How to build a C-level hiring system when the founder has never hired executives

Hiring your first executive, such as a CFO or a VP of Engineering, is hard for any founder. You can't vet a candidate in an area you don't know yourself. But this is solved by a system, not by experience.

Step one: describe what the person needs to accomplish. First, put together a scorecard: list the qualities and outcomes you need and rate each candidate on a scale from one to ten. This is what Howard Ting, CEO of Cyberhaven, does. He isn't sure he fully understands what a strong technical leader should look like, so he relies on the opinions of friends, board members and advisors.

Step two: borrow expertise. Where you are not an expert, bring in people who understand the function: investors, independent board members, executives you know. They will help draw up the criteria and run the functional part of the interview. Many funds have talent partners for their portfolio companies, for example Greylock and a16z, and it is worth using them.

Step three: choose how to search. First, search through your network and your investors. If you need a C-level or VP-level executive, Keith Rabois, in a conversation with Elad Gil, advises bringing in specialized executive search firms: they know how to find such candidates, have vetted them before and add discipline to the process, such as weekly meetings. One practitioner advises searching on your own for two weeks first and only then deciding whether you need a search firm.

Step four: assess on real work, not on the résumé. In an a16z discussion on hiring a VP of Product, the advice is to use a structured assessment framework (mission, goals, competencies), give the candidate a work assignment or presentation, and spend enough time together. Gokul Rajaram says interviews are not enough: for such a critical role, you need to spend time with the person.

Step five: always check references. For rank-and-file employees there are sometimes exceptions; for executives there are none. Rabois suggests asking one question: “If this person joined my company, would you go work for them?” Ask specific rather than general questions, and be sure to talk to people outside the list the candidate gave you.

And finally: hire before you become the bottleneck. Elad Gil writes that when the first experienced executive works out, many things start happening on their own: people get hired, deals get closed, processes tighten up.

Sources:

1. Elad Gil — Hiring, managing, and firing executives: interview with Keith Rabois and Hiring executives
2. Vertex Ventures — 3 rules for hiring your first executive team (Howard Ting, Cyberhaven)
3. a16z — How Founders Hire a VP of Product and a podcast summary
4. First Round Review — Assembling an executive leadership team is daunting
5. Notable Capital — Exec Search: How to Get It Right
6. For Entrepreneurs — Extreme referencing
7. Engineered — How to hire your first VP of Engineering