Hiring Your First 10
Your first 10 hires will define your company culture, set the pace of execution, and largely determine whether you succeed or fail. This guide covers everything from deciding when to hire to building a team that can take you from 0 to 1.
What's Inside This Guide
When to Make Your First Hire
Hiring too early burns runway and dilutes focus. Hiring too late causes burnout and missed opportunities. Here's how to know when you're ready.
Signs You're Ready to Hire
Signs You're NOT Ready
Which Roles to Hire First
The order of your first hires depends on your business model, founder skills, and current bottlenecks. Here's a framework for prioritization.
| Business Type | Hire #1 | Hire #2 | Hire #3 |
|---|---|---|---|
| B2B SaaS | Full-stack Engineer | Customer Success | SDR/BDR |
| Consumer App | Mobile Engineer | Designer | Growth Marketer |
| Marketplace | Ops/Supply Manager | Full-stack Engineer | Community Manager |
| Dev Tools | Senior Engineer | Dev Advocate | Technical Writer |
| E-commerce/D2C | Performance Marketer | Ops/Fulfillment | Customer Support |
Role Prioritization Framework
Score each potential role on these dimensions (1-5):
Hire the role with the highest total score first.
Co-founder vs. Employee
One of the most important early decisions: should your first hire be a co-founder or an employee? The wrong choice can be devastating.
→ Hire a Co-founder If...
→ Hire an Employee If...
The "VP of Engineering" Trap
Many founders try to hire a "VP of Engineering" as employee #1 when they really need a technical co-founder. VPs expect teams to manage, infrastructure to optimize, and processes to implement. At employee #1-5, you need builders who write code, not managers who delegate. If you need senior technical leadership and can't offer co-founder equity, consider a fractional/advisory CTO until you can hire a full engineering team.
Writing Startup Job Descriptions
Startup job descriptions should filter for people who thrive in ambiguity, not just check skills boxes. Here's what to include.
Job Description Template
What's the mission? Why does this company matter? Why now?
What will they build? What impact will they have? Why is this role exciting?
Concrete deliverables for the first 6-12 months. Be specific, not generic.
Skills and experience that actually matter. Separate "required" from "nice to have".
Culture fit signals. "You should NOT apply if..." is powerful.
Compensation range, equity, benefits, growth opportunity, team.
What Works
What Doesn't
Sourcing Candidates
At the early stage, 80% of your hires should come from your network. Job boards alone won't cut it. Here's the sourcing hierarchy.
| Channel | Quality | Volume | Cost | Best For |
|---|---|---|---|---|
| Personal network | Highest | Low | Free | Hire #1-3 |
| Team referrals | Very High | Medium | $2-5K bonus | Hire #4-10 |
| Investor intros | High | Low | Free | Senior hires |
| LinkedIn outbound | Medium | High | $100-500/mo | Engineering, Sales |
| AngelList/Wellfound | Medium | High | Free-$500/mo | Startup-minded |
| Twitter/X | Variable | Medium | Free | Dev tools, Creator |
| Recruiters | Variable | High | 20-25% salary | Urgent senior roles |
Outreach Message Template
Subject: [Specific thing you noticed] + early role at [Company]
---
Hi [Name],
I came across your [specific work/project/post] on [where you found it]. [One sentence about why it impressed you.]
I'm building [Company] — [one line pitch]. We're looking for our first [role] to [specific impact they'd have].
Would you be open to a quick call? Even if timing isn't right, I'd love to get your perspective on [specific question about their expertise].
[Your name]
The Referral Multiplier
After every meeting or interview (even rejections), ask: "Who else should I be talking to?" This single question can 3x your pipeline. Offer a meaningful referral bonus ($2-5K) for successful hires—it's still cheaper than recruiters.
Interview Process Design
Your interview process should evaluate skills, culture fit, and startup readiness while respecting candidate time. Here's a proven structure.
| Stage | Duration | Focus | Who |
|---|---|---|---|
| 1. Recruiter Screen | 15-20 min | Basics, logistics, interest | Founder or hiring mgr |
| 2. Hiring Manager | 45-60 min | Experience deep dive, role fit | Founder |
| 3. Technical/Skills | 60-90 min | Can they do the job? | Technical evaluator |
| 4. Take-home/Work Sample | 2-4 hrs | Real work quality | Async |
| 5. Culture/Team Fit | 30-45 min | Values, working style | 2-3 team members |
| 6. Founder/CEO Final | 30-45 min | Sell, Q&A, concerns | CEO/Founder |
| 7. References | 3x 20 min | Verify and discover | Founder |
Essential Interview Questions
- • "Walk me through a project you're most proud of. What was your specific role?"
