When To Jump Ship
VC is a game of patience, but it's likely you won't spend your entire career at one firm.
Venture Upward is a field guide for surviving, getting ahead, and succeeding as a venture capitalist. Created by David Beisel (@davidbeisel) and Rob Go (@robgo), it's written for non-partner VCs working their way through the ranks.
If a key guiding principle for a successful career in venture is to not lose your seat, then there are a number of ramifications, the first of which is how long to stay at your current firm and when to leave.
The overarching framework for venture career planning is actually similar to how a startup should approach fundraising — the time to explore making a move is after a key milestone. Just as a startup’s best time to fundraise is after a key team member joins, a strong customer win, or achievement of salient top-line revenue figure, the right time to explore thinking about switching firms is after notable career inflection points such as recent sourcing success, actually getting board seats, a significant startup funding milestone of one of “your” companies, and of course, positive exits. Recent points on the board give you more credit, so to speak, to leverage into a better role/title/compensation-level at another firm. These achievements signal to a potential new prospective employer that you’re truly looking to trade up, rather than soon being escorted out the door because of underperformance.
That being said, recently passing a career gate doesn’t doesn’t mean you necessarily should switch firms. Rather, you should explore if it’s the right thing to do. There are numerous costs associated with switching platforms — re-establishing credibility with a new set of colleagues, starting over with your body of work of startups which you’ve worked with. Plus, there’s always uncertainty around the devil you don’t know.
Accordingly, there a handful of questions to ask yourself when considering changing funds:
Is your current firm on the rise? Fundraising cycle timelines and fund sizes are the best (though not 100% correlated) proxy to performance and medium-term prospects of the firm. Like in startups, a rising tide lifts all ships. Growth creates opportunities. A fledgling firm in its first one or two funds may take too long to start to bear fruit for junior employees. Or a legacy heritage firm may be a lucrative endeavor for the GPs running it, but stasis leaves a zero-sum game for all of the remaining players.
At larger firms, has there been a demonstrated path towards a partner role with colleagues one or two steps ahead in their career? Evaluate how challenging it has been for your colleagues to navigate the power dynamics in your firm or if there’s an apparent ceiling for upward mobility. (Raw title obviously matters, but in a future post we’ll look to uncover the opaque power ladder in venture firms.)
Are you empowered to build a track record worth pointing to? Are your senior colleagues allowing you to take credit for the contributions which you’re making? Are you stepping up to lead deal processes, attending board meetings, becoming an official Board Observer when appropriate and applicable, and/or serving as an actual Board Director? Or instead are you being treated as a sourcing machine and with little responsibility subsequently.
Do the kinds of deals the firm does complement your long-term interests? Because venture is a long path requiring dedication, this question about deal fit and next #5 point to the longer-term viability of the situation you currently have in place. It’s great that you were able to break into venture however you did… but it’s also worth considering whether the stage or focus (b2b, consumer) of your present fund aligns with your real interests. The longer you focus on one stage or category, the more expertise and related network support you develop, and the more difficult it becomes to change. Career inertia is really hard to alter.
Can you actually see yourself working with these people for the long term? This is an obvious but under-discussed question. I have friends in the industry who spent years clawing their way up to the top tiers of their VC firms, only to finally appreciate that they didn’t like the people they’re surrounded by. I find it difficult to believe they didn’t harbor those same doubts a decade earlier, but instead suppressed them. Life is too short. Find people who you want to spend most of your waking hours with. And if you can’t stand your teammates, move on.
While all these questions bear consideration, it's worth underscoring that if your current seat becomes in jeopardy for whatever reason, you have a clear signal that it's time to leave. A lateral move when even when the timing isn’t optimal is much better than getting sidelined from the game altogether.