Why Pairing Junior Executives With External Mentors Can Accelerate Your Hiring and Their Professional Development

Often at a startup it’s better to hire for talent, ambition, and commitment, than years in role or ‘did they have the job already somewhere else.’ For example, imagine a high-performing Operations IC at Stripe, with relevant experience and an itch to get into a role that allows her to spread her wings further. My intuition? Hire. Don’t worry that she hasn’t had a senior title or whatever. Just get her on board.

And then build scaffolding around her. Success isn’t her merely a signature on the offer letter, it’s making sure she excels as part of the team. And one way to help is with mentorship. Not just inside of the company but outside. Ask her if there’s someone senior in her career that’s been a great manager, and if so, bring them on as an equity-compensated advisor to your company. If there’s someone in industry she really admires but doesn’t yet know, reach out to them on her behalf. Or ask your cap table who is the best “XYZ” that they know and give them some skin in the game. Monthly 1:1s and as-needed tactical advice, introductions, and so on.

What should your relationship (as a founder) be with this person? They [mentor and mentee] need to have safe space together— neither can feel like you’re asking the advisor for performance feedback all the time because if so it’s less likely they’ll have honest, open conversations. But it is ok to keep open lines and ask for periodic feedback on how you can best help the team member grow, and/or pass your thoughts to the mentor on growth opportunities. Remember, the idea is that you’re all in this together on behalf of the company, and your employee.

I’ve also found that during a recruiting process telling these types of candidates that they’ll get an ‘advisor equity budget’ to bring people closer to the company who can be useful is a signal of trust and agency. You can even present it as part of their ‘comp’ — an equity grant they have ability to distribute (with your approval).

Sometimes founders will question whether it’s truly a ‘good hire’ if they need to throw extra equity at an outside advisor. My POV is:

a) You’re hiring the type of person with very high ceiling before the rest of the market potentially realizes it. This is like getting a great athlete on their rookie contract. Their success will not just pay direct dividends but they are likely to be talent attractors going forward.

b) By bringing on someone a more junior into the role, you are probably giving them an initial equity grant a bit below what it would take to recruit a ‘been there, done that’ exec. Think of the advisor grant as coming out of that delta. You’re still ‘saving’ equity from the pool.

c) The advisor might have benefit to your startup beyond just directly helping the team member. They become another recruiting/networking vector for you to tap judiciously.

So that’s my argument for this type of hire and the secret way I share with founders to make it work. Good luck!

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