The First Hire Every First Operator Should Make

The wrong hire will slow you down. The right one makes everyone faster.

You just joined an early-stage startup as the first finance hire. Or maybe the COO. Or the person trying to wrap their arms around how the business works. You are buried in board decks, funnel metrics, usage reports, forecasts, investor updates, pipeline tracking. You are duct-taping together metrics from six different tools. Nothing reconciles. Everything is urgent.

Your instinct is to hire an analyst.

I had the same instinct when I joined Intercom. In fact, I hired multiple analysts. That was a mistake. It helped in the short term, but it made everything harder in the long term. It slowed me down. It slowed the company down. And it took me a few painful years to realize what the first hire should have been instead.

Let me explain.

The Common Mistake

The mistake most first operators make is they try to hire their way out of ad hoc work. You have too many things to do, and analysts feel like the logical answer. You tell yourself, I need someone to own the funnel report. To maintain the forecast. To track sales pipeline. To pull usage metrics. To help me get my time back.

So you bring in someone who knows SQL. They can run your spreadsheet. They can pull a query. You feel some relief.

But what you have really done is hire someone to stand on the same shaky foundation that you are already standing on. The spreadsheet still breaks. The data still changes. The business gets more complex. And now you are not just managing your own chaos, you are also checking someone else’s work. You become the bottleneck. Your analysts become less effective. And the whole thing starts to slow down.

The Pain You’re Actually Solving

The real pain is not that you have too many things to do. It is that you have no clear, durable, shared definitions for how your business works.

As a first operator, you have to move fast. You cut corners. You do whatever it takes to get the board deck out, to prep for fundraising, to build the forecast. You create janky systems that work for the moment. You pull from Stripe exports and Salesforce CSVs and usage data and pray that it all kind of matches up.

But the cost shows up later. In meetings where no one agrees on what the number means. In dashboards that contradict each other. In endless rework. In time spent debating if the number is correct instead of talking about what it means.

What you actually need is someone who can bring clarity. Someone who can say, let’s step back. Let’s define this properly. Let’s design it in a way that reflects how the business actually works. And let’s do it in a way that does not break every two weeks.

The Right Hire: System-Building Over Speed

You do not need another spreadsheet jockey. You need someone who can build the foundation.

They might be called an analytics architect. They might just be a very strong analyst who has built durable data systems before. The title is not important. The mindset is.

The right hire is not just curious and insightful. They are hyper-organized. They are methodical. They over-communicate. They write things down. They care deeply about definitions. They are a little bit obsessive about process. They think in terms of tables and schemas. They want to know how ARR is defined and why. They want to know how revenue maps to billing and collections and what logic should govern that transformation.

They are comfortable leading conversations across functions. They are not afraid to get on a call with sales and say, here is how I think we should define opportunity stage. Or to sit with product and talk through how we measure active usage. They build trust because they care more about getting it right than looking smart.

What Success Looks Like in the First 90 Days

In their first ninety days, they are not just pulling reports. They are building the foundation the rest of the company will stand on.

They pick the most important and painful reporting problem, like ARR, and they build what we call the mega table. One clean, well-modeled table that becomes the source of truth for a metric the company lives and dies by.

They talk to everyone. They figure out what sales means when they say churn. They understand how product defines an active user. They map those inputs to the right logic. And then they build a structure in the data warehouse that reflects those definitions clearly and durably.

They create something reusable. Something that scales. Something you can plug into dashboards, investor updates, or board decks without asking, “Wait, where did this number come from?”

It Might Feel Harder at First

Here is the honest truth. Hiring this person will not immediately take work off your plate. In fact