Six Months as Employee Number Four: What Nobody Warns You About

When I accepted the offer to become employee number four at our scheduling startup, my friends who worked at big companies were a mix of impressed and worried. I had a decent salary, a small slice of equity, and a job title that included the word "head" even though I would be heading exactly myself.

Six months in, I wrote a long note to myself about what had surprised me. I am sharing an edited version, because I wish I had read something like it before I signed.

Your job description is a rough guess

The role was "Head of Marketing." In my first month, I also answered support emails, rewrote onboarding screens, helped choose a payroll provider, and drove to a print shop to pick up trade show banners because nobody else had a car that day.

None of that was a problem, but it meant my actual marketing work happened in fragments. I eventually blocked Tuesday and Thursday mornings on the shared calendar as "marketing only." The founders respected it once they saw it written down. Before that, everyone assumed I was always available, because, honestly, I had been.

You inherit decisions you would never have made

The company had a name, a logo, a pricing model, and a homepage before I arrived. Some of those things I loved. The logo I did not. It was a green clock that looked a bit like a broccoli.

I spent my first month wanting to fix everything at once. A wise friend told me to pick only one thing to change in my first quarter and earn trust with it. I picked the homepage copy, because I could show results within weeks. The logo is still the broccoli clock, and I have made peace with it.

Equity feels different on a bad day

On good days, the equity felt like a lottery ticket. On bad days, when a big customer left or a fundraising meeting went nowhere, it felt like an IOU from a company that might not exist next year.

I found it helpful to do the honest math once and then mostly stop thinking about it. I estimated what my shares would be worth in three realistic outcomes: shut down, modest acquisition, strong growth. Two of the three were close to zero for me. Once I accepted that, I could judge the job on what it was teaching me and paying me today.

Small teams amplify everything

With four people, one person's mood sets the temperature for the day. When our CTO was stressed about an outage, everyone felt it. When our CEO came back from a great customer call, the whole room lifted.

I learned to say small things out loud that in a bigger company would go unsaid: "I am tired today, it is not about you," or "That demo was great." It sounds trivial. In a team of four, it changed how we worked together.

Would I do it again

Yes, without hesitation, but with clearer eyes. I would ask in the interview what the founders expect me to stop doing in six months, not just what to start. I would set my calendar boundaries in week one, not week eight.

And I would bring my own car to the next trade show, because somebody always has to pick up the banners.