Bigger isn’t better: what it’s like to be an engineer at Dovetail

Hi, I’m Blake. I joined Dovetail after about six years in the software industry; three years as a developer and three as an engineering manager. I’ve been in a mix of teams and roles over my career, but what I love about work is improving customers’ lives through software, so I often end up in product teams. In my spare time, you can find me at the arcade tearing up the rhythm games, watching anime, or enjoying a whisky tasting and pretending I can tell the difference.

What is this?

This blog is a high-level reflection of my six months at Dovetail after leaving a mammoth technology company. Like loads of my mates here, I left a big company to join Dovetail. You should read this if you’re interested in my authentic take about the differences between a big company and Dovetail after six months or considering a similar change yourself.

It certainly wasn’t an easy decision, but it might’ve been easier if I had more information or some opinions from people who’d done it before. So buckle up; that’s what I’m offering you today.

Push and pull forces

For me, a significant source of pain was feeling frustrated with the inability to change things at a big company. The day-to-day had gotten so process-heavy that I had lost a lot of my autonomy. Changing things was daunting, not motivating. You’d also hear other folks say that they’ve felt the culture steadily declining, or they’re struggling with career growth in their current role.

These are all push forces. They’re pushing you away from your current position. They’re useful for identifying what you’re unhappy about but focusing on push forces alone will not help you find a meaningful change.

You’ll also need to weigh up pull forces—what attracts you to other options—to make the best decision.

Pull forces of Dovetail compared to a big company

This might not apply to everyone, but reflecting on my first six months, these are the things that I think have been the biggest “pull forces” of Dovetail compared to a big company.

The high velocity of changes

This one is probably not a surprise. Yes, I can confirm that you can get things done faster without the burden of a dozen dependent teams, changes needing to be planned a quarter in advance, and an uncomfortable amount of distinct codebases and services.

You’ll typically own features end-to-end at Dovetail, compared to a slice of a feature in a big company. Fewer dependencies mean you are empowered to (and expected to) get your hands into all parts of the codebase and across the whole architecture to get things done. We deploy daily and seeing our internal changelog each deployment is baffling compared with my previous teams.

Our hackathon, Make It, ends with things actually shipped. This makes the ritual much more meaningful and fun.

It’s super motivating seeing what everyone’s achieved at weekly demos. This one was an unexpected delighter for me. More changes means demos are more interesting. Also, since demos are company-wide, getting an insight into what’s going on cross-functionally is really neat to see.

The quality bar is very high

A Product Designer founded Dovetail, and it shows. The culture of quality, from sweating the details on margins to religiously ensuring UX makes sense as much as possible, has transformed me as an engineer.

I’m a better engineer thanks to the quality culture. At my last job, it often felt like the goal was to ship the bare minimum as close to the target date as possible, probably due to more dependencies, stakeholders, and deadlines. Working at Dovetail has rewired my brain to place more of a focus on quality. I like this because I’d rather be an engineer more skilled in building a high-quality product than skilled at whittling scope and hitting deadlines.

Everyone maintains the quality bar at Dovetail. I’ve seen the engineering, support, marketing, and revenue teams all have input and display a sense of ownership of the customer experience—not just the designers and product managers.

Everyone has customer empathy. It wasn’t easy to talk to customers at my previous company. User researchers, often your only direct line to the customer, were few and overloaded. Getting involved in research was a chore and self-driven. At Dovetail, we use our tool internally, spend time on support, and lurk in our Slack community, which builds a lot of customer context and empathy—driving quality.

The codebase has scaled surprisingly well

Given all the junk I just said about shipping quickly, you’d expect it to be “scrappy central” over here, but no. Far from scrappy, the codebase has scaled with a 3 to 4x increase in engineers without falling over. Getting a dev environment set up remains super simple, and our robust typing system makes it easy to get familiar with. I spent a lot of my time working around legacy code at my previous company, but that’s just not a thing that happens at Dovetail.

The team is really good

A lot of companies say they hire the best. One thing that I think stands out about the Dovetail engineering team is the breadth of skills. Because of the expectation to own features end-to-end, the engineers are exposed to a wider variety of technologies. They have a broader understanding of systems than engineers on other teams I’ve worked with.

The broad skillsets, combined with the customer and design-led culture, make the team highly effective engineers. It’s a team I’m incredibly proud to be part of.

Across the company, another thing I really like is that we celebrate individuality. Being a smaller company, we all know each other, and the team is wonderfully accepting. You can see our values embodied every day—my favorite practical value is “Do the thing.” I think it tempers our quality obsession with a deeper level of pragmatism.

It’s refreshing to have delighted customers

Another surprising delighter for me was the experience of telling people where I work. “Whoa! I LOVE Dovetail!” feels much better than “Oh, you work on <big slow product>...<avoids eye contact>.”

Does this resonate with you?

Well, you’re in luck. We’re tripling the engineering team over the next year. Come and be a part of the journey and delight customers, work with some of the best, have the type of impact you’re looking for, and become the best engineer you can be. Check out the careers page for more information.