Stripe CTO on maintaining small teams in big business

15 Jun 2023

David Singleton, Stripe. Image: Elaine Burke

In the latest episode of For Tech’s Sake, we sat down with David Singleton, chief technology officer at Stripe, to examine what disruption really means in the world of tech and how Stripe scales up.

When we think about the big disruptors of tech, we might think of what some of the now tech behemoths once did.

Microsoft put computers into our homes, Apple revolutionised the idea of the smartphone, Facebook – now Meta – could be considered the original face for social media and Amazon completely disrupted the e-commerce industry.

But the thing about disruption is, it keeps happening no matter what the norm is and no matter who is at the top of the pile driving said norm.

With several of those disruptive tech companies becoming million, billion and even trillion-dollar companies and their once revolutionary technologies becoming standard practice, it’s time for the new kids in town to disrupt the way we live and work.

So, what does tech disruption look like in the new world of web? To help understand the current landscape, For Tech’s Sake hosts Jenny Darmody and Elaine Burke sat down with David Singleton, the CTO of multibillion-dollar Irish-founded fintech Stripe.

Singleton has been a fintech whizz ever since he built some invoicing software for his parents when he was a kid. But before he was the technical lead of Stripe, he spent many years in engineering at Google.

Google was once among the born-on-the-internet companies disrupting industry incumbents, but now it’s one the Big Tech behemoths eating up small businesses that threaten their dominance.

Having been at Stripe for five years, Singleton said one of the things he loves about working there is helping companies take off that “wouldn’t otherwise get started”.

“We do that by providing infrastructure. That means that the small companies in the world, the founders can actually get access to the world’s financial system, in the same way that incumbents have large enterprises.”

Bringing small teams to big companies

As part of a fintech that has become a multibillion-dollar giant embedded in the world’s financial infrastructure, you’d be forgiven for assuming Stripe now operates just like any other large company.

But Singleton also spoke about the importance of maintaining certain elements of start-up culture while rapidly scaling up to become tech giants.

“Small teams work much more effectively together than large teams, mostly because of how many lines of communication you have to have between people,” he said.

“It actually grows with the square of the number of people so as you add one person to your team, you don’t just add one incremental unit of it being more difficult to collaborate together, you add many more lines of communication.”

However, as companies who want and need to scale, he said it’s vital to get the units of the small teams right so that each team has one thing to work on that they understand really well that can be built on.

“That creates an organisation that can get a tonne more done than an organisation where everyone has to collaborate with everyone else in order to move forward.”

Check out the full episode with Singleton wherever you get your podcasts and subscribe for more.

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