Start-up Dovetail’s back-to-the-future view about working from home

Dovetail co-founder Benjamin Humphrey, who has more than doubled staff over the past year to 100 people, says he deliberately wants an ‘in person first’ approach.

Dovetail chief executive Benjamin Humphrey. Picture: Jane Dempster

Software giant Atlassian is on an aggressive ­hiring spree, offering a “work from anywhere” environment for its global staff, but one software start-up is pitching a very different culture.

Sydney’s Dovetail, launched five years ago by two former Atlassian employees, tells staff and new hires to be in the office most days: if they need to work from home, make it a Wednesday.

Dovetail co-founder Benjamin Humphrey, who has more than doubled staff over the past year to 100 people, says he deliberately wants an “in person first” approach.

He argues Dovetail’s policy is a point of difference in the war for talent in the global software business, where hybrid working or the “work from anywhere” culture has become the norm. Instead, he wants a culture based on the pre-Covid Silicon Valley of workplace bonding and collaboration laced with free coffee and Friday night drinks.

It is an approach, he says, that attracts young talented people who “self-select” to work in the office and be part of an ambitious start-up.

“We call it ‘in person first’,” says Humphrey. “We have an expectation – it’s not a rule, but an expectation – that people will be in the office four days a week on average.

“If people are going to work from home, it is agreed that Wednesday is the day to do that. So we’re all on the same page.”

Humphrey says Dovetail’s approach is attracting young graduates and more experienced people who miss the camaraderie of the office.

“We are a young company,” he says. “We care a lot about establishing the foundation for our culture which is a lot easier to do in person. A lot of people come to Dovetail for that culture.

“They are sick of companies which have gone ‘work from home first’ or ‘remote first’ because they miss their colleagues.”

Humphrey and co-founder, software engineer Bradley Ayers, met in 2013 when they joined Atlassian, the global giant founded by Michael Cannon-Brookes and Scott Farquhar. The US-listed business now has a market capitalisation of more than $50bn with a global staff of more than 9000. Atlassian is on a hiring spree, using its “work from anywhere” promise to boost its workforce to more than 10,000 over the next year. Its global goal is 25,000 people in four years.

Humphrey was lead designer with Atlassian in 2017 when he and Ayers decided to go out on their own, sensing a gap in the market for software that catered to collaborative researchers.

Like Atlassian, Dovetail has had global customers from its earliest days. The software en­ables teams to make sense of customer research data and insights in a collaborative, cloud-based platform.

More than 85,000 people at 3000 organisations – including Atlassian, Canva, Deloitte, Shopify and Starbucks – use the software to ­centralise, analyse, and collaborate on customer research data to improve the quality of their products and services.

Other customers include VW, Porsche, Gitlab, Cisco, Intel, Lenovo, SingTel, Weight Watchers, Shell, CBRE, Rockwell and State Street as well as Xero, MYOB, Bunnings, Australia Post, SafetyCulture and the ABC.

Some smaller Australian start-ups have ­struggled, forced to lay off staff in an uncertain economic environment, but Dovetail is hiring at least one new person a week, with offices in Sydney’s Surry Hills and downtown San Francisco.

The company has attracted the attention of overseas venture capital investors, who put in $US63m in January, valuing Dovetail at more than $US700m.

Cannon-Brookes is also an investor (through his personal company Grok Ventures) as is Australian venture capital company Blackbird. Dovetail’s investor and adviser group includes Stewart Butterfield, the chief executive of Slack; Vlad Magdalin, chief executive of Webflow; Daniel Yanisse, chief executive of Checkr; and US-based Felicis Ventures.

Humphrey says staff in other companies tell him they are often disappointed to find their colleagues are not there when they go into the office, hence his decision to make Wednesday the official work from home day if people want to.

Many employees are reacting to pre-Covid days when they were squeezed into office cubicles, forced to sit quietly in front of a computer, often without their own desk because of “hot desking”. They now argue that much of their work can be done from home without the time and cost of commuting.

Dovetail has a different view and takes a deliberate approach to the working week in the office: Monday, for example, is for meetings to plan work and welcome new staff.

Says Humphrey: “When a new starter joins – which is usually every week – we do a catered lunch on Mondays to welcome them.

“Everyone sits together for lunch, which makes people more welcome. It’s hard to do that kind of stuff ­remotely.”

Wednesday is usually more chilled, with some people working at home and fewer meetings.

Every second Thursday, it’s time for a town-hall meeting, with coffee and croissants and an opportunity for different teams to come together.

“One of our unspoken values is being highly collaborative and cross-functional,” says Humphrey.

“We don’t want to create functional silos. We don’t want the sales team getting grumpy at the marketing team or the marketing team getting grumpy at the product team.

“Bringing people together provides an ­opportunity for people to meet others across the business.”

Friday is when staff gather to talk about what they have been working on: “We crack open a beer and talk about the week,” says Humphrey.

It’s a casual event that turns into Friday evening drinks where people can invite partners and friends.

Humphrey concedes the average age of his staff, at 28, is probably younger than many other companies.

“We have a lot of people who are fresh out of university, maybe in their first or second job,” he says. “Their work from home set-ups are not very good. They are in shared flats. They don’t have dedicated offices or sit/stand desks. A lot don’t have air-conditioning. Over summer, their places can get uncomfortably hot.”

While it has an expectation staff will be physically at work, Dovetail also gives employees incentives such as “KitKat days” where they can take a break if they have been working hard. These include having an extra day over a long weekend. In total, Humphrey estimates, it adds up to ­another week and a half of leave.

He says: “Having an office to go to – a physical location – is a much healthier way to have a work/life balance. When I worked from home during the lockdowns, I always felt like asking: ‘Am I living at home and working or am I living at my work?’ If you’re in an office, work and home are separated, and when you are home you can switch off.”

Humphrey says he feels the people who have chosen to work at Dovetail share the same passion about having the company succeed as its founders.

“We are a scrappy start-up,” he says. “We are not an Atlassian or a Canva yet. We’re still trying to make it and drive towards success. We don’t want people with a sense of entitlement or complacency. We want people who have a sense of urgency and can bring that sense of ­accountability and rigour.

“We have a pretty lofty mission and we have a lot of work to do.”