Hiring for your startup can feel like a full-time job – especially when you’re trying to fill critical roles. But when do you stop going it alone and bring in outside help? In this guide, we’ll walk through when to hire a headhunter, how they work, and what alternatives exist for startup founders trying to scale their team quickly and effectively.
What Does a Headhunter Actually Do?
A headhunter is a recruiter who proactively sources and attracts top talent – especially candidates who aren’t actively looking for a job. They’re not just posting jobs and hoping someone applies; they’re hunting down high-impact professionals for specific, strategic roles.
Here’s how they’re different from other options:
- Headhunter: Targets passive candidates for specific roles (often senior/critical hires)
- Recruiter: May work in-house or externally; focuses more on active candidates
- Executive Search Firm: Specialized headhunters, typically focused on C-level roles, often retained on long-term contracts
For startups, a good headhunter can open doors to candidates you’d never reach through your network or job ads.
5 Signs It’s Time to Hire a Headhunter
Not sure if you’re ready? Here are five clear signals:
1. You’ve Tried Everything… and Still Can’t Find the Right Candidate
If you’ve posted on every job board, asked everyone in your network, and still can’t find someone who fits, it may be time to bring in a pro.
2. You’re Hiring for a Critical Role
CTO, CFO, Head of Product, VP of Engineering – these roles define the future of your company. Hiring the wrong person (or hiring too slowly) can cost you more than a recruiter ever will.
3. Your Internal Team Is Overwhelmed
Startups move fast. If your internal team is already juggling fundraising, product dev, and customer acquisition, sourcing candidates might be the last thing on their list. A headhunter takes that burden off your plate.
4. You Need Passive Talent
The best candidates usually aren’t applying for jobs. Headhunters are experts at outreach – finding people who are a perfect fit, even if they’re not actively job-hunting.
5. Every Day Without That Hire Costs You
If you’re losing deals, delaying launches, or burning out your team because of a missing hire, the opportunity cost is real. Time-to-hire matters.
This TechCrunch panel breaks down the most common patterns – and shows you’re not alone in hitting these roadblocks. Talent partners at top VC and PE firms see the same hiring issues across hundreds of startups – from unclear job scopes to overextended founders and missed hiring windows.
The same goes for experienced headhunters: most of them have worked with dozens of startups, many facing the exact same hiring pain points. If several of the signs above sound familiar, it’s a good signal that talking to a headhunter could help bring clarity, even if you’re not ready to engage one yet. Sometimes just hearing how others have solved the same problem is enough to change your hiring decisions.
How Much Does a Headhunter Cost?
Headhunters typically charge:
- Contingency fee: Paid only if they place a candidate (often 15–30% of first-year salary)
- Retained search: Paid upfront or in phases (often for executive roles)
Yes, it’s an investment – but consider:
- How much time do you or your team spend on hiring?
- How much is a bad hire costing you?
- How fast do you need to move?
Often, working with a headhunter saves both time and long-term cost, especially when speed and quality are non-negotiable.
When You Might Not Need a Headhunter
Sometimes, other methods work just fine:
- You’re hiring junior roles that get lots of qualified applicants
- You have strong inbound interest (e.g., your startup just got press or funding)
- You have an experienced internal recruiter who can handle the pipeline
In these situations, a founder-led hiring strategy can be both faster and more cost-effective. Y Combinator’s “How to Hire Your First Engineer” post outlines five core ways startups can find candidates without external help: leveraging personal networks, generating inbound interest, cold outreach, attending meetups, and, if needed, working with a recruiter. While it’s framed around engineering hires, the sourcing playbook applies to almost any early-stage role.
You can also watch this interview with Lever’s CEO Sarah Nahm for more insight into how founders can approach hiring as a company-defining task.
But once your company starts to scale, and roles become more specialized or strategic, that DIY approach often breaks down – and that’s when a headhunter can add real value.
Case Snapshot: Scaling Fast After Series A
A Series A startup in the healthtech space came to one of the headhunters we know after trying to fill a CTO role for over 6 months. They had a great product and a series A funding of £3m, but no one in-house could run a serious talent search while also building the team.
They took over the search and placed a top-tier CTO in under 60 days – someone who wasn’t even on the market, but was the perfect fit.
Since then, the team has doubled in size, raised another round, and continues to work with them for executive hires.
Checklist: Is It Time to Hire a Headhunter?
- You’re hiring for a senior or mission-critical role
- You’ve already tried your network and job boards
- You need a hire fast – not six months from now
- Your internal resources are stretched thin
- The opportunity cost of a bad hire is high
If you checked 3 or more, it might be time to talk to a headhunter.
Looking for a headhunter for your startup?
We track and review firms that specialize in tech startups, VC-funded growth, and executive search.
See our list of the top 20 executive search firms, featuring both large headhunting companies (the ‘SHREK’ firms) and smaller, more agile firms ideal for startups.