Founding-Employee fit: know who to hire when 

I recently wrote about founder-market fit—where a founder must authentically understand themselves, their company, and the market conditions in which they’re building. Success here comes from knowing yourself and how you want to (and need to!) run your business given the situation your company is in. 

Of course, success is a result of many things. One of which is likely the people you, as a founder, choose to hire. But that employee profile looks a lot different depending on the stage of your company. They must fit the needs of your company at that time and hopefully, can grow as your company does. 

I’ve seen mismatches during both my time as a founder and as an investor. Here’s how I break down the different stages and the employee fit at each. 

The first 20 employees: know it all, do it all 

This is probably a unique time for your company and you’ll need unique employees to help build it. Your first 20 employees should have an ownership mentality, with the flexibility and grit that helps them adapt to the ever-changing needs of the business. 

Getting office snacks at Coscto, setting up computer monitors, running ad campaigns, negotiating a contract with Amazon—this initial group is your do-it-all crew. They have a bias to action and can seamlessly context switch. At this stage, the company is small enough that these people know just about everything happening and who’s doing it. This is where owners thrive. 

These hires are crucial, and here are some traits I’ve seen founders identify in their initial set of employees: 

• Low ego — no job is too small for this group. And as the company grows, they’ll hopefully have the confidence to not be territorial as it becomes necessary to hand off projects. 
• Mission-aligned — it’s your job to create buy-in across the company’s lifecycle, but it can be especially important early as you’re recruiting employees to join you in an uncertain future. 
• Low activation energy — speed is a startup’s biggest advantage. You want to find people who will jump into a project immediately, instead of needing to ramp up into it. 

But as the company grows, this initial group might get uncomfortable. 

The next 50 employees: specialized-generalists 

Growth is often painful for that first cohort of 20 employees. Roles get more specialized, and the versatile ownership mentality that made them so valuable will need to be focused. Knowledge-sharing also becomes more difficult, where there’s less institutional knowledge and more documentation / processes. The first 20 won’t know everyone, won’t know everything going on, and might have a hard time giving away their legos.

Some of the first 20 will leave. That’s ok! The company’s needs are shifting, and so does the employee profile of the next 50. 

• Find specialized-generalists — at this stage, you’ll still need generalists who can flex into different roles or projects. But they should have some expertise in at least one area (a “t-shaped” person). Think of hiring your first marketer. They know enough to be dangerous across SEO, lifecycle, and content, but might be an expert in the area you think is most important for your business now (like product marketing). 
• Communication and process get more important — silos will naturally form, and you’ll need employees who can navigate those to drive important work forward. Whether it’s working cross-functionally, getting buy-in from executives, or reporting, employees who understand some of the work-about-work can create huge impact while doing the work itself. 
• What doesn’t change? Ownership, action, and flexibility — even though you might lose some of the initial 20 employees, what made them important in the first place remains. Your company is still small enough where things will change rapidly, from roles to context, and having teammates who still embody these characteristics will be key to the shifting needs of the company.

Early in your company’s journey, things might’ve felt more like a free-for-all: everyone doing everything and knowing who’s doing it. This transitional stage is crucial because you want to retain that ethos, but start to build the foundation and structure for scale. 

Beyond 100 employees: the departmental divide 

At this point, there’s likely more structure to organizations across the company. What I’ve seen happen is that top-down communication matures as well—making it easy to know what’s happening across the company. 

Ironically, it can be hard for employees to know everything happening in their own department. There are so many concurrent projects, initiatives, and campaigns that an employee who once knew everything, and everyone, in their department will likely struggle to stay updated on their team’s work. 

At this stage of growth, it can be helpful to: 

• Foster the growth of the first 50 employees — those first 50 employees are crucial to company culture, knowledge, and more. It can be extremely high value to teach them how to navigate a larger org, like ways to deliver information at the right altitude or techniques for managing up. 
• Find people who can operate with some ambiguity — success isn’t a straight line, and as a company grows, teams will be pushing different initiatives to achieve it. As you hire, focus on people who understand what the goals are and bring the experience and drive to set a path to success themselves. 
• Remember, not everyone scales — the employees who got you to this point don’t necessarily possess the skills to take you to the next stage. Often, they think they are. Yes, they’ve learned on the job, have institutional knowledge, and are subject matter experts. But they are usually young, haven’t managed before, and will be recreating the wheel unlike more experienced, growth-minded executives. You’ll have to decide which early employees are worth the investment (short-term pain, long-term scale) versus those who helped you climb the previous mountain but are not equipped for the next. 

As your company scales, so do the structures that enable scale. Finding individuals who can exist within those structures while helping scale them (which is different than establishing them) is crucial for the 100+ employee stage. 

Right people, right time

Your job as a founder isn’t just to build a great product; it’s to build a great company. The people you hire are such an important component of that. 

The goal isn’t to find employees who will stay at your company forever. It’s about finding the right people for the right stage of your company’s journey. By doing so, you’ll build a more resilient, adaptable, and successful startup.