A Rollercoaster Year
It's surreal to look back and realize it's been a year since I joined Typeface, and even more surreal to realize that the chapter is already closing.
Few people get the chance to join a startup in its earliest stages. You step into something that's still being shaped, and it ends up shaping you more than you might ever expect. Joining Typeface straight out of college, I came in with zero expectations — just pure nerves and excitement. It was overwhelming at first, but in a good way.
And somewhere along the line, it stopped being just a job, and took a bigger part in my life.
1. Joining at Full Speed
When I joined Typeface, the Ads team was still in its earliest stages. There was no real product, no playbook, and definitely no rules. It felt like everyone was starting from a clean slate, and the opportunities were endless. The future was bright.
My first month happened to coincide with the year-end holiday party. Just as soon as I had finished my starter tickets, we were already joining the Seattle, New York, and India teams to celebrate the new year. It was at that moment that I remember feeling like I had stumbled upon something special — that this small team of scrappy, bright-eyed individuals had the potential to compete with giants like Adobe, OpenAI, and Anthropic.
I didn't fully understand it then, but I had just entered one of the most intense learning periods of my career.
2. The Rollercoaster
There's no better word for this past year.
The Highs
I got to witness the birth and evolution of Ads Arc. What started off as a clunky HTML prototype quickly became a canvas-driven, Figma-like editor used by top enterprise customers.
I watched Ads become the highest revenue generator in the company.
I saw the team grow, the product stabilize, and the business mature.
There were weeks where the energy was electric, when you could see every person in the room buying into the same vision.
One of my favorite memories from the year was being invited to Seattle for a week during the height of our Spaces migration.
There was something about being in that small, somewhat cramped office overlooking East Lake Union that made it feel personal. For the first time, I was working shoulder-to-shoulder with the entire team: meeting people I had only seen on Zoom, but had gone to war with.
There was one night in particualr where the team went out for bowling after a long day. While I placed dead last each round, I look back on that night as a rare moment of us taking a step back. We swapped stories about the chaos the past few months had been, and took some time to appreciate how far we've come.
These moments felt like hitting the peak of the rollercoaster.
They're the memories that make the chaos worth it, the ones that remind you why you joined in the first place.
The Lows
For all the highs, there were stretches of this year that were incredibly hard.
Startup life has a way of compressing time. Days blur into weeks blur into months, and looking back just one quarter feels like digging deep into the past.
I still have a visceral reaction to the phrase "SVG color picker." I remember working until three in the morning to implement that feature for a customer demo. It was a relic from our old HTML editor, long forgotten after we migrated to manifest-based ads. No one remembered it until an urgent ask from a multi-million-dollar enterprise customer exposed the gap.
I remember pushing the last PR half-delirious, praying it would be merged without any issues by the time I woke up in a few hours. But it was that level of urgency that became the baseline.
Then there was the weekend before the Microsoft demo. Scaling ads had never been given real attention. It started as a POC one engineer had built months earlier, something most of us in Ads barely had any context on. And then, almost overnight, it became the only thing that mattered. Both the Ads and ML teams were pulled in to work that entire weekend, scrambling to put out fires, and duct-tape the system into something presentable.
It was these moments that created a strange sense of shared trauma within the team. And it wasn't just the late nights. It was the constant feeling that there was always one more issue to fix, one more blocker to handle, one more demo to prep for. You'd close one ticket, only to find three new ones waiting. After a while, the cycle starts to feel endless.
That's the thing about burnout. It doesn't always make a loud appearance. It speaks quietly, in faint whispers. First through small things: not taking the time to celebrate wins, or rushing straight to the next task. Eventually you start measuring yourself by your output alone, and the only question you can hear in your head is, "What's next?" Not out of ambition, but out of fear of falling behind.
And beneath all of it was the same tension many fast-growing startups share: a team that deeply cares, but is always stretched just a bit too thin. Everyone wants the product to succeed. Everyone pushes themselves for the sake of the company, the team, and our future. But caring that much for that long can become its own kind of weight.
These weren't the moments I'll look back on fondly. Nevertheless, they were part of my journey: one that has been as emotional as it is professional. They've taught me what my limits actually are, and what it feels like to ignore them for too long. They reminded me that ambition without boundaries can become something destructive, even when the right intentions are there.
There were times when the pressure had felt insurmountable. And yet, even in the hardest moments, I had never felt alone. The shared struggles and wins alike built bonds that only people who have been through it can understand. It wasn't healthy, and it wasn't sustainable, but it was real.
3. Navigating Ambiguity
If there's one lesson that kept resurfacing this year, it's that startups amplify whatever you lean into. Whether that's curiosity, ownership, or sheer stubbornness, the things you choose to touch have a funny way of becoming yours.
In bigger companies, you're handed well-defined problems. At a startup, you're handed something closer to a blank page. I walked into more than a few projects where the only real clarity was "this is important" and everything else was up to me to figure out.
The social post variations refactor is a good example. I brought up the problem as a casual pain point, half expecting it to be pushed down the backlog. Instead, my tech lead told me to write a doc, explore approaches, and take it on as a project. Suddenly, I was coordinating architectural decisions and owning something I hadn't even planned on working on two days earlier.
That's the thing about ambiguity at startups: if you notice a problem and say it out loud, it often becomes yours.
4. Ownership by Accident
Some ownership you choose. Others choose you.
During our migration from HTML to manifest-based ads, I was tasked with integrating the image copilot into our new editor. Little did I know, this one piece of legacy code ended up sticking around through multiple editor revisions, even as we moved all the way to Spaces. And what I thought would be a one-off task ended up blooming into a personal responsibility for me to uphold when it came to any and all copilot-related issues.
Whenever there was a bug with image generation, asset upload, or even an incident affecting a customer, I became the person people went to.
Not because I was the most qualified, but because I had context. And context is currency at a startup.
That's something I learned quickly: expertise forms around whoever cares enough to dive in first.
Responsibility Isn't Assigned - It Emerges
The longer I worked at Typeface, the more I realized that responsibility wasn't something handed down from above. If anything, it bubbled up from below. You raise your hand, and suddenly you're leading something. You identify a gap, and suddenly you're the owner of the solution.
It can be empowering and terrifying at the same time.
But it also taught me a lot about myself — that I do my best work when the path isn't fully paved, and when I'm forced to think beyond my ticket list and see the bigger picture.
Thinking Bigger
"Think bigger, Jonathan" was one of my tech lead's favorite phrases to me. And truth be told, this year forced me to zoom out in ways I wasn't used to. In all of my previous work, I was focused on delivering the task in front of me. At Typeface, I had to pay attention to why something mattered at all.
Learning to question why decisions were made just as often as making them reshaped the way I worked. It made my decisions faster, not slower. It helped me prioritize what actually mattered. And it made me realize that engineering, especially at a startup, is as much a strategic job as it is a technical one.
5. Looking Ahead
As I wrap up this chapter, I feel a bittersweet combination of gratitude and excitement.
I'm grateful for the incredible engineers, designers, and leaders I got to work with. In many ways, Typeface has shown me what a small group of amazing people can accomplish together, and what it means to truly have a great culture that's centered around people.
And I'm excited for what's next. Joining Amplitude as a Software Engineer II in the Product Adoption org, where the entire mission is to help users not just try a product, but to grow alongside it.
In many ways, it feels like a natural next step. After a year focused on understanding how users think, where products fall short, and how adoption happens (or doesn't), I'm stepping into a role built around exactly those questions.
If this year taught me anything, it's this:
You don't grow by waiting for certainty.
You grow by stepping into the unknown, again and again, until it becomes familiar.
So here's to the next chapter, and to everything that came before it.