Recruiting a senior executive is always a high-stakes decision, no matter the market cycle. But if you’re a tech startup executive navigating a leadership search right now, finding the right candidate (and winning them over) is of particular importance. You need a leader with the right experience to take your company to the next level in an uncertain market, an appetite for the challenges of the role and a willingness to keep learning to stretch their existing skills.
Ready to make that next big hire? Here’s what we advise our portfolio companies to do (and not to do) in startup executive recruiting:
- DO understand the what and why of the role before focusing on who should fill it.
Running a startup is fluid and requires quick decision-making. But once you decide to make a change with an existing role or create a new one, it’s important to take time and care in creating structure around the role. As a practical exercise, be sure that you and your team can clearly articulate why you are making a change and what the new role will require. If hiring for an existing role, pinpoint issues with the previous situation to build out a new spec.
In terms of compensation and equity, seek out market data to see what other organizations can offer your ideal candidates. Call your peers to learn what they’re paying for similar roles. And if you’re looking to uplevel from the current person in the seat, expect compensation, title and equity to increase in turn. Despite the macroeconomic environment, the best executives are still commanding top dollar and have multiple opportunities in front of them. Offer within market range or you will lose out on the best talent.
- DO make your hiring process a top priority.
Timing is everything. The worst thing you can do is “test the waters,” putting feelers out to speak with candidates too early only to pause the search. Or worse, tell them you need to make another hire before you fill the role for which they’ve applied. Be deliberate and execute with conviction.
Follow up with talent candidates with urgency, pouncing and engaging as soon as possible. When actively recruiting — particularly for executives — the best hiring teams adjust their schedules to accommodate the candidate. It’s okay to prioritize candidates: ones sourced by your recruiter or referred in may be higher priority than ones who apply online, but running your process with urgency is best practice.
This all may seem like common sense, but we often hear about hiring teams taking weeks to get a candidate interview scheduled. It’s a competitive environment – don’t stand in your own way!
- DO establish a clear interview process.
First impressions are critical, especially with an increasingly savvy and discerning executive candidate pool. Also, as a startup, you and your team are already busy and want to be smart with your time. Therefore, it’s essential to lay out a clear and organized interview process as you move candidates through the funnel.
Start by creating an interview scorecard so you know who you’re assessing for: think in terms of objective skills and traits as opposed to just “feeling.” Determine who will be part of the interview loop and who can veto the hire versus who is there to assess and sell. If you have direct reports as part of the interview process, clearly communicate to them that their feedback and input is valued and will be taken into consideration.
After the recruiter has done the first screening interview, the hiring manager should take the next meeting, followed by the subsequent interviewers. You don’t want everyone to ask the same questions: determine themes or areas for each interviewer to explore with the candidate (past performance, current skill set, culture fit, situational questions, etc.) and assign to different interviewers in the process. The final meeting with a candidate should be in-person, ideally over dinner, to help with the close.
- DON’T lose sight of your organization’s design.
Be sure you’ve designed the role correctly. If you’re a company with $100M in ARR and looking for a CRO, but you’re telling candidates they will run only new business sales (not expansion), it’s likely you’re going to limit who will be interested. A great (and very honest) candidate might respond this way: “This role is titled chief revenue officer. New business is one part of the revenue team, but so is expansion, and so are renewals. That’s what I’ve done in the past and that’s my skill set. For my next role, I’m looking at moving forward, not backward.”
This concept applies across all functions – be sure you scope the role correctly for a company of your size/stage. Build the organizational structure that maximizes company scaling, not around personalities.
- DON’T go dark during the interview process.
When engaging with executives, every touch point makes an impression. Regularly communicate with candidates during the interview process, clearly plan out who they are meeting and keep the process moving. Even if you’re cooling on a candidate or want to keep them in play while meeting others, keep the executive informed as to where they are in the process.
This also applies to candidates with whom you decide not to move forward. It is always best practice to let people know when you are going in a different direction and provide some feedback on why. This will leave executives with productive input and a positive impression of how they were respectfully treated. You don’t want your company to be thought of negatively in the market.
- DON’T forget to be real with the candidate (and with yourself).
We’ve heard candidates tell us: “The CEO says she only hires A talent, but the whole team around her are B players.” That may well be true, and it takes self-awareness to admit. If you have an earlier-stage team and are looking at upleveling that team, be candid about that. Communicating your plan—that you’re looking to make your first professional or “anchor” hire on the team—sends the signal that you recognize a transition is in order.
Bottom line: Be mindful that candidates are evaluating you and your company. They’ll research the reputation of the company, your other executives, and you. That reputation will impact your ability to hire A players so always be thoughtful of the type of leader and culture you’re creating.
- DON’T skip reference checks.
As executives progress in the interview process, take the time to conduct thorough reference checks. Remember that context is critical for each reference. How closely did this person work with the candidate? What was the nature of their working relationship? If the reference provides mixed or negative feedback, it’s best to validate this before simply writing a candidate off. You should seek additional points of view to determine if there is a pattern of behavior as opposed to just a one-off impression or incident from a single source.
When speaking to references, you want more than a simple “I’d hire them.” Get a holistic view on the candidate by speaking with former managers, peers and direct reports. Speaking with a candidate’s former manager is a necessity; if an executive can’t provide a former manager as a reference, that’s a big red flag. Learn their areas of strength in a past role, where they needed to grow/develop, skills they should hone and anything they’re simply not good at.
- DO break up, swiftly and cleanly, if it’s what needs to happen.
If you decide a candidate is not moving forward, a phone call is the method to break the news. Make sure you do the call yourself; don’t outsource it to a team member or your external search firm.
The tech community is well-connected. You may work with the candidate in the future, and that candidate will probably talk about their interview experience with others. Communicate professionally and in a timely manner regarding why you are not moving forward.
- DON’T lose momentum after the candidate has signed.
Even after your candidate has signed, you’ll want to stay connected and engaged. We’ve heard of candidates turning down other offers just to be wooed back to their current employer. The search for your executive isn’t over until they show up for their first day of work.
After you sign the paperwork, show your new executive love. Send them some company swag. Encourage the team members who were part of the interview process to send congratulatory notes. Ask your board members to do the same. Once you announce the hire internally, let the new hire know they’re welcome to meet people as they prepare to start. If local to their team, consider setting up a lunch or dinner to build rapport.
In conclusion…
Recruiting an executive means recognizing that everything in the interview process is information. You are showing this executive that you know what a considerate, thoughtful, efficient process looks like. As a hiring manager, you are putting your culture, your team dynamics and your awareness of the company’s mission and stage under a spotlight; it should make good sense to an outsider. Remember that the candidate is also evaluating you, and that a lack of consideration, even if unintentional, can tarnish your brand.
When done right, recruiting a top executive can yield you more than a great hire. It can help you better articulate your company’s vision, recognize the stage you’re in and where you need to go next, while finding the right leader to help you get there. Good luck!
The information contained herein is based solely on the opinion of Jenny Kang and Bill Binch and nothing should be construed as investment advice. This material is provided for informational purposes, and it is not, and may not be relied on in any manner as, legal, tax or investment advice or as an offer to sell or a solicitation of an offer to buy an interest in any fund or investment vehicle managed by Battery Ventures or any other Battery entity.
The information and data are as of the publication date unless otherwise noted. Content obtained from third-party sources, although believed to be reliable, has not been independently verified as to its accuracy or completeness and cannot be guaranteed. Battery Ventures has no obligation to update, modify or amend the content of this post nor notify its readers in the event that any information, opinion, projection, forecast or estimate included, changes or subsequently becomes inaccurate.
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