Former Dropbox CTO Quentin Clark just joined General Catalyst as a managing director

Quentin Clark resigned a couple of weeks ago as the CTO of Dropbox at the same time that the storage company announced two other execs — Bharat Mediratta and Tim Young — were joining its leadership team in Clark’s stead.

Now we know where Clark was headed — into the world of venture capital and, more specifically, into a role as a managing director with the 19-year-old venture firm General Catalyst.

He joins a team of enterprise investors within the firm that includes Steve Herrod, himself the former CTO of VMWare; Paul Sagan, the former CEO of Akamai; and Holly Maloney, who joined GC as its first female managing director roughly two years ago after spending seven years with North Bridge Venture Partners in Boston. Clark will remain in the Bay Area, looking at earlier-stage opportunities alongside Herrod, while Sagan and Maloney handle later-stage deals from GC’s Boston location.

To find out a bit more, we talked late last week with Clark — who’d previously spent two years in the C-suite as SAP and 20 years with Microsoft before that — to learn why now is the right time to become an investor, and what he’s particularly interested in seeing.

TC: You’ve worked informally with GC for a number of years. Is that right?

QC: Yes, I was in Seattle for a long time. I moved down here five years ago and was introduced to a bunch of great folks in the venture community, including Hemant Taneja [of GC] and Reid Hoffman and I spent time with different investments in their portfolios, helping to advise them and investing and that kind of stuff. After I left SAP [in August 2016], I spent a year with GC engaging with a bunch of things in its portfolio.

TC: So becoming a VC was something you were considering.

QC: It was something I was considering long term, but Dropbox gave me this amazing opportunity to join them in this operational role that I couldn’t turn down, and working with [CEO] Drew [Houston] is now one of the highlights of my career.

TC: They must be very different, Dropbox and SAP. How would you characterize your experiences inside both companies?

QC: It isn’t often you get to help pivot something as impactful as what’s happening at Dropbox. We did [Dropbox’s] User Conference [event in late in September],  and we launched Dropbox Spaces, which is a fundamental pivot based on a point of view about what the workplace is like and where the pain points are, and you don’t get to do things like that very often. The last time I got to do something that significant was at MIcrosoft, migrating from on-premises to Azure and rebuilding the entire product portfolio to be entirely cloud based.

To have your hands that deeply in the work is rare. At SAP, it’s very, very large organization, with a very large portfolio, and you don’t personally dig in that deeply in terms of your ability to take an individual product and [change it into something else].

TC: How long ago did you start investing?

QC: I wasn’t investing at Microsoft. There’s now a bigger much bigger tech scene [in Seattle] than five years ago. I really started exploring when I moved.

TC: You’re now going to be working as an enterprise-focused investor. But what, more specifically, interests you?

QC: I’m interested in healthcare. I’m interested in how people navigate their careers. But mostly, I’m business-to-business focused. I think the next generation of enterprise software will help people excel in the work, though machine intelligence, the cloud, the evolution and maturity of the devices we carry.  I think this wave we’ve seen with the consumer space will impact the enterprise space more deeply, so I’ll be looking for larger-scale impact on how people [manage] their day to day.

TC: Are you at all nervous about getting up to speed?

QC: I feel very well-supported. There’s a lot of teamwork at GC, so they won’t leave me out there to do this myself. This is literally a venture business, though. I am going to make decisions that 100 percent of them won’t pan out, but that’s part of finding success. My hesitancy will be around whether I’m investing enough, not whether I’m investing in the wrong things — at least, initially. But I do have 25 years of judgment that I can apply. I’ve been making investment choices in my career for a long time and seeing bets through and making them successful. That gives me confidence that I can exercise good judgment in this new role, too.