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

Fund/Build/Scale

In this episode, Fund/Build/Scale host Walter Thompson interviews Benjamin Humphrey, CEO and co-founder of Dovetail, a customer insights hub based in Sydney, Australia.

They discuss the challenges of hiring for a bootstrapped company, early customer acquisition strategies, and the impact of local networking when starting up far from major tech hubs like Silicon Valley.

Benjamin shares his journey from being a lead designer at Atlassian to founding Dovetail, emphasizing the importance of building strong customer relationships and adapting products to solve real-world problems.

The episode also explores managing distributed teams, transitioning from bootstrapped to funded, and leveraging AI to enhance business operations. Lastly, Humphrey offers advice on maintaining focus and managing expectations in a startup environment, particularly for those starting up outside the traditional tech hotspots.

EPISODE BREAKDOWN

(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 with 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.

Runtime: 01:03:59

LINKS

• Benjamin Humphrey
• Dovetail
• Blackbird VC
• Atlassian
• Just Ask!: 7 simple steps to unlock the power of clients, generate referrals and double your business, Graham Eisner
• Why You Only Need to Test with 5 Users, Jakob Nielsen
• Putting a Bolder Face on Google, The New York Times

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Thanks for listening!

– Walter.