TL;DR
Scaling your startup? Timing the hire of a Head of People is critical. Too early, and you risk wasting money or under-using their expertise. Too late, and you’re drowning in “people debt”—ineffective ways of working as you scale, retention problems, and operational issues that slow you down.
In this post, we’ll break down five signs that scream it’s time to make this strategic hire, so you can scale with confidence.
Why Founders Need to Rethink the Head of People Role
10 years ago, HR was all about compliance—managing payroll, keeping the workplace legally sound, and tracking holiday requests. Compliance still matters, but it’s a tiny part of what a Head of People can do for your business.
A great hire here will be an agent of change and continuous improvement: your culture architect, people strategist, and partner in building scalable systems that keep your team thriving as you grow.
Bringing on a Head of People isn’t just about fixing what’s broken—it’s about being proactive, aligning your people strategy with your business goals, and setting the stage for sustainable, profitable growth.
What a Head of People Brings to the Table
In a startup, a Head of People rolls up their sleeves to support you with:
- Designing and managing culture, beyond values on your careers page: Ensuring how your teams work reflects and supports your business goals today and tomorrow.
- Retaining Top Talent: Creating clear career paths and meaningful opportunities for growth.
- Streamlining Operations: Designing systems for hiring, onboarding, and team engagement that scale with your company.
Think of them as the glue that holds your team together while you focus on product, sales, and growth.
5 Signs You’re Ready to Hire a Head of People
1. Your Headcount Is About to Boom
Secured Series A funding? Doubling (or tripling) your team in the next year? High growth is exciting, but it comes with a hefty price tag in terms of operational complexity and culture strain.
🚩 Red Flags:
- You’re hiring at breakneck speed but lack a streamlined hiring and onboarding process.
- Expanding into remote or multiple office locations has led to fragmented communication.
🧩 The Fix:
- A Head of People can design scalable systems for onboarding, communication, and career development to ensure your team grows intentionally—not chaotically.
2. Your Ways of Working Feel… Off
What started as a close-knit, mission-driven team now feels disjointed. Maybe it’s increasing turnover, lukewarm engagement, or turf wars between departments.
🚩 Red Flags:
- Rising turnover or feedback indicating disengagement.
- Cross-functional collaboration feels strained or unclear.
- Teams are struggling to embody your company values.
🧩 The Fix:
- A Head of People can diagnose employee experience, reset your cultural foundations, and create systems to foster alignment and collaboration.
3. Retention Is Slipping, and Career Development Feels Nonexistent
Your top performers are starting to leave—or they’re asking questions about what’s next, and you don’t have answers. Talent is your biggest lever for success, and without clear career pathways, you risk losing it.
🚩 Red Flags:
- People manager capability needs to come up, fast
- High-potential employees asking for clarity on growth opportunities.
- Leaders struggling to promote from within for key roles.
- An uptick in requests for training and development that you can’t deliver on.
🧩 The Fix:
- A Head of People can create structured career pathways, launch training programs, and ensure your team knows you’re invested in their growth.
4. Your People Operations Are Buckling Under Pressure
Managing hiring, onboarding, payroll and compliance as Founders worked fine when you were small, but now you’re grappling with workforce planning, DEI initiatives, and performance reviews. It’s too much for you to handle and is no longer a cost effective use of your time.
🚩 Red Flags:
- Founders spending a disproportionate amount of time on People Operations
- Remote teams or satellite offices are struggling with alignment.
- Diversity and inclusion gaps are becoming more visible—but not addressed.
- Administrative processes (e.g., hiring, onboarding, performance reviews) feel clunky and time-consuming.
🧩 The Fix:
- A Head of People can centralise and streamline the end to end employee experience and supporting processes, balancing compliance with the strategic elements of building a thriving team.
5. You’re Thinking About the Long Game
You’re no longer just trying to survive; you’re building for scale. This means your team needs a clear vision of how they’ll grow with you—and you need the systems to support them.
🚩 Red Flags:
- Communication breakdowns between teams are slowing you down.
- Onboarding feels inconsistent, leaving new hires frustrated.
- You’re feeling the pressure to improve retention as a key metric.
🧩 The Fix:
- A Head of People lays the groundwork for scaling successfully—codifying culture, improving retention, and ensuring your team is aligned with your long-term goals.
Avoid These Common Mistakes When Hiring a Head of People
⚡️Waiting Too Long: Don’t wait until morale has tanked or retention is spiralling out of control. By the time you notice, the damage may already be done.
⚡️ Focusing Only on Compliance: A Head of People isn’t just a rulebook enforcer—they’re a strategic leader who helps you build for the future.
⚡️ Skipping Role Clarity: Be crystal clear about what you need from this role now and how it will evolve as you scale.
The Bottom Line
If your startup is scaling fast, you can’t afford to treat the Head of People role as an afterthought. The right hire at the right time can transform your business—helping you avoid costly people problems while empowering your team to thrive.
Look for these signs:
🔔 Your headcount is growing exponentially.
🔔 Culture, morale, and retention feel shaky.
🔔 You need scalable people systems and clear career pathways.
Bringing on a Head of People isn’t about offloading admin tasks—it’s about aligning your people strategy with your vision, enabling long-term success.
