the interview: Ashley Smith

Ashley Smith is a prolific angel investor, board member, and advisor to startups. Prior to pursuing investing full-time, she held senior marketing roles with companies such as Facebook, Google, GitLab, GitHub, and Gatsby.

You’ve played a significant role at a number of high-profile companies including Twilio, Facebook, Google, GitHub and GitLab. How did you refine your understanding of what an ideal role looked like for you?

I think everyone’s ideal role changes with time and frankly, an ideal role can be hard to find. In retrospect, each role I took was me looking for the next progression in my career. I was always looking for greater responsibility, more opportunities to learn, an awesome team, and high growth potential. Checking all of those boxes is a lot to ask for but I got lucky quite a few times to have all 4.

When I got my first startup job at Twilio, I simply wanted a job in tech. When I took my next role at Parse, I was looking for a leadership opportunity and another small, brilliant team like my team from Twilio. Each job I took after that I was looking for another thing that would push me forward in my career.

I think the key here is figuring out the one thing that will push your career trajectory along and just go after it. For me, I was able to figure this out along the way by asking friends and people in the tech community that had been on this journey before, and I don’t have any regrets about any of the new roles and companies that I’ve joined.

It seems like you’ve really honed your focus around companies that cater to developers. What excites you about building and advising companies in the space?

I love the developer audience. I started coding really bad websites when I was 12 and have been pretty obsessed with computers and technology since my elementary school got our first Macintosh. As a kid, the internet totally changed my world, and it has been an obsession of mine since I first got access. I am lucky that I somehow ended up working on the things I’ve been obsessed with since childhood.

I love how quickly the developer tool space moves and how a developer can build something really interesting, open source it, and then it’s quietly running on every device on the planet because some other developer liked the software and used it in their project.

The best products, projects, and tools in the software world are the ones that are really well built and that people love to use. It’s all about good products and experience, and less about traditional marketing which I absolutely love.

Because developer tools tend to follow a bottoms up adoption pattern, companies in that category rely heavily upon marketing for demand gen. What marketing tactics have you seen developer tools companies employ successfully vs. unsuccessfully?

Without a good product, marketing for a developer tool is pointless. Even with a good product, I think it’s a non-traditional style of marketing that actually works for developer tools. I’ve seen everything work and nothing work, and it all really depends on the community built around a particular product.

I think it all starts with community building and finding ways to get people talking about what they are working on using your product. Figure out how to amplify your users’ voices to other people that could be using your product, and you’ve got a nice start. From customer stories to really great technical, community-driven content to online community monitoring, everything contributes to helping build out a strong community around your product.

Make sure to have a great website that gets the right people the things they are looking for. Individual developers want documentation and an easy way to get help. Teams of developers want to figure out how to onboard other people and how to get the rest of their team to want to use your product. When your product is being used in a larger organization and you’re dealing with enterprise buyers, they really want pricing and general knowledge of why this particular tool is best as opposed to another tool.

A big thing I see founders miss is being able to clearly talk about what they are building. If your product is so complicated that I can’t figure out exactly why it exists and how it’s helpful to my work within a few scrolls, figure out how to explain your product’s value more succinctly.

You’ve also spent a lot of time in and around open source. What are your thoughts on open source as a distribution strategy and as a business model?

Open source is so awesome. Like I said earlier, just the concept that a developer can contribute to a project and that contribution ends up in every device on the planet is so cool. If you’re building open source tools because you want to build cool stuff that people use, awesome. If you’re simply trying to make money, it gets a bit more murky.

I’ve had a lot of companies come to me and ask me if they can retroactively open source some part of their product to help build a community around it. The other side of that coin is open source companies who are trying to find a way to monetize without ruining the community they’ve built around a particular tool while simultaneously still being able to afford to maintain the tool.

In a perfect world, we can balance both open source as a distribution and monetization strategy, but it can be hard to get it right. I absolutely love seeing companies pop up that seek to monetize through open-core, support, hosting, etc. alongside or on top of a really good open source project. It can mean guaranteed maintenance for the project, some super great features, and more community support for a tool people are already using. The downside can be when previously open-sourced, free features are turned into paid features and the company has to figure out how to do a smooth rollout of the changes. My advice here is to figure out what features people will pay for that cater to teams or enterprises, build them, and charge for those. Don’t force people to pay for basic functionality features that are helping grow your adoption. Again, it’s a hard balance.

Besides the increasing emphasis on open source, what other trends in developer tools are you most excited to see play out in the next five years?

I think helping developers work together more efficiently will continue to be a big part of new tools we see popping up. I think making ML, AI, and data tools more accessible and easy to use for software developers will continue to be a trend. I still think it’s too hard to get a production environment running on a computer, so I hope someone solves that. In general, going from hacking around on your machine to live code is still pretty complex. I think everyone these days is starting to interact with engineering teams at work more which can get complicated, so I think we’ll see a series of products helping marketing, sales, support, and customer success to work more easily with engineering teams. I think we’ve barely scratched the surface of testing.

When Buildkite raised its Series A round, you joined as a board member. What have you learned from being a board member on the other side of the table?

I love the Buildkite team and was so excited to lead that deal and get to join their board. They are really building an extraordinary product for development teams that need lightning-fast testing and delivery and after speaking with Buildkite customers pretty often, most tell me it is their favorite developer tool in their stack. What I was getting at with my earlier comment about barely scratching the surface of testing is partially due to what I’ve seen coming down the pipeline from the Buildkite team and partially due to seeing so much buggy software make it to production.

What I’ve learned is less about Buildkite specifically and honestly is more of what I’ve seen from observing boards on both sides of the table over the last decade or so. My biggest takeaway being in board rooms as an investor instead of as an executive team member is that investors are humans that make mistakes but generally, they’ve seen and solved exactly this problem that any company is facing at any given stage. If they haven’t solved this exact problem, they have access to someone that has. Take the intros.

It’s hard to take advice from someone who isn’t in the business every single day, but realize other people have solved this challenge before — other teams have survived growing from 10 to 100 people, other marketing or sales executives have failed to hit their numbers. Listen to the advice and try to incorporate it quickly. Otherwise, in most cases, it will take you nine months to a year to reach the same conclusions that your advisors highlighted to you in the first place. You likely took investor money so that you could add expertise around the boardroom table, not solely because you needed capital.

I think most problems fall into a few categories (outliers aside): adoption/growth is slow, product/engineering isn’t shipping, marketing/sales isn’t hitting targets, or the executive team has dysfunction. Most investors have dealt with all of these either as a board member or as an operator. Take their advice and act quickly.

While you’ve invested on the side for several years, you recently left the world of operating to pursue investing and advising full-time. How did you decide that it was time for you to make the switch?

I get bored easily. Anyone that has worked with me, for me, or tried to manage me will confirm. I find that with investing and advising I’m solving problems and helping people build their businesses without getting too in the weeds. For me, it keeps it interesting. To be clear, I get very in the weeds when a big problem pops up and I can be helpful, but for the more mundane day-to-day, I’m useless and I know my limitations. I’m still committed long-term to the companies I advise and invest in, but I’m not expected to show up to all hands. :)

Operating was wonderful for a long time and I love the people I’ve worked with and the products I’ve worked on, but it was time for a change. Investing makes me super happy. I love working with founders and helping them build good products and great companies.

Connect with Ashley on LinkedIn and Twitter. Join the table, a community highlighting women in enterprise and deep technology, to receive interviews, insights, and resources right to your inbox.

Know someone building an exciting new company in dev tools? Get in touch @ brittany@crv.com.