I left Leapfrog on April 25, 2025, after nearly eight years. I’d joined back in August 2017, back when the company was still relatively small and nimble. Since then, I saw it scale to 450+ people. I had the chance to grow with it, lead some great teams, and learn from a wide range of projects across industries and continents.
So no, this wasn’t a quick exit. I spent about six months thinking through it. It wasn’t just about switching jobs — it was about moving into a fundamentally different kind of work. It was about shifting from designing within a system, to helping build the system itself.
Now, one month into my new role — leading product at a remote company that works asynchronously and builds for long-term scale — I’ve been reflecting on what’s different. And why this shift was necessary for me.
Leapfrog is great at what it does
Let’s get this out of the way — Leapfrog is doing exactly what it was designed to do: offer digital product development services to clients. That’s the business model. That’s the pitch. And it works. It creates predictable revenue, healthy margins, and a solid growth engine.
But here’s the thing: that model creates a certain type of work. Work that is fast-paced, externally driven, and deeply rooted in client requirements. The leads that come in dictate the kind of projects that go out. And sometimes those projects aren’t exciting, or clear, or even necessary — but they pay. That’s not wrong. That’s just how the system is set up.
What I realized over time, though, is that I had changed. I wasn’t content with creating surface-level clickable mockups or prettying up screens that were fundamentally disconnected from strategy. Clients often came in with fixed scopes, tight timelines, and very little wiggle room — and the team had no choice but to rush toward an arbitrary deadline.
Developers would push back with “that’s a design enhancement and will take longer,” and honestly, they weren’t wrong. We were constantly trying to cram a year’s worth of ambition into five months. Design was always the ketchup — squeezed on at the end of the burger, never part of the recipe. And that’s not something a services company is built to offer. Not consistently, anyway.
So what am I doing differently now?
One month into working on a real product — one that I didn’t pitch, that isn’t tied to a statement of work, that doesn’t have a client watching every move — I’ve felt the difference in every part of my day.
Fewer layers, more clarity
There’s no waterfall of strategy — design — handoff — development. Design is part of the strategy conversation. It’s not something that gets “approved” and passed along. We ship, we learn, we iterate. It’s cleaner, messier, faster, and slower — all at the same time.
No meetings unless we need one.
This one is underrated. My new team is async by default. If something can be said in Basecamp, it doesn’t need to be a meeting. I used to lose my creative-juice time to “quick syncs” that solved nothing. Project managers at Leapfrog used to send Google Meet invite to something they could’ve just responded in Slack. Now I block my own calendar. I actually get to work.
Creative work isn’t linear
One thing I wish more people understood — especially in service environments — is that creative work isn’t binary. It’s not a faucet you turn on and expect consistent flow. Some weeks a designer can produce $1 million worth of insight, clarity, and direction in a single breakthrough. And some weeks, they’ll need to stare at the ceiling, go for long walks, or binge Netflix before they arrive at something that actually moves the needle.
But service company timelines rarely allow for that kind of ebb and flow. Discovery and design are expected to fit into four-week or six-week boxes, pre-scoped and pre-approved, regardless of what the problem actually needs. The clock keeps ticking — even when the idea isn’t ready yet.
“Remote-First” or “Not Remote-First” is a fundamental contradiction
It’s especially frustrating when the operational setup doesn’t even support the thing it’s trying to enforce. You’re asked to work from office— often just to look available — while your stakeholders and clients are remote, in wildly different time zones. The structure feels rigid, while the work demands flexibility. There’s a fundamental mismatch there. Creativity needs space, not physical presence. It needs trust, not time-tracking.
This mismatch doesn’t just affect output — it affects morale. It subtly tells people that presence matters more than progress, and that’s when the most talented folks start tuning out.
Responsibility is real
When you’re building a product, there’s no one to blame but yourself. There’s no client to scapegoat, no project manager to smooth over a delay. You’re accountable to the user, the market, and the team. That can be intense, but also incredibly energizing.
Design is not decoration
It’s not “make it look better” anymore. It’s “what should this be?” That level of ownership rewires your thinking. You’re not crafting experiences from briefs. You’re co-creating the product from first principles.
Product is not the easy path
I want to be clear about something: switching from services to product isn’t some clean upgrade. It’s not more glamorous or easier. If anything, it’s harder in ways I didn’t fully expect. There’s more ambiguity, more ownership, and fewer buffers. There’s no client to absorb the fallout when things don’t land. No project manager smoothing over complexity. It’s just you, your team, and the question: does this actually work?
The metrics aren’t as immediate. The validation takes longer. The pace feels slower, but the pressure runs deeper. You’re not handing over deliverables — you’re living with decisions.
And that weight is real. But it’s also what I was looking for.
You grow differently in a product organization
At Leapfrog, I learned how to work fast, collaborate well, and polish things to a shine. That kind of craft is invaluable. But eventually, I found myself wanting a different kind of growth — not vertical, but foundational.
In product, growth isn’t about mastering the tools or moving up the ladder. It’s about sitting with uncertainty. Owning outcomes. Thinking in terms of systems, not just screens. There’s no applause for a clever design unless it moves the needle. There’s no “done” unless it holds up in the wild.
That kind of growth is slower. Less visible. But it rewires how you think, not just how you work.
What I’ve realized — one month into this new role — is that I’m not chasing excitement or variety anymore. I’m chasing clarity. Purpose. Work that feels connected end-to-end, even if that means fewer projects and longer feedback loops.
I’m okay being in a room with no clear answers — as long as I’m in the room where those answers are being shaped. I don’t want to decorate ideas anymore. I want to help build them from scratch.
I’m not anti-service agency, or anti-client work. I spent years doing that work with people I respect, and I still believe it can be a great way to build skill and stamina. But for me — at this point in my career — it stopped being enough.
Now, I’m building something with a small, scrappy team, in silence, without much fanfare. We talk less, write more, and ship often. It’s still early days — and while I’m not sharing specifics about the company or role just yet (we launch in November 2025), that’s by design. I’m letting the work speak first.
And somehow, that quiet rhythm has brought me back to what I actually care about: making things that matter, and making them well. I don’t know if this is the final form of my work life. Probably not. But it’s the most aligned I’ve felt in a long time.
And that’s a pretty good place to start from.