- • "Tell me about a time you failed. What did you learn?"
- • "What's the hardest technical/professional problem you've solved?"
- • "Why a startup? Why this stage? Why now in your career?"
- • "Tell me about a time you had to figure something out with no guidance."
- • "How do you handle ambiguity when priorities shift?"
- • "What do you want to learn in your next role?"
- • "What kind of manager brings out your best work?"
- • "What's something you believe about [their field] that most people don't?"
The Work Sample Test
The best predictor of job performance is a work sample. Pay candidates for their time ($200-500) and give them a real problem your company faces. For engineers: debug real code or build a small feature. For marketers: create a campaign brief. For sales: do a mock discovery call. You'll learn more in 3 hours of real work than 10 hours of interviews.
Reference Checks That Work
Most reference checks are useless because people only provide references who will say nice things. Here's how to get real signal.
Reference Call Structure
Questions That Get Real Answers
Backdoor References
The most valuable references are people the candidate didn't provide. Use LinkedIn to find mutual connections who worked with them. Ask: "I'm considering [Name] for [role]. Off the record, what should I know?" You'll get candid feedback you'd never hear otherwise. Always do this for senior hires.
Compensation & Equity
Early-stage compensation is about balancing cash constraints with competitive offers. Equity is your advantage—use it strategically.
| Employee # | Typical Equity | Cash (% of Market) | Notes |
|---|---|---|---|
| #1 | 1-2% | 50-70% | High risk, high reward |
| #2-3 | 0.5-1% | 60-80% | Key early believers |
| #4-5 | 0.25-0.5% | 70-85% | Post-seed typical |
| #6-10 | 0.1-0.25% | 80-90% | Series A range |
| #11-20 | 0.05-0.1% | 85-95% | Closer to market |
Equity Grant Components
Explaining Equity Value
Most candidates don't understand equity. Create a simple model: "If we hit our Series A targets and you own 0.5%, your equity could be worth $X-Y based on typical valuations." Be honest about dilution and risk. Candidates who understand and still choose your startup are the ones you want.
Making & Closing Offers
The offer stage is where deals die. Move fast, be transparent, and remember: you're still selling the opportunity.
The Offer Process
Offer Letter Must-Haves
Closing Tactics
Handling Competing Offers
When candidates have other offers, don't panic. Ask: "What would make our offer the clear choice?" Often it's not about money—it's about role scope, learning opportunity, or team. If you can't match on cash, get creative: sign-on bonus, accelerated vesting, title bump, or additional equity. Know your walk-away point and don't overpay—desperation hires rarely work out.
Onboarding for Startups
Great onboarding accelerates time-to-productivity and reduces early turnover. Even at 5 people, you need a system.
30-60-90 Day Plan
Day 1 Checklist
Building Early Culture
Culture isn't ping pong tables—it's how decisions get made when no one is watching. Your first 10 hires will cement patterns that last for years.
Culture Definition Framework
Answer these questions to define your culture intentionally:
High-Performance Culture Traits
Toxic Patterns to Avoid
The Culture You Get is the Culture You Tolerate
Your first toxic hire, if not addressed, signals that behavior is acceptable. Your first brilliant jerk who ships fast but damages the team sets a precedent. Act fast on culture violations—the cost of a bad cultural hire is 10x worse than a skill gap. When in doubt, fire fast and communicate why.
Common Hiring Mistakes
These mistakes are so common they're almost clichés—but founders keep making them. Learn from others' pain.
01Hiring for credentials over capability
Big company experience often doesn't translate to startup success. Look for builders who've done more with less, not people who managed large teams.
02Moving too slow
Great candidates get multiple offers. A 4-week process loses the best people to companies that move in 2 weeks.
03Hiring generalists when you need specialists (or vice versa)
Employee #1-3 should be versatile builders. Employee #8-10 might need deep expertise in a specific area.
04Over-indexing on technical skills
Skills can be learned; attitude, work ethic, and cultural fit cannot. A mediocre engineer with great judgment beats a great engineer with bad judgment.
05Skipping reference checks
Interviews test presentation skills. References reveal actual performance. The 60 minutes spent on references can save you $250K+ in bad hire costs.
06Hiring to delegate, not to elevate
Your first hires should make you better, not just take work off your plate. They should challenge your thinking and bring perspectives you lack.
07Underestimating culture impact
One toxic hire can destroy a team of five. One brilliant jerk can make your best people quit. Culture debt compounds faster than technical debt.
08Not selling the opportunity
Great candidates have options. If you're not actively selling why your company is special, you'll lose to competitors who are.
Your Hiring Checklist
Use this checklist to ensure you're ready to make your next hire the right way.