Your First People Ops Hire: When, Who, and Why It Matters More Than You Think

At 15 employees, your startup does not have a People Operations problem. You have a collection of people problems that nobody owns. The co-founder who handles onboarding forgets half the steps. Benefits enrollment happens over Slack DMs. Performance conversations do not happen at all. And the engineer who has been quietly unhappy for three months just gave their two-week notice, surprising everyone except the person who sat next to them.

By 25 employees, these problems have compounded into something much harder to fix. Cultural norms are calcified. Processes that worked at 10 people are visibly breaking. Your best people are frustrated by the lack of structure, and your struggling people are hiding in the chaos.

This is the story at almost every startup that waits too long to hire for People Operations. The role feels like overhead until you need it, and by then you are playing catch-up.

When to Hire

The right time to hire your first People Ops person is when you have 20-30 employees. At this size, the administrative load of payroll, benefits, compliance, onboarding, and offboarding has exceeded what a founder can reasonably manage as a side responsibility. And the cultural load of ensuring new hires integrate well, performance is addressed, and the team feels supported requires dedicated attention.

Some startups hire earlier, around 15 employees, if they are growing fast and expect to double within a year. The logic is sound: it is easier to build the right systems from the start than to retrofit them later.

Waiting until 40 or more employees is almost always too late. By then, you have accumulated cultural debt, process debt, and compliance debt that will take your new hire months to untangle.

What to Look For

The Startup People Ops Archetype

Your first People Ops hire is not an HR manager from a Fortune 500 company. Enterprise HR is primarily about policy enforcement, compliance, and process management at scale. Startup People Ops is about building from zero, wearing ten hats, and creating the employee experience that makes people want to stay.

Look for someone who has worked at a company with 30-200 employees and built programs from scratch. They should have experience across the full spectrum: recruiting operations, onboarding, benefits administration, performance management, compensation, and employment law basics.

The ideal candidate is half systems builder and half empathetic human. They need to set up your HRIS, build your onboarding checklist, and design your compensation bands. But they also need to be someone that employees trust enough to share honest feedback with.

Key Skills

Process design. They will build every people process your company has. Onboarding flows, performance review cycles, promotion frameworks, offboarding procedures. They need to be able to design lightweight systems that work at your current size and can scale.

Employment law literacy. They do not need to be a lawyer, but they need to know enough about employment law to keep you out of trouble. Wage and hour compliance, anti-discrimination requirements, leave policies, and termination procedures vary by state and country, and the penalties for getting them wrong are severe.

Data comfort. Modern People Ops is increasingly data-driven. They should be comfortable with compensation benchmarking, engagement surveys, turnover analysis, and basic reporting. They do not need to be a data scientist, but they should be able to pull insights from your HRIS and present them to leadership.

Emotional intelligence. They will be the person employees come to with sensitive issues. Conflicts with managers, concerns about compensation, personal situations that affect work. They need the judgment to handle these conversations with empathy, discretion, and fairness.

What They Should Do First

Month 1: Foundation

Audit everything. What systems exist. What is documented. What is not. Where are the compliance gaps. What do employees complain about most. Do not change anything yet. Just understand the landscape.

Month 2: Quick Wins

Fix the top three things that are causing the most pain. Usually this is onboarding, benefits confusion, and lack of a clear feedback mechanism. Set up a proper HRIS if one does not exist. Document the processes that are currently tribal knowledge.

Month 3: Infrastructure

Build the compensation framework, the performance review process, and the promotion criteria. These are the three things that most directly affect retention, and most startups do not have any of them formalized until they are past 50 employees.

The ROI of Hiring Early

Every unwanted departure costs your startup 50-200 percent of the departing employee's annual salary when you account for lost productivity, knowledge drain, recruiting costs, and ramp time for the replacement. If your first People Ops hire prevents even two unwanted departures in their first year, they have already paid for themselves.

But the real ROI is harder to quantify. It is the engineer who stays an extra year because they feel supported. The manager who becomes effective because someone coached them. The culture that stays cohesive through rapid growth because someone is intentionally tending to it.

The Bottom Line

People Operations is not overhead. It is infrastructure. Just like you would not build a product without an engineering team, you should not build a company without someone dedicated to the people who build it. Hire earlier than feels necessary, find someone who combines systems thinking with genuine care for humans, and give them the authority to do the job well.