How Dovetail CEO Benjamin Humphrey scaled an Australian startup to global success

The average nonstop flight between Sydney and San Francisco takes around 15 hours.

For most of us, that could be the start of a memorable vacation, but for employees of customer insights hub Dovetail, it’s just part of the gig.*

Founded in 2017 by former Atlassian co-workers Benjamin Humphrey and Bradley Ayers, Dovetail analyzes sales calls, customer surveys, product research, usability testing and other forms of customer data so it can generate practical recommendations.

“We'll transcribe, summarize, highlight key moments, we'll break down documents for you. We'll extract insights and we make it all searchable as well,” said Benjamin, now the CEO, when I interviewed him in Dovetail’s SF office in June 2024.

“Our product is this customer insights hub, that's kind of the thing we're trying to create. We're in that group of startups — the category creators — which makes life, you know, fun, but also a bit challenging.”

Because Dovetail started up in Sydney, we spent a fair amount of time talking about building far from Silicon Valley: “Being kind of at the arse end of the world means that you're forced into being this kind of no-touch PLG business, because you can't easily go and have lots of conversations with people.”

Benjamin revisited the challenges he faced while trying to hire staff for a bootstrapped startup, as well as the impact of local networking and his early customer acquisition strategies.

“I always focused on North America and Europe at the outset because I figured they're the biggest markets by far for software, and that's where we're going to end up long term,” he said. “So why not start there at the beginning?”

This episode is the longest one in season 2 so far: we also discussed managing distributed teams, his personal development as a manager, and why he reconsidered his stance against taking VC funding. 

I also made sure to ask about ‘tall poppy syndrome,’ the peculiarly Australian cultural phenomenon where individuals who achieve success are sometimes criticized or cut down for standing out. Benjamin talked about how this mindset can impact entrepreneurs and leadership styles in Australia, and how he’s navigated it while building his company.

“I think you just have to develop a thick skin as a founder, and I enjoy coming to San Francisco because no one cares about that stuff in the Bay Area,” he said. “They're all just interested in the next hype cycle, the next big thing.”

*Dovetail employees get to keep their frequent-flier miles.

(03:26) How Dovetail’s customer insights hub works.

(05:14) “I’d always wanted to start a company.”

(9:19) “I got permission to basically start hacking on this little startup idea that I had in my spare time.”

(13:55) “We tossed around the idea of co-CEO for a while.”

(14:24) “Being kind of at the arse end of the world means that you're forced into being this no-touch PLG business." 

(23:24) “The design team is the best-placed team to figure out what the holistic solution is that's gonna solve for the requirements of individual customers.”

(26:50) How he promotes a cohesive culture across widely distributed teams.

(30:01) Relocating teams between Sydney and SF, annual retreats.

(33:47) “We only started doing paid ads about six months ago.”

(36:28) “I'm actually our Australian sales rep at the moment.”

(39:10) How hiring challenges led Benjamin to revisit his stance against VC funding.

(43:40) Tall poppy syndrome is real in Australia, but “you just have to develop a thick skin as a founder.”

(48:29) “And then you realize if you start hiring people, you have to do management.”

(52:39) His future plans for Dovetail.

(56:30) How AI integrates into his vision for the company.

(1:00:26) What he’s looking for as an angel investor, final thoughts.

Thanks for listening!

– Walter.