Dylan Trotter is a recent addition to Thumbtack’s Pro Tools team, where he develops the infrastructure necessary to build useful and reliable tools that help pros win customers on Thumbtack. The father of three (triplets!) sat down to talk about why he joined Thumbtack, the challenges he’s most excited about in this phase of the company’s growth, and how parenthood has shaped the way he works.
What does Thumbtack do, and what do you do at Thumbtack?
Thumbtack makes it as easy to get things done as it is to buy something on Amazon by instantly connecting customers with local service providers in their area. In order to do that, we need to convince a lot of pros to use our platform, which means providing value that they can see and understand. That’s where my team — Pro Tools — comes in.
We build tools that make it easier for pros to connect with customers, get hired, and be successful on our platform. Building this kind of software takes me all over the stack, from backend infrastructure to UI tweaks on the frontend. My goal within the team is to help provide the infrastructure necessary to build useful, reliable tools for our pros.
What were you doing before joining Thumbtack and why did you decide to join?
Before joining Thumbtack I spent seven years at YouTube where I led multiple teams, including the group responsible for maintaining the server that delivers youtube.com and YouTube’s APIs. After seven years, I was ready for my next challenge and Thumbtack stood out as a company with a lot of potential.
Thumbtack Engineering is at an especially exciting phase in its development — we’re large enough to have established good processes and engineering practices, but small enough to make decisions and build quickly. As an individual joining the team, you have a lot of opportunity to make an impact on the product, and the resources to tackle large-scale projects. And I really believe in the direction that we’re moving, where getting back to the customer is an instant experience.
What do you see as Thumbtack’s next big challenge?
With Instant Match, Thumbtack is dramatically shifting the way that pros and customers interact with the product — and this has major implications for the way the product works. If Thumbtack were a house, we’d be in the process of picking it up and moving it onto a new foundation. It’s a big challenge but an exciting one.
I think as a company our biggest challenge is to understand our pros — and the categories they serve — well enough to automate the process of pairing them to customers and to make it a seamless experience on both sides. We need to move fast without disturbing what’s already great about the product. From an engineering standpoint, that means designing systems that satisfy a broad set of requirements but are also flexible and extensible.
You have three small children. How has parenthood changed the way you work?
Parenthood changes the way you think about all your time and work is just one of the ways we spend a lot of it. Before I had kids, the line between my job and the rest of my life was blurrier. I would sometimes come into the office late on weekdays and other times work in sprints on the weekends. Concentrating for long periods of time on the weekends is much harder now that I have three young kids vying for my attention. In a lot of ways parenthood has forced me to use my time in the office more effectively.
Finding the right balance has been challenging but I’m lucky to work in an industry and at a company where results are more important than when you punch in or out.
What’s the last service you requested as a customer on Thumbtack?
This summer I hired a pro to clean and organize my garage. It was time.