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How 23 rising star enterprise VCs got their start in venture — and what other rookie professionals can do to break into the notoriously exclusive industry

Sanjiv Kalevar
  • Business Insider recently identified 23 junior venture capitalists as rising stars in the enterprise investing community. 
  • We asked the nominees what they would share with other young professionals hoping to break into the notoriously exclusive industry.
  • While many advised expanding a professional network as early as possible, others recommended spending time in the trenches of a high-growth startup to learn how to best help founders after moving to the venture side.
  • Enterprise investing, in particular, requires technical chops to find and source the right solutions, many VCs said.
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Some say venture investing is essentially a sales job. But instead of hawking a product or service, investors have to sell themselves.
In Silicon Valley's more recent history, founders have had their pick of VC shops and the partners running them, because funding was easy to get and capital was cheap. Major VC firms battled it out with boutique shops to land hot deals, promising founders the moon and a billion-dollar valuation to make it happen. It's the high-stakes, upscale version of the software salesperson who just wants to get the deal done.
But unlike software sales, venture is a notoriously exclusive industry to break into. The predominantly white, male industry has traditionally recruited from a handful of top-tier business schools and well-known tech companies. Some have been around for decades, and have a well-honed recruiting machine.
"Traditionally, VCs have hired out of business school or former founders," Base10 principal Rexhi Dollaku told Business Insider. "This is changing in a positive way — there are funds that hire out of undergrad, some funds have scout programs where you can learn the craft, and there are increasingly larger angel networks where you can get exposure to early stage investing that fits your financial capability."
As the market shifts and the historic bull run comes to an end, junior level roles at major VC firms could become even harder to get. But as Dollaku explained, there are more entry points into the venture industry than ever. Prospective candidates just have to sell themselves, and their skills, to cost-conscious partners.
That is especially true in enterprise investing, several investors told Business Insider, because there is a technical element to the startup companies and junior VCs have to evaluate their proposed solutions.
"[You have to] create a 'moat' in enterprise investing," Sapphire Ventures senior associate Casber Wang said. "This could be having deep domain expertise and opinions around the space, a robust enterprise VC network, a substantial enterprise industry network, or something else that's uniquely differentiating. Some level of domain understanding is probably the most accessible starting point as a candidate can leverage the internet, publications, and research as a great equalizer."
Enterprise tech has become a catch-all term for any company that sells software to other companies. The range varies widely, from productivity tools like Slack to highly technical services like supply chain logistics and cybersecurity. Because the scope is so broad, Battery Ventures principal Sanjiv Kalevar first chose the field he wanted to focus on, and then worked backward to land at the right VC firm by tapping his growing network of industry insiders.
"Everyone has their own journey into venture investing," Kalevar said. "Some people luck into it, but I took a very methodical approach, very much like a sales rep conducting an outbound campaign. I had a target list of firms, a select group of contacts, and customized outreach messaging for each. If you enjoy the process of getting a job in VC, I think you'll enjoy the actual job of being a VC a lot."
Another way in, according to Wang and other investors, is to spend a good amount of time building or working at a high-growth startup from the ground up. That can help broaden the network of highly technical peers, but will also demonstrate an ability and willingness to get down in the trenches even after someone has moved to the cushier world of venture capital. It's a nearly unanimous sentiment among junior VCs that larger networks result in more opportunities down the road.
"Many of us found our jobs because someone we knew opened a door for us and oftentimes it's not a close connection," Scale principal Susan Liu said. "Same goes for deal flow. Many of my friends and acquaintances have introduced me to interesting companies."
Building a network is a daunting task, especially for new graduates staring down the barrel of a recession and canceled internships that could have opened doors to the exclusive VC world. That's where the sales-esque hustle can come into play, investors said.
"Having moved from Israel to the US to pursue my MBA at the University of Chicago in 2016, I did not have US-based undergrad- and career-related networks to tap into," GGV vice president Oren Yunger said. "To anyone else in the position I was a few years ago, I would recommend being methodical and thoughtful about what you do, and to find creative ways to provide value. Learn from failure and don't be afraid to pivot with your 'go-to-market' motion if something is not working."
SEE ALSO: Pay for top engineers is immune from cuts at startups that fear losing them and would rather slash executive salaries to reduce costs
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