Hiring can make or break your startup. This is especially true once you’re ready to bring on an executive. Given that an executive search process can take anywhere from three months to more than a year, we wanted to share some hiring best practices for founders and CEOs based on decades of experience at search firms and recruiting at places like Meta and Uber.
We recommend a three-pronged approach even before you start the hiring process.
Pro tip: Don’t assume you need to hire executives right away. If your startup’s infrastructure isn’t ready to absorb an experienced exec from a FAANG, for example, you may want to consider bridging the gap with “someone who can give you a few years of building or an up-and-comer,” says Claire Hughes Johnson, a corporate officer and advisor at Stripe and author of “Scaling People: Tactics for Management and Company Building.”
As we all know, candidates are also interviewing you to see if your startup is a good fit. To create a faster process, we’ve learned that sometimes you have to slow down first. This may involve rallying the CEO and other senior leaders who will participate in the interviewing process.
Create a process, and document it: Create a hiring rubric, and write a compelling job description so you’re all on the same page. If you’re using generative artificial intelligence tools for the rough draft, be sure to leave enough time to layer in your own voice and tone. For early-stage startups looking to attract experienced executives, you may need to pause and clarify your mission, vision, and other messaging.
Engage your interviewers: Invest time in architecting the right interview panel, including board members. We recommend being deliberate about the number of interviews (no more than five rounds is ideal) and who is involved at each stage (for example, we don’t recommend having an executive’s future direct report join the interview committee). Other ways to enhance the interview process for executives:
Cultivate a strong end-to-end experience for candidates: As always, be thoughtful about crafting a strong candidate experience. Don’t underestimate the power of first impressions—avoid excessive rescheduling, and remember to be present during interviews. Candidates can tell when you’re distracted. Not only is a great candidate experience the right thing to do, but word of mouth about positive (and negative) experiences is also likely to travel and may even surface in forums like Glassdoor and Blind.
Be diligent about checking references: Structured reference calls can help you get a more accurate picture of a candidate. Consider following a checklist with behavioral questions like:
Pro tip: Approach back-channel references with care—the venture-backed startup world is small, and many people are connected by one degree of separation. If you do decide to contact someone that your candidate did not list as a reference, it's recommended that you let your candidate know before you initiate that contact. For example, you might say: “I see that we know some people in common. I’ll be reaching out to them just to have a discussion.”
As always, please be mindful of confidentiality concerns as well—for example, reaching out to someone associated with the candidate’s current employer may cause issues if it isn’t known that the candidate is speaking with other potential employers.
It’s also a good idea to keep current on the latest as far as applicable laws and regulations that can differ by jurisdiction (for example, pay transparency laws, what you can (and can’t) ask candidates or references as the interviewer, etc.) by consulting with legal counsel.
So you’ve found—and hired—an executive who can help elevate your startup. Congrats! Given that onboarding starts weeks before a new hire starts, we recommend best practices like:
Stripe’s Claire Hughes Johnson also shares more ways to evaluate an executive’s impact, such as asking:
For founding teams looking to scale, building out an executive team involves a certain level of self-reflection. What are the gaps, and how can you round out your bench? Start by:
If you follow some of these strategies for building a high-performing executive team, we’ve seen firsthand the success stories of finding—and retaining—someone who can help take your startup to the next level.