Your first 5 hires will make or break your startup
The first people you hire set the culture, the standards, and the trajectory. Most founders get at least 2 of the 5 wrong. Here's how to get them right.
Why the first 5 matter disproportionately
When you're hiring employee number 50, a bad hire is a problem. When you're hiring employee number 3, a bad hire is a crisis. Every person you add to a 5-person team changes 20% of your culture, your capabilities, and your daily reality.
Your first 5 hires aren't just filling roles. They're setting the standard for everyone who comes after them. They decide what "good" looks like at your company. They establish how decisions get made, how conflicts get resolved, and how hard people work. Every hire after them will be compared to them.
Get these right and you build a foundation that attracts more great people. Get them wrong and you spend the next 2 years trying to fix what went wrong at the start.
The mistakes founders make
Hiring friends
Your co-founder's college roommate is available and "really smart." Your friend from your last job wants to join. They're excited about the idea. They'll work for less. It feels safe.
Sometimes friends are the right hire. But usually they get the job because they're friends, not because they're the best person. And when a friend underperforms, you can't manage them the way you'd manage a stranger. You avoid the hard conversation. You lower the bar. The rest of the team sees this and your standards drop.
Hire friends if they'd be your top candidate even if you didn't know them. Not because they're convenient.
Hiring for right now instead of next year
You need someone who can do the work today. But in 12 months, the work will be completely different. A startup that's 5 people and a startup that's 20 people need different capabilities.
Your first marketing hire shouldn't just be someone who can run Facebook ads. They should be someone who can eventually build and lead a marketing team. Your first engineer shouldn't just ship features - they should be able to set technical standards and mentor junior engineers when you hire them in 6 months.
Hire people who can grow with the company. That usually means hiring slightly more senior than you think you need right now.
Hiring specialists too early
Your company has 4 people. You don't need a "Head of SEO." You need someone who can do marketing broadly - content, ads, email, analytics - because the job will require all of those things and more. Specialists are valuable when you have enough volume to keep them busy. At 5 people, everyone needs to do everything.
Look for people who are good at their core skill but willing and able to do adjacent work. The generalist who can write decent copy, set up analytics, and run a webinar is more valuable at this stage than the world's best PPC specialist.
Hiring too slowly
Founders who've been burned by bad hires swing too far the other way. They interview 30 candidates for every role. They add extra interview rounds "just to be sure." They wait for the perfect candidate who doesn't exist.
Meanwhile, the founders are burning out doing the work that this hire should be doing. Speed matters. For your first 5 hires, you should be able to go from "we need this role" to "someone started" in 4-6 weeks. If it's taking longer, your bar might be unrealistically high or you're looking in the wrong places.
What to actually optimize for
Autonomy
You don't have time to manage anyone closely. Your first hires need to figure things out on their own. Give them a goal and they should be able to work backwards to a plan without you holding their hand. In the interview, ask about times they built something from scratch without clear direction. If they can't give you a specific example, they need more structure than you can provide.
Comfort with ambiguity
At a 5-person startup, job descriptions are fiction. The marketer will end up doing customer support. The engineer will end up doing product management. Everyone will do things they weren't hired for.
People who need clear role boundaries and defined processes will be miserable. Hire people who hear "we don't really know how this should work yet" and get excited instead of anxious.
High standards
Your first hires set the quality bar. If they produce mediocre work, mediocre becomes the norm. If they produce excellent work, excellence becomes the norm. This is more important than specific skills because skills can be learned but standards are contagious.
Look at their previous work. Not their CV - their actual output. The code they wrote. The campaigns they ran. The content they published. Is it good? Not adequate. Good. Your first 5 hires should be people whose work you genuinely admire.
Low ego
In a small team, there's no room for people who won't do work that's "beneath them." The CTO needs to be willing to answer support tickets. The first sales hire needs to be willing to update the CRM themselves. People who need status, titles, and hierarchy to feel motivated will poison a small team fast.
The roles that actually matter first
Every startup is different, but there's a pattern to which hires create the most value early:
First hire: someone who does what the founder can't. If you're a technical founder, your first hire should be someone who can sell or market. If you're a business founder, your first hire should be someone who can build. Don't double down on what you already have.
Second hire: someone who does what the founder shouldn't. You can do the bookkeeping, customer support, and operations. But every hour you spend on that is an hour not spent on product or sales. Hire someone who takes the operational weight off your shoulders.
Third hire: someone who multiplies the first two. A designer who makes the product and marketing both better. A data person who helps sales and product make better decisions. Someone who creates leverage across what you're already doing.
After that, it depends on what's working. If sales is working but you can't deliver fast enough, hire engineers. If the product is great but nobody knows about it, hire marketing. Follow the bottleneck.
How to know if you got it right
Three months after your fifth hire, ask yourself these questions:
- Does the team feel like it's moving faster or slower than before you hired?
- Are you spending less time on things that aren't your core job?
- Would you enthusiastically rehire every person if you had to start over?
- Are people solving problems you didn't even know you had?
If the answer to any of these is no, you have a hiring problem to fix. And the sooner you fix it, the less damage it does. At 5 people, every week with the wrong person costs more than you think.