How do you eat an elephant? One bite at a time. 

Building a customer success (CS) department from the ground up in a startup feels exactly like that – massive, slightly terrifying, and impossible to swallow whole. 

When I tell people I’m the Head of Customer Success at a hospitality tech startup with only 19 employees and a CS team of three (including me), their eyes usually bug out. But early-stage CS is a different animal entirely. You can’t just copy-paste a Series C playbook and expect magic to happen.

In this article, you’ll discover why the big-company playbook fails in a 19-person startup and how to navigate the "messy middle" of building a department from zero. We’ll cover the three pillars of early-stage success: 

  • Being ready
  • Being resourceful
  • Being resilient 

Why early-stage customer success is different

When you're the first CS hire or tasked with building the function, your first job isn't actually to build, it's to learn. 

You've got to be ready for the fact that there's no documentation, limited processes, and a whole lot of urgency. The temptation is to start "doing" immediately to prove your value, but that's a trap.

If you take a big-company playbook and apply it directly to a tiny startup, it's not going to work. Those playbooks assume you've got a well-oiled machine, mature segmentation, and a dream tech stack. In the early days, you don't have any of that. 

You've got to be ready to dig into the dirt before you start planting seeds.

A realistic first 30 days

Your first month should be an internal and external "listening tour." You need to ground yourself in what’s actually happening, not what the product pitch says or what you assume should be happening.

Internally, you need to talk to everyone. If you've got 20 or 40 people, you can meet them all in a month. Understand their goals, their KPIs, and their frustrations. This is how you gain cross-functional buy-in and credibility from day one. 

You’re not just learning about the business; you’re building human relationships that you'll need later when you start making big asks.