Thinking About Proximity and Optimization in a Job Search
If you’re in venture capital and you’re trying to make partner somewhere, should you get some operational experience somewhere and then come back? It’s a question my VC coaching clients ask all the time.
Yes! 100%.
You should be like Sarah Tavel. You should source Pinterest while at Bessemer, then “[join] as a "utility player" before we had product managers, and [become] the first PM at Pinterest.”
That will lead you to ultimately become a Partner at Benchmark, one of the top venture capital firms in the entire world.
Easy peasy.
Of course, you just have to find the next Pinterest, which IPO’d for $10 billion, but that’s just a small detail.
Clearly Sarah thought the team and the product at Pinterest was special, but so does every VC who does a deal. You wouldn’t try to convince your firm to write the check if you didn’t believe that the company had that kind of potential—but clearly they don’t all make that leap.
After my time as an Analyst at Union Square Ventures, I made a similar leap to what was, at the time, an agency services company trying to become a product company. I also became their first consumer “product person”. They had a tool for creating virtual characters when Second Life and virtual worlds were a hot space—14 years before Facebook changed its name to Meta to signify the seriousness in which it was approaching this very thing. Clearly I imagined the potential of this space to be just as big as Mark Zuckerberg imagined it to be when he changed Facebook’s name and sunk nearly $50 billion into it. I’m sure we were both just as confident in it as Sarah was in pinning, yet she’s the only one of the three of us ever to make a dime from our investments of time and money.
Similar to Sarah, I was in close proximity to this company and despite my lack of a product background, built a close enough relationship to them that I convinced them I’d be a good fit. That happens a lot to folks coming out of VC—where you might not be the best fit on paper, but you have an inside track to a job because of a trusted prior relationship.
Outside of VC, it happens, too. Nearly everyone has struggled with the question of whether you should take this job that is in close proximity to you because you know the team, or market, or you know you can do it versus doing a much more comprehensive search to try and optimize.
Even outside of job search—this happens in life, be it in finding a partner, buying a home, etc. When I bought my first apartment, I chose a neighborhood that I knew really well, but not a particularly “risky” one that would have had higher price appreciation potential—something that should have been a consideration for me as a 25 year old single guy. I went for “safe and cheap” when “cheap, but with high neighborhood upside, should have been the criteria.” I fixed that problem later when my wife and I got our current place—selecting a few specific criteria I wanted to optimize around within our budget after watching the market passively for a while. I wanted to be near a park, near an express subway, with an efficient layout, with lots of windows. It was pretty clear that, within our budget, we weren’t going to get better in any one of those categories than what we found.
I asked some friends that have made consisitantly strong and seemingly thoughtful career moves how they thought about these kinds of decisions.
Camille Fournier, former chief technology officer of Rent The Runway, former vice president of technology at Goldman Sachs, and author of The Manager's Path had a particularly interesting take:
“If you're employed already, it's easy to confuse the realization that you need a new job with the idea that you need this new job. It's one thing to take casual conversations with recruiters or companies. When you find yourself going to several rounds of interviews and having serious conversations, I tend to think that the signal you're getting is that you need a new job. It might be this job, but it's probably a good idea to talk to a few more companies before just jumping on the first opportunity that caused you to realize it's time to move on.”
Yuliya Mykhaylovska, who worked at leading venture capital funds Greylock and Lerer Hippeau, pointed out that one of the reasons why this happens is because an opportunity that falls in your lap often gets out ahead of something that you source on your own out of a more intentional process:
“…The most crucial part of a job search is the start, when job seekers should carefully and clearly set up the conversations to get the "flywheel" of opportunities in action. Setting up the foundation of that flywheel is heavy lift up front, but then the results come 2-4 months after you share your intentions with your network and get the flywheel going. First and foremost, it's important to define what it is you're looking for and what you're not looking for. Many candidates, especially ones more junior in their career, reach out to their network with vague notions of what they're hoping to do next; in a world where professionals are super busy and in the midst of dozens of to-do's, vague asks get lost -- specific asks get answered.”
The idea that “optimized” searches take some time was echoed no matter who I asked—especially given the important role that networking plays.
Jessi Hempel, Senior Editor at Large @ LinkedIn and host of the Hello Monday podcast, shared that the pull towards safety can be strong:
“I think I have always held out for the roles that have a strong intuitive pull. And I have tried never to go backward. To me, backward simply means doing something I am positive I can do because I have done it before. There are times I have wanted to do that—times that the thing I was doing wasn’t working out or left me feeling underconfident and I really wanted to return to doing something I felt I knew how to do. But then I would get a career coach and I would find that helpful.”
Everyone I talked to acknowledged that financial pressure can be a huge factor.
“If you're not employed,” Camille wrote, “this can be harder to figure out. Especially if you have a financial need to find something, it's tempting to take the first thing that seems ok. And if you've had a hard time getting any interviews, it might be correct to settle for the first thing that seems like it will work for you.”
At the end of the day, you need to do what’s best for you. Taking something because you need to shouldn’t stop your process of finding what you want to do. If it turns out that you find that position six months after taking something out of financial need, you shouldn’t be afraid to leave. Sure, your employer will be disappointed that you didn’t stay—but their fault for not providing the kind of opportunity worth staying at. Also, just because you leave after a short period doesn’t mean you still can’t accomplish a few things and help with transition in a way that still makes them glad they had you for that time. Leaving a job doesn’t have to mean burning a bridge.
As to how you find that thing you really want, that’s another post entirely but one person I spoke to had a really great approach:
“I tend to do my searches by identifying my universe of interest/opportunity based on what I want to be learning… then targeting based on that. Then sharing what I'm looking for with community nodes and seeing if they have any suggestions/ideas that may not be on my radar. From there, you should have a pretty good list to work from.”
