By Sean Cleary, Partner and Cybersecurity Practice Lead
3 Takeaways
- The signal is clear. Head of Security searches among early- and mid-stage companies we work with are on track to double for a second straight year.
- Few candidates do both jobs well. A first security leader has to cover enterprise assurance and hands-on engineering. Decide which two or three skills matter most right now.
- Timing is the payoff. In our 2026 Future of Tech Leadership research, 87% of the most execution-mature organizations bring security in at initial design. Your first security hire is how you get there.
October is Cybersecurity Awareness Month, and I want to use it to talk about a hire that gets too little planning for what it carries: the first Head of Security at a growing company.
Why So Many Startups Are Hiring a Head of Security Now
Our own search activity is one of the clearer market signals I have. Among early- and mid-stage companies in Riviera’s client base, Head of Security searches in 2025 doubled the 2023 and 2024 total combined, and we expect them to double again in 2026. Across our security practice, placements are on pace to grow fourfold this year.
The conversations behind those numbers have shifted. A couple of years ago, a startup hired its first security leader after a big customer forced the issue. Today founders call earlier, usually because three pressures land at once: enterprise buyers sending long security questionnaires, AI features widening the attack surface, and investors asking about security posture in diligence.
The Paradigm: Enterprise Assurance and Hands-On Engineering
Here’s the tension I walk founders through on almost every early-stage search: your first security leader has two jobs that pull in different directions.
The first is enterprise assurance: SOC 2 and ISO 27001, customer security reviews, and sitting across from a Fortune 500 CISO to keep a deal moving. That work runs on trust, documentation, and executive presence.
The second is hands-on technical work: securing cloud infrastructure, reviewing architecture, building detection, and fixing identity sprawl before it becomes an incident. At this stage there’s no team to delegate to. The Head of Security is the team.
People who excel at both exist, and every company in your market is calling them. Most strong candidates lean one way.
Pick Your Top Two or Three Skills
The searches that go well start with one question: what has to be true in 18 months? Then work backward.
- If enterprise revenue depends on passing security reviews, weight assurance, compliance, and customer-facing credibility.
- If you’re shipping AI features into regulated industries, weight product security and AI risk.
- If your infrastructure is growing faster than your controls, weight cloud security engineering.
Pick two or three, then name the tradeoff out loud. A builder still learning the audit side needs a compliance automation platform and perhaps a fractional GRC advisor. An assurance-first leader needs a strong security engineer as hire number two. Both models work. The job description that asks for eleven things at equal weight is the one that stalls.
Why Hands-On Matters More in the AI Era
Our 2026 Future of Tech Leadership Report, based on nearly 1,000 technology leaders, makes a strong case for the hands-on side. Among Advanced organizations, 87% integrate cybersecurity, legal, and governance at the initial design phase. Among Emerging organizations, 14% do. And 42% of technology leaders at Advanced organizations spend more than half their time directly engaged with the build, compared with 18% at Emerging organizations.
At a startup, security enters at design only when your security leader is close enough to the engineering work to be in that room. That’s the strongest case for hands-on capability, and it grows as AI features move into production. I covered the mechanics in What Is Shift-Left Security?
Four Practical Steps
- Write the 18-month mandate before you write the job description.
- Rank the skills, and get your CEO, CTO, and board sponsor to agree on the order.
- Choose the title deliberately. Head of Security signals a builder. CISO signals board-facing scope.
- Plan hire number two now, so it covers your first hire’s weaker side.
Frequently Asked Questions
When should a startup hire its first Head of Security?
Most companies we work with hire a dedicated security leader when enterprise customers start requiring security reviews, when AI products expand the attack surface, or ahead of a raise where investors examine security posture. Hiring ahead of those pressures puts security in the room at design.
What skills should a first Head of Security have?
Prioritize two or three skills tied to your 18-month goals: enterprise assurance and compliance, cloud security engineering, or product and AI security. Define the tradeoffs up front and plan your second security hire to cover the gaps.
Should a startup hire a Head of Security or a CISO?
A Head of Security title typically fits a hands-on leader who will build the function. A CISO title signals executive and board-level scope. Many companies hire a Head of Security first and grow the role into a CISO seat as they scale.
Related: How to Structure a Security Organization by Stage, Risk Profile, and the Bench Beneath the CISO
Sean Cleary leads the cybersecurity executive search practice at Riviera Partners. Connect on LinkedIn.