Dovetail · Benjamin Humphrey

Benjamin and his co-founder Bradley solved the problem of collecting your customer's research and built Dovetail.

June 13, 2022
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Table of contents

  • Dovetail
  • Founders - Benjamin Humphrey and Bradley Ayers
  • Offices in Sydney and San Francisco
  • Started in 2017
  • 2 founders & 70 employees

Benjamin, what's your backstory?

I studied Computer Science and Design at the University of Otago but never graduated. Instead, dropping out after two years to join a small web design agency as a designer. I then worked as a Product Designer for a company called Avos and then joined Atlassian. I spent four years at Atlassian as a Product Designer, working my way up to Lead Product Designer and eventually leaving to start Dovetail.

Tell us what your company does?

We're a software company that builds tools for other businesses to help them develop and service their customers better. Specifically, we build software so that everyone anywhere can make sense of their research.

How did you come up with the idea?

The name 'Dovetail' stemmed from a guy I used to work with at Atlassian called Alastair. He used the verb 'dovetailing' a lot in the context of dovetailing raw data from research into insights, the coming together of two things. I thought that was nice and quite liked that it can also be interpreted as an elegant woodworking joint that doesn't use glue or nails. I looked at lots of different names from a practical side and chose something that was easy to pronounce and spell!

How did you go about building and launching the business?

It started when I worked at Atlassian on this diary study project, which is this longitudinal research method where you ask participants, usually every day, to write a journal entry, just like a diary. I partnered with a researcher who had a very convoluted process for collecting these journal entries. She took all the content and printed it out, manually highlighting everything on a whiteboard and literally cutting and pasting snippets to create a physical affinity map. The whole process took around three months, but the diary study itself only took two weeks.

I saw this huge gap in creating better software for researchers. At the time, I was a designer, and Sketch was replacing Photoshop as the hero product for visual design. It was clear to me that designers needed something like this. So the first version of our product was an email and SMS interceptive surveying tool where you would set up a schedule with your research participants.

You would get an email or a text message throughout the day that you could respond to. And the whole concept was called 'interceptive texting', which is actually used by market researchers and researchers around the world. Within about six to nine months of working on our first version, we had some paying customers, which was great. But after they finished their project, they would cancel because there wasn't any long-term value in storing their data and continuing to pay for it. When Brad joined, we talked to our customers to figure out what was happening. They showed us what they did with their data after downloading it from Dovetail, which was a weird and wacky analysis. And so, we pivoted to create a new version of Dovetail to hold and analyze data, which is pretty close to what we have today.

How have you grown the business?

Brad and I didn't raise money for nearly two and a half years because we had enough savings thanks to our previous jobs at Atlassian. So I suppose that Atlassian's success and the two of us working there was a lucky break. I think many other founders don't have the luxury of being able to bootstrap for as long as we did because they obviously have to pay their own salaries and don't have heaps of money lying around.

Another lucky break would probably be getting onto video as early as we did. When Dovetail launched our video transcription feature, I think the team was maybe eight or 10 people. Our small team of engineers essentially built YouTube for transcoding videos.

These videos were turned into different resolutions, streamed back, and then we partnered with Rev to do the transcription. Adding all of that to Dovetail was a fair amount of work, and I was very sceptical at the time about whether we could pull it off, but we did. And it's a good thing we introduced it that early since our video transcription feature is something that really took Dovetail to the next level.

What's your biggest selling product/service?

Markup is our most popular product. It helps transform raw data into insights. Its versatility means that anyone, including researchers, designers, product managers, support people, and marketers, use it. We currently have 3,000+ paying customers and 45,000+ users around the globe.

What have been some of your biggest failures along the way?

We've made a lot of product decisions that were not optimal. We have more opportunity cost failures rather than massive failures like almost going bankrupt or something like that. Another failure I'd say we learned from is not being tight enough on our values and culture interviews in the early days. We learned the hard way the cost of having someone that isn't the best culture fit. It can bring the whole company down and really tank morale if you even have a few negative people. So after making that mistake, we've really tightened up our interview process and Brad and I still interview every person that joins Dovetail, which has been really positive.

