Bryan Irace on finding the middle in NYC

Feb 6 · 4 min read
Bryan is an engineering manager on Stripe Capital.

A Hemingway for our time might say that “a startup fails two ways: gradually, then suddenly.” Gradually, my company spent three hard years failing to find product-market fit. Suddenly, last January, I found myself unemployed for the first time.

To make matters worse, I didn’t have a next step in mind. When working at an investment bank, I wanted to move into tech. Once in tech, I was drawn to try building something new. That new company didn’t work. Now what?

Lacking concrete direction, I fell back on guiding principles. I enjoyed the early stage but it had left me emotionally drained. I was open to joining somewhere more established but didn’t want to lose what I had really come to cherish: working as a generalist towards a vast, untapped opportunity.

New companies are increasingly choosing to break ground in NYC, and technology’s biggest incumbents continue to grow their presences here. I’ve been to both extremes, having previously joined companies with 30,000, sixty, and four employees. Something in the middle, however? It wasn’t clear that I’d find it here.

I’ve been working in NYC since 2008. Around that time, it seemed inevitable that a select few tech companies would continue their ascensions, their early employees peeling off to fertilize the next wave. This didn’t quite happen, or at least not to the extent that I had hoped. Almost all who met my criteria this time—later-stage but still on an exciting trajectory—were based elsewhere. Of those, I struggled to find one with an NYC office whose mandate matched what I was looking for. Despite this, Brooklyn is our home and I didn’t consider roles elsewhere.

I sought this trajectory in part because opportunities have higher liquidity during times of growth—as companies expand, today’s projects become tomorrow’s teams in need of leadership. I’ve switched roles a few times in my career and strongly believe in the value of the engineering/manager pendulum. I had just spent three years doing both at the same time, which wouldn’t be justifiable on a larger team. As such, I looked for a company that would support such transitions with deftness and encouragement, while having the growth to accommodate them.

In Stripe NYC, I found a growing team with authentic distributed work DNA, building new products atop a world-class foundation. Products expected to help define the future of the company and Internet businesses more broadly. I’m incredibly lucky to have joined this past April.

Coming from a ten person startup, it’s easy to naively view 2,000- and 100,000-person companies as comparable despite their not being remotely similar in practice. Stripe has grown but continues to feel small due to how tightly the company focuses on user-centric financial infrastructure. Find yourself across the lunch table from someone who you’ve never met and the odds are incredibly high that there’s alignment between what you each work on. Even new “bets” like Capital and Corporate Card have strong synergies with our core businesses, providing a unique respite from startup life that retains many of its desirable traits.

More than two-thirds of respondents to a 2019 survey cite tools such as Stripe as the primary enabler of international expansion, well above funding, physical infrastructure, or government support. Just as the Stripe product aims to free businesses from geographical shackles, the Stripe company treats itself in similar regard. Why exactly does Stripe have an office in NYC? With fourteen offices and hundreds of remote employees, there’s less bespoke justification required. Stripe is here because ideally, we’d be in as many places as possible. Years of thoughtful dispersion in service of this mission have boosted productivity as opposed to stifling it.

As for me, I joined as an engineer yet moved into management eight months later. This wasn’t the plan, but my faith in Stripe’s ability to help me navigate these kinds of career inflection points proved warranted. Management at Stripe is not a promotion, which keeps incentives aligned during the growth spurts that new teams and the NYC office more broadly are going through. I couldn’t be more thankful for the support that I’ve received from my colleagues, especially as I’m about to be leaving them for four months.

Early-stage product development doesn’t require high risks and high rewards. While “startups within big companies” don’t exist, that doesn’t mean there isn’t a middle to be found.

When I return, Stripe will be even larger but the characteristics that make it feel small will persist.

Interested in learning more about opportunities at Stripe?


Life at Stripe

Stripes around the globe are working together to increase…


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Life at Stripe

Stripes around the globe are working together to increase the GDP of the internet.

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