Sentry’s David Cramer on bootstrapping a unicorn

Cramer: Performance for us was a natural extension of the space we already lived in. We envisioned connecting the dots to performance problems the same way we did with errors. While our performance product is still early days, we’ve seen great adoption already and are continuing to invest in it the same way we have for error monitoring.

When it comes to tracing, it’s our point of view that the industry has a long way to go before this data is easily utilized. Sentry has taken a cautiously optimistic approach to how it leverages traces, and instead of providing abstract trace analysis we use the data to create higher-level insights on their key transactions. This really is in line with how we have approached our product in general… focusing on curating an experience that resonates with a developer.

Tyson: Sentry is able to instrument a variety of languages and frameworks for automated error reporting.  I nerd out a bit when I see this.  How hard is it to encompass so many different technologies and keep pace with them?

Cramer: The open source nature of Sentry has always been great when it comes to supporting various technologies. When I started the project, I built the Python adapter myself, and very quickly we had third-party contributions for extending that to other languages. That still remains true today, though we employ a significant amount of both full-time employees and contractors to maintain and expand our ecosystem support. It’s certainly not a cheap endeavor, but for us it’s critical to our mission.

Tyson: You mentioned in this presentation (something I’d encourage anyone interested in CI/CD to watch) that you don’t have any human QA agents at Sentry.  I thought, really?!  How do you get to that level of automation? Is it still true today? 

Cramer: Yes, it’s still true today. We rely heavily on automated testing. It’s not perfect by any means, and we are continuously breaking our own product, but it’s optimized for shipping new features to customers as quickly as we can. It’s often ok—or at least tolerable—to have a little bit of breakage if you can also address that problem quickly. This is one of the key workflows Sentry aims to enable.

Tyson: That’s an interesting observation that by improving the customer feedback loop the QA phase can be less emphasized.

You have a background in infrastructure and devops.  Do you have a sense of where the industry is at in this story? How widely are best practices adopted?

Cramer: I think the industry is still all over the place. Forward-thinking companies are often experimenting while traditional enterprises are playing catch-up on whatever was hot two years ago. It’s probably in our benefit that not everyone is moving on the latest and greatest idea, as they often don’t stick. I do find that many companies these days have at least heavily invested into CI/CD pipelines in their organizations, which must be one of the most pivotal changes in technology in the last decade.

The bigger challenge we’re seeing here is how the increased presence of technologies like JavaScript are taking a toll on traditional DevOps orgs. It’s not a space they’re familiar with, so they’re still struggling to figure out how to support those projects. The biggest hurdle we see here are teams trying to utilize their traditional systems monitoring tools to monitor device-focused applications. One of the key reasons Sentry has become so valuable is due to the vast difference in development paradigms from typical infrastructure, and so part of our challenge is helping educate those teams that there is a new way to solve these problems.

Tyson: In a sense bridge the gap between app and system monitoring.

You pointed to frontend as a key area in 2019.  What do you see as the most interesting areas of activity in dev right now?

Frontend is still where we’re seeing the huge push in investments. A lot of the current approaches feel very experimental and are tough to see as maintainable, so there’s certainly still room for growth here. We try to be pretty agnostic about what’s happening as there’s typically a cycle in software infrastructure that repeats itself. The problems aren’t wildly different from a few decades ago, so we focus our efforts on the fundamentals of how software needs to work.

I think we’ll see the industry come back around over the next year or two to look more like traditional web development again, whereas today it’s very heavily pushing this CDN [content delivery network]-based static model. We’re already seeing a bit of this with some of the newer iterations including Next and Remix.

Tyson: In an interview with Insider a few years ago, you mentioned that early on investors didn’t really get why OSS [open-source software] is important to the business.   Has that changed?  Why is open source so important?

Cramer: In choosing to be an open source company, you’re choosing to support a community that believes in the right to learn and to share your learnings with others. This was fundamental to Sentry’s product growth and relevance. To this day we still have tens of thousands of businesses using our open source product and this will never change.

Tyson: As someone who really values the community aspect of OSS, that is very heartening.

You’ve gone through the venture capital fundraising experience. Do you have any advice for founders and startup people who are approaching that?

Cramer: Approach your business like it’s a consumer product, even if what you’re building is not, and if there’s value in what you’re doing you’ll figure out how to monetize it. Be committed in your belief of how to do something. We knew we had a great product, with a number of paying customers and a fair approach to pricing so churn risk was low. And that’s what our eventual investors bet on.

Tyson: That belief in your vision when it’s tested—that is tough!

You are very technical, but you’ve also dealt a lot with the business side.  Any advice for bridging the two worlds (especially for more tech-minded folks)?

Cramer: The most challenging phase for me was when Sentry hit mid-level maturity. We had a business, and the product was doing some great stuff and around this time; we had to build a go to market function. You know what you know, and know what you don’t know—and for me that was marketing and sales. I was actually anti these functions but now appreciate what they can be versus what they are.

I realized early on in my career my strengths and weaknesses and the business side wasn’t where I wanted to focus my energy. I want others to think about how do you add value in your day to day.

Tyson: That is so interesting and honest. I guess pulling in people who fill those gaps is key there.

I noticed on your LinkedIn profile you identified animal welfare and humanitarian relief as causes important to you.  Do you mind talking a bit about philanthropy?

Cramer: Philanthropy and giving back to the community is incredibly important to me and has been baked into the culture at Sentry. We invest in each employee’s philanthropic interests by matching employee donations up to $1,500 per year, per employee, to help support the organizations that matter most to them. Employees are also given 40 hours of volunteer PTO for community service a year. Additionally we are working on ways to expand these kinds of gestures into the open source community as well, where our goal is to enable our team to give back to projects they want to support.