3 rules for startup founders hiring their first executive team, according to the CEO of Cyberhaven
Hiring an executive team is, arguably, the most important thing that a startup CEO will ever be asked to do. With only 24 hours in the day, even the most dynamic leaders will need a team of seasoned professionals on whom they can rely to build sales and product momentum without needing moment-to-moment oversight.
At a roundtable discussion at Vertex Intersect ’24 — the annual gathering of CEOs, founders, and investors hosted by Vertex Ventures US — Cyberhaven CEO Howard Ting gave founders his best advice for hiring and managing their first executives, drawn from his decades of experience at startups like Redis and larger firms including Zscaler, Nutanix, Cisco, and Microsoft.
To kick off the session, Howard gave his top three tips for startup founders as they begin to hire a senior leadership team:
- Know what great looks like: Howard himself served as chief marketing officer at Nutanix, Zscaler, and Redis before joining Cyberhaven as its chief executive in 2020. That means he has a pretty good sense of what to look for in hiring a marketing executive. On the flip side, he has a less intuitive sense of what makes for a truly great engineering leader — so he relies on friends, board members, and advisors to help him get a sense of the ideal attributes for a candidate. Either way, he says it’s beyond important to have that sense of precisely what you’re looking for before you start even interviewing candidates.
- Always be recruiting: Things move fast at a startup, and the team you have today might not be the team you need to meet the challenges of tomorrow. Howard urges CEOs to think ahead a year or two and think about what kind of sales, product, or engineering leader they might need at the next stage of their growth. Then, he says, you can go out and start meeting people who fit that profile, building a relationship ahead of a formal recruitment process.
- Maintain your hiring discipline: No matter how much of a rush you might be in, it’s always better to take the time to undergo a rigorous hiring process. Howard says that those few times he’s rushed an executive hire, he’s regretted it. Ultimately, he says that it’s better for founders to fill the empty role themselves for however many months it takes to properly interview and vet candidates than it is to bring on the wrong person.
As for the hiring process itself, Howard identified two key facets of his vetting strategy. First, he makes a kind of scorecard where he lists out all of the attributes he’s looking for in a candidate, and ranks prospects on a scale of one to ten in each. Those criteria include everything from leadership qualities and domain knowledge to strength of their network and upward career trajectory. The idea, he says, is to help recenter his own thought processes on the needs of the company, rather than letting him get swept away with a charismatic candidate who may rank lower on industry-specific experience, communication style, or other criteria.
Second, Howard says that leaders need to embrace the power of backchannel references. The formal reference process tends to accentuate the positive attributes of the candidate. By taking the time to talk more informally with people who worked with the person, you can create a safe space to hear less flattering feedback.
The goal, Howard says, isn’t to be gossipy — it’s to get a sense of what working with the person is like on their worst day, as well as their best. In an imperfect world, it’s foolish to expect perfection from any candidate. But you still want to know ahead of time what you’re signing up for when there are inevitably bumps in the road. It’s also important to vet the backchannel references, too: You might get a skewed perspective if you’re talking to someone who has any kind of ax to grind with the candidate.
Other highlights from the discussion included the importance of setting goals and expectations for new executives, including who to meet with in their first weeks on the job, and using written feedback to keep them accountable. Howard also shared his strategies for running better board meetings, most of which hinge on beginning preparation as much as four weeks beforehand. He sits down with every executive and employee who’s slated to speak at the meeting and essentially product-manages them through the preparation of their slides, to make sure that the company is giving the board a comprehensive, cohesive, and honest view of the business.
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