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How to Uplevel Your Startup’s Executive Hiring Process

September 26, 2023

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.

Aligning before you hire

We recommend a three-pronged approach even before you start the hiring process.

  1. Audit your culture: Before sourcing executives, you need to first understand what your leadership stands for and what type of leader will round out your team. By knowing this you can better articulate company culture and find the right addition to round out the team. Ask yourself: 
  • What values do your company have?
  • What qualitative skills can help round out your executive team?
  • Remember: Diversity includes diversity of thought and background—this not only strengthens products but also makes better organizations.
  1. Assess your team—and yourself: As a leader, do you know where you’re spending your time? What should you give up? What functional experts can help fill any gaps? We’re fans of this concept of “giving away your Legos.”   

  2. Know what good looks like: Once you’ve determined any existing capabilities and have identified any gaps, understand what good looks like in this market. Leverage advisors, board members, and investors to help calibrate this standard of excellence.

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.” 

Refining the interview process

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:

  • GGV Managing Partner Glenn Solomon recommends “spending time together in a casual setting. Getting to know someone on a hike or over dinner can really help ensure that both parties are prepared for a close working relationship.” 
  • Consider simulating an on-the-job project or pre-hire exercise so each side knows what to expect before the hire is official, Glenn adds.

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:

  • What's his or her leadership style?
  • How did he or she lead the company?
  • How did he or she build a team?
  • What is he or she known for?

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.

Measuring the first 90 days

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:

  • Staying in touch even after signing: Minimize your chances of things going awry by checking in regularly before the first day. Consider sending handwritten notes or if appropriate, sending “love bombs” of things that you know that person will enjoy.
  • Focus on the onboarding process: Set an executive up for success by proactively scheduling the right meetings, identifying stakeholders, providing reading materials, and more.
  • Creating a culture of feedback: How will this executive know if he or she is executing on the right things? Don’t skip the 30-, 60-, or 90-day check-ins. It’s important that this person can hear feedback directly from the founder or CEO, his or her peers, and the team he or she is leading. 

Stripe’s Claire Hughes Johnson also shares more ways to evaluate an executive’s impact, such as asking: 

  • Is this person attracting any talent in the first three months? (Are people following him or her to your startup?)
  • Is this person adding observations about gaps in talent? (Is this person then recommending people to recruit?)

Resources we love

  • How Diversity Makes Us Smarter”: Learn how diversity can enhance creativity, “improve the bottom line of companies, and lead to unfettered discoveries and breakthrough innovations.” [Scientific American]
  • Our 6 Must Reads for Hiring Tactics That Break the Mold”: Get inspired by examples of best-in-class hiring practices at companies like Medium, Atlassian, Thumbtack, NerdWallet, and more. [The Review by First Round Capital] 
  • When Hiring Execs, Context Matters Most”: This classic piece from 2017 explains how “companies have been hiring and developing these generic workhorse leaders when what they really need is a thoroughbred whose strengths are specifically suited to a particular racetrack.” [Harvard Business Review]

Takeaways & next steps 

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:

  • Aligning on your team’s culture and skills gaps
  • Running a thoughtful search that includes a structured interview process and strong onboarding experience with 30-, 60-, and 90-day check-ins.
  • Being ready to make some hard calls if it’s not a fit

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.