Get to Know: Glen Oakley, Site Reliability Engineer
When Glen Oakley joined Thumbtack right out of college in 2014, we had fewer than 20 engineers. Three years later, there are more than 100. In this interview, he talks about the challenges the Site Reliability team is tackling, his move from software engineering to site reliability engineering (SRE), and why he’s pushing his teammates to try circus arts.
What does Thumbtack do, and what do you do at Thumbtack?
Thumbtack is a marketplace connecting local service professionals and customers. If you’re looking for a plumber, for example, you’ll be prompted with brief questions about the service you need — Is your toilet running? Is your sink leaking? Then you’re connected with professionals who best fit the job.
I’m on the Site Reliability team, which works on the infrastructure that supports our products. I’m mostly focused on helping the people who develop our features, so in a way, my customers are other engineers.
What kinds of problems does your team solve?
A lot of what we do is try to anticipate what the rest of the Engineering team will need. If we expect they’ll run into trouble with things like storage or application deployment, we’ll find and test a solution, and iterate from there.
For example, we recently expanded the way we use Elasticsearch. We’d already been using it for log processing, but then teams started to have more needs that PostgreSQL didn’t meet. So we did some testing to make sure Elasticsearch would fit the bill, and then we exposed a separate Elasticsearch cluster. People seem to like it so far.
What other problems have you tackled recently?
We had a big one around application deployment. We’d been on Amazon Elastic Beanstalk for a long time, and we wanted something more Thumbtack-specific that could work more easily with our build systems and monitoring tooling.
So we built our own wrapper around some other Amazon services and Docker containers. Now there’s a simple command-line interface where an engineer can say, “Hey, I want a new application,” and “I want the application to be a recurring task,” or “I want it to be a web server.” From there, it’s easy to edit code, wrap it up in a container, and deploy it for either staging or production.
You joined Thumbtack right out of college. Why did you choose to work here?
I first heard of Thumbtack at a conference hosted by Sequoia Capital, and they stood out from all the other startups there. Thumbtack was the one solving a real, meaty problem, not just inventing some new convenience. I saw it as an opportunity to help people — and not just people who love tech, but people who maybe hate tech or worry it’s going to kill their businesses. Thumbtack actually helps build those businesses. The idea of working on that was exciting.
How did you end up on the Site Reliability team?
When I joined Thumbtack, I was on the Marketplace team, which at the time was focused on making sure requests went to the right professionals. We only had one site reliability engineer back then. But I’d done a couple of internships focused on infrastructure — at Merrill Lynch, and at a hardware startup called Nebula — and I knew I wanted to work more on that level than on product features. So when the time came to grow the SRE team, I decided to join. And it turned out well — I really like the work I’m doing.
“I saw joining Thumbtack as an opportunity to help people — and not just people who love tech.”
We need to keep growing, so now we’ve started an internal hiring program where people can do a six-month trial on SRE. If they like it, they can stay; if not, they take some site reliability knowledge with them to another team.
Is it common for engineers to switch teams at Thumbtack?
We have a lot of flexibility. If you’re not doing work you see as impactful or that you’d use to further your career growth, you can switch. It all depends on what you want to do. And recently, we’ve started to define our engineering roles a bit more. Before, pretty much everyone was just a software engineer, but now, we’re laying out multiple paths. You can focus on a specific technical area, or you can work toward managing others.
“We’re laying out multiple paths. You can focus on a specific technical area, or you can work toward managing others.”
The combination of role definition and flexibility is super helpful, especially for people who are still figuring out what they want to do. Personally, I’ll probably stay on the individual contributor path, because I just love building stuff. I even do it in my free time. I’m addicted!
Speaking of free time, do you see your teammates outside work?
Yes! Our teams in Engineering are pretty small, and you get to know people both personally and professionally. Thumbtack also has a lot of cross-department events, so we meet people outside Engineering too. Happy hours are pretty popular, and a bunch of groups have formed for things like sports and gaming. I do circus training — acrobatics, aerial, stuff like that — and a couple of us are trying to get a club together for that.
Cool! Besides the circus training club, what makes Thumbtack unique?
One thing I really like is that our teams are fairly independent. We have company-wide goals, but it’s up to each team to decide on the projects that will have the biggest impact on those goals.
We also really value transparency, almost to a fault. You have to learn to filter and prioritize your emails because so much is shared, but it means there are no surprises. I feel more engaged with the company because I’m completely up to speed on what other teams and departments are working on, what the Coordination team is thinking about, and where we might want to go in the future.
Interested in learning more?
Check out open roles or get in touch at recruiting@thumbtack.com