What digital tools do you use regularly?

We're big Slack users, both internally and externally, for our Dovetail community, which has over 4,500 members. Aside from that, we use Slack and Zoom for communication, Google analytics to measure results, Figma for design, and Notion for planning. We obviously use Dovetail for our own research and to get closer to our customers, too.

What books have been a great inspiration to you as a founder?

I'm not very good at consuming media, but I like reading startup books because there's a bit of drama, and there are obviously some business lessons. I recently read Super Pumped by Mike Isaac, which is about Uber, Bad Blood about Theranos, and I have Hatching Twitter on my desk at the moment, which is about Twitter's origin story. I like that sort of content because they tend to be page-turners like a fiction book, but it's based on fact and has some relevance in there for running a company.

Any podcast/websites that help you run your business?

When flying back and forth between our Sydney and San Francisco offices, I've listened to the Darknet Diaries podcast by Jack Rhysider. That's been interesting to tune into the abuse around technology.

I love reading print, and I used to read The New Yorker every week in the first three years of Dovetail, which was great but overwhelming and difficult to keep up on a weekly basis. Besides that, I read a lot of articles written by my executive coach, Ed Batista. There are a lot of valuable nuggets in there that I often share with the leadership team and the Dovetail team at large. I also read a bunch of other random technology stuff on an ongoing basis, like Hacker News and Reddit.

What quotes do you live by?

At Dovetail, our ambition level is very high, and we tend to ship things faster than other companies because we don't constrain ourselves to the team size we have. We have a saying - 'anything is possible. And I think we live up to that.

"anything is possible"

What do you do to look after your mental health as a founder?

For me, one of the key things is lots of sleep. I have invested in things like dark bedroom shutters and ear plugs, and I try to go to sleep at the same time every day. I don't think people understand the ROI of sleep. If you get a good eight or nine hours compared to six or seven, the eight hours of work you're going to spend at the office that day will be so much more impactful just from another one or two hours of sleep. Your decisions are going to be that much tighter. You'll have much more clarity and concision when you're context switching between meetings, which I need to do a lot.

I started running as well. I never thought I'd be a runner since I used to hate it and exercise, in general, in high school, at university, and even through my twenties. But I've found that if I go for a run at the end of a busy day, it clears my head, and I feel better for it. I've also gotten to a point where I actually enjoy running itself along with the outcome, which is good. I'm also trying to play a bit more tennis and eat healthily.
Another skill you have to get good at as a CEO is pushing accountability down. What I'm trying to work on at the moment with the leadership team is driving accountability with them and pushing the stress down to them as well. You hire senior people because they're good at their job. They also bring a huge amount of value because they can handle stress and not buckle under the pressure of a scaling startup.

In a few words what does it mean to be the founder of a business?

It's complicated and hard. There's a lot of pressure to continue to grow as the company grows, so you need to always have a growth mindset. You need to almost 'fire and rehire' yourself every few months to keep up with the changing requirements of the business. There's a lot of context switching on any one day. I might have back-to-back meetings where I give product feedback to a product manager. Deal with a leadership team conflict. Interview a creative director candidate. Talk to a journalist. Write a blog post. Review a marketing project. Pair with a designer and prepare slides for the next company all-hands. The context switching is very draining and something you need to get really good at.

What are the biggest pieces of advice you’d give to other founders?

The main thing in the early days is getting in there and getting stuff done. I think many founders and maybe investors in early-stage companies spend too much time strategizing. Dovetail is now a 70-person company making a fair amount of cash every year that's responsible for ~$65 million in the bank. So fairly legit. But we never had a business plan, barely a pitch deck, and didn't even have a budget or an annual operating plan until last week. Whereas I see founders who haven't got a product, they've put together an annual operating plan with expenses down to the smallest detail. But it doesn't really matter if you don't have a product because if you don't have that, you don't have any customers, no business, etc.

Where can people find out more about your business?







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