How Dovetail's Benjamin Humphrey Makes the Office Awesome

Benjamin Humphrey

How does a Sydney startup maintain close to 100 per cent staff retention? Against all the trends, Dovetail CEO Benjamin Humphrey makes sure the office is awesome.

07:00 I check Slack before I even get out of bed. Ninety-three per cent of our customers are overseas and there’s activity overnight in our San Francisco office. [Companies including Atlassian and Shopify use Dovetail software to analyse customer and internal data.] I look at the Net Promoter Score and read individual responses. Then I clear or snooze emails, look at plans for a house I’m building for my mum and check my sleep score on my smart watch.

08:00 Walk to our office in Surry Hills, listening to the Wild Hearts podcast. Its host is a friend, Mason Yates, who’s interviewing another friend, Tim Doyle from [healthcare technology company] Eucalyptus. Tim and I are in a WhatsApp group for Sydney founders that meets for dinner each month. We’re always on chat. The six of us share frustrations and stories you can’t tell your team and all kinds of tactical stuff: “What do you pay for this kind of role?”

09:00 The whole company is in the lounge for the all-hands, with catering from [Sydney eatery] The Grounds of Alexandria. I tailor the founder update to address cultural things; we’re 70 staff in Sydney and people naturally diverge as a team grows. When I gave a talk on how we were becoming waterfall-y– handing things over – I came up with this ironic acronym, HCCF, which stands for Highly Collaborative Cross- Functional. It was a joke but suddenly there was a Slack emoji and now it’s on a mural.

09:45 Usually there’s a guest speaker but today our head of product interviews our new head of operations. Then we have a rapid-fire Q&A with new hires: Netflix or YouTube? Beach or mountains? If you could eat only one food for the rest of your life, what would it be? We end with a founder Q&A. People often ask Brad [Ayers, co-founder and CTO] and me about the next office because we’re always running out of space.

11:00 Every three weeks I have an executive coaching session with Ed Batista, who lives on a farm north of San Francisco but used to be a lecturer at the Stanford Graduate School of Business. Today we talk about having a consistent level of assertiveness that’s just enough that people understand critical feedback. The one-hour sessions are superexpensive – [venture capital firm] Felicis Ventures has a program where one per cent of an investment goes towards founder and CEO training – so I try to get the most out of them.

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12:00 It’s an eight-minute walk to City Edge, where a bunch of us grab sandwiches. On the way back up the hill, I read research on our pricing and packaging project. Some feedback says the new stuff can be confusing. We’ll change it.

12:30 Pretty much everybody has lunch at the same time at two farmhouse-style tables. We’ve consciously invested in positioning ourselves as an in-person company while companies like Atlassian and Canva go remote. The average age in our team is 28 and a lot of people live close to the office so it’s a very social vibe. I get a game of pool in. It’s not mandatory to come in. We have people dial into the All Hands but we’re not going to optimise the experience for remote. The way I put it is if you’re not working in the office, you’re going to have mad FOMO. There’s an espresso machine and two beer taps but we also do workshops, whiteboard sessions, brainstorms and lots of catered events, such as an LGBTQ+ panel discussion with live drag bingo afterwards.

13:00 A founder check-in with a product team to discuss Figma designs for a hashtagstyle feature. Between meetings I check Slack, chat with investors on WhatsApp and put things on a to-do list in Notion [note-taking software]. I snooze things to Saturday morning, when I’ll have a power session. I like to maintain Inbox Zero everywhere and keep up with all the Slack channels I sit in but reading everything is something I’m not going to be able to do for much longer.

13:30 Workshop with our creative and content teams and the marketing team, brainstorming improvements to our blog Method in Madness, which we’re trying to make into its own brand. I make coffee – try to get a latte heart – and flip through The New Yorker.

14:00 I block out an hour or two on Fridays for anyone in the company to book in and chat about whatever they want. Today a new manager asks, “What’s your take on the engineering team?” I’m as open as possible. We hire people who want to solve problems.

15:00 Walk around Moore Park West. The context-switching between product, marketing and operations is draining.

16:00 Weekly company demos in the lounge. The marketing team discusses an upcoming webinar, “How Lessons Learned from Our Youngest Users Can Help Us Evolve Our Practices”. Our in-house legal counsel demos the Ironclad tool that tracks customer contracts. The support team walks through a particularly challenging customer support ticket.

17:00 Friday drinks. Today there’s Mountain Culture’s Status Quo and Wayward’s Tropical Mango seltzer on tap, organic wines from Notwasted and a fridge full of Heaps Normal. There are lots of perks so another value is “Stay humble”. It used to be “Get over yourself” but no-one used that because it was a little aggressive.

19:00 Head to Oxford Street, Darlinghurst, for craft beers and pizza at Bitter Phew. Ideally, you work with people you can genuinely call friends. We have that, I think, at Dovetail.

21:00 I walk home, put on [rapper] Anderson .Paak, catch up on news on my phone, swipe emails then look at Instagram, LinkedIn and Hacker News.

Image credit: Nic Walker

23:00 Lights out. Put on my noisecancelling headphones and listen to ASMR [autonomous sensory meridian response content] on YouTube for 20 minutes. ASMR is an odd thing but it’s relaxing and meditative and it helps me with stress.

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