autonomy, not more surveillance. For years, governments and other institutions have compensated for weak information by adding more layers of oversight — more reports, more process, more PMOs, more people checking on other people. In my experience, that usually creates a false sense of security. If you can actually verify what's happening and what was delivered, we should be able to give capable teams of people more room to move and more autonomy, not less. In some cases, this evidence is actually the permission structure that's going to let a risk-averse leader say yes to something different, to something new. The reporting machinery, the documentation — that's not the point. The point is making trust durable. Having trust, but with receipts.
The Next Chapter
Sixteen years ago, you asked yourself, “Who did we help?” Are you still asking that question today?
Dan: That question I've never let go of: Who did we help? This year, something happened that I wasn't sure I would see in this ecosystem. A government customer asked us to help design work around verified delivery and outcomes. We've helped design it. We proposed it, and it's still moving through the process, and I don't want to overstate where we are. But even being asked the question is meaningful to me. For years, I've wanted companies to be able to compete on the actual value they deliver, and now we're getting a chance to really help figure out what that looks like.
Where does Agile Six go from here?
Dan: Government has gotten very good at accounting for hours. But I truly believe that the next decade is going to belong to companies that can account for value. Not all spending is created equal. Some spending is part of the solution, some of it sustains the problem, and government needs a way to tell the difference. That's the problem I've been chasing since that room at CMS 16 years ago.
It's also why this next chapter at Agile Six makes so much sense to me. We started a decade ago helping organizations think about agility at scale. The question in front of us now is: what does agility at scale look like in an AI environment? I see an Agile Six that is fully employee-owned, AI-native, trusted across federal and beyond, but still built around small and fast teams and still working really close to the people we're supposed to be helping.
After 16 years of pulling at this same thread, I feel like the technology, the market, what customers are asking for, and what we're becoming ourselves at Agile Six are all starting to converge. It's hard right now — I'm not going to pretend otherwise — but the opportunity to actually make a difference feels bigger than it ever has in my career. And I can't think of anything else I'd rather be working on, or people I'd rather be doing it with.
Dan, thanks for sharing your story and Agile Six's next chapter.
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