Right now, three of you can agree something in one Slack thread and move on with your day. Nobody wrote it down because nobody had to, you know who to ask about what. That stops working as you add people, because the new person doesn't have the same knowledge in their head that the rest of you do. 

Two things matter from here on: the system you build, and who you hire into it.

Whoever you hire between employee six and ten matters more than people realize – they either reinforce whatever culture already exists, or fight it. At that size, one person's habits and blind spots become the team's default. Darren has watched this pattern across many companies.

Ask any founder if the team feels cohesive, and most will say yes, but few have any real benchmark for what that's supposed to look like. Here is one benchmark: GitLab scored in the top decile of McKinsey's Organizational Health Index - tested against more than 2,500 organizations and 8 million employees - with no offices and colleagues who'd never met in person. Great culture doesn't require an office.

For the avoidance of doubt, location shouldn't decide who joins your team. Fit should.

In today’s world hires should be: comfortable defaulting to public channels over private ones, willing to write a decision down even when it feels obvious, fine with written updates replacing half your meetings. 

Some people find that liberating. Others find it exposing, and work around it instead.

Systems are what let a team scale past five people without breaking. They're also what makes AI a useful. If you want Claude to help you with answers, you need to point it somewhere. Otherwise, what do you expect you're going to get?

A good system gives you options: hire wherever the best person is, and staff however makes sense — fractional, part-time, full-time — because the knowledge lives in the system, not with someone in the office next door.

Darren Murph has spent over two decades building systems for the workplace. He led workplace strategy at GitLab as it scaled from a start up to more than 2,000 employees across 65-plus countries with no central office (andwrote about that experience in his book, DISTRIBUTED).

Twenty people arrives faster than most founders expect — one strong hiring push, or a single raise, and you're there. If the sytem hasn’t been built, you’ll be in it over your head.

In this session, Darren will go through both culture and systems and explain what a five-person company should build now, and who to hire into it, so that a fractional expert or an AI tool is useful from day one, and your next hire strengthens the team instead of working around it.

Worth reflecting on before the session:

• If your co-founder disappeared for a month, how much of what only they know would disappear with them?

• If you brought in a fractional expert for five hours a week tomorrow, would they be useful by day two, or spend a month just learning how you work?

• Does your last hire default to a public channel or a private message when they're not sure? What does that already tell you?

Darren Murph was named an “oracle of remote work” by CNBC and included in the Forbes Future of Work 50. He led workplace strategy and operations at GitLab, scaling the world's first fully distributed company to IPO, and later founded Page 52 Consulting, advising organizations including Ford, Dropbox, and Zillow. He is the author of several books on remote work, including his newest, DISTRIBUTED.