Paths to VC Operating and How to Break In

“How to break into VC” chats are typically some of the most popular discussions we host for Primary’s Mastermind Networks—professional growth communities for ascendant startup operators. But many of these operators love, well, operating.

So we asked Cassie Young to join us recently to talk about lessons learned going from Chief Revenue Officer at Sailthru and Chief Customer Officer at CM Group to an Operating Partner and now check-writing General Partner at Primary.

Here’s her advice for operators—at all stages of their careers—considering a move to VC operator roles.

Align your experiences to funds with relevant focus areas

As you begin your search, it is essential to consider both the stage of the VC firm and how your background and skill set can align with its focus areas. “You should have had some degree of experience at a company stage that's in near proximity to the firm’s wheelhouse and portfolio,” says Cassie. “So if you've only been at series D-plus startups, it's going to be hard to break into a seed-oriented venture fund.”

Also be thoughtful about where your skills could offer immediate value to the firm’s portfolio—for example, if you have experience with marketplace business models, understand who the best marketplace investors are and approach them about roles. Firms will always appreciate candidates who can quickly establish rapport and credibility with their founders and their management teams.

Understand a fund's portfolio support model

There are two ends of the portfolio support spectrum: fast capital (e.g. Tiger Global) versus value-oriented engagement (e.g. Insight). But even within the value-oriented group, firms employ different types of models. Some firms offer mostly self-service resources to founders, whereas others take a more “white glove” approach; Primary is in the latter camp and works closely in the trenches alongside portfolio companies.

Most firms, however, will fall in a “messy middle.” Many operators at these firms end up as what Cassie calls the “kitchen sink” of the firm; they will be tasked with every possible non-investing job, including events, hiring, PR, programming, and community building. Per Cassie’s suggestion, consider: Are you actually going to have the opportunity to flex your operating muscle, or will you be too busy taking care of everything else that needs to be done?

“It’s actually fine if it is more of a catch-all role,” says Cassie. “You just want to know what you're walking into and make sure that sort of broader, more generalist role makes sense for you, your background and your career goals.”

Find various ways of networking

Networking is the main way of breaking into VC—and given this will be an important component of any VC job, show that you can walk the walk. Some tactics include seeking out alumni from your college who work in the ecosystem, finding affinity points between people, and ending every networking meeting asking a question such as "are there two or three other people in your network, based on what I've shared, that might be helpful for me to meet?”

Another underrated source for networking is tapping into your current company’s board members. “If your board member is coming in to do a fireside chat, ask the company to stand up office hours with the board member. Could you pop in for 15 minutes? If you're in a senior operating role at a company, you should get to know your board members for a host of reasons, especially if you are interested in pursuing a role in their world,” suggests Cassie.

Offer your help and build your brand

VC firms all have founders hungry to connect with operators with relevant industry knowledge; no matter your years of experience, offer your help to VC firms with informal advisory. “Playing the long game with relationship building is hugely important. Be a recognized expert to start building your personal brand,” says Cassie. This might be offering to take advisory conversations with their portfolio companies or even as simple as commenting on the firm’s LinkedIn content.

Get smart and be passionate

Put simply, if you’re going into VC, you need to be articulate on startups. “It's crazy to me when we meet someone and we ask, ‘what's a space you're excited about and two or three startups you've been following in it?’ and they just list the first two companies they see on our website versus being really passionate about a pocket of the tech landscape. We can immediately sense when someone is not authentic or has not done their homework.

It is equally important to understand some of the basics of VC. Recommended reading for anyone breaking into venture are Venture Deals and Mastering the VC Game. Other resources include: VCPlatform.com, John Gannon’s blog, StrictlyVC.com, and Axios Pro Rata.


If you want to grow in your startup role or learn more about a career in VC, we encourage you to join Primary’s Mastermind Networks for community and programming focused on accelerating careers. If you’re looking to join a fast-growing startup to get operating experience, you can fill out this form here, and we’ll connect you with our portco’s talent teams and founders.
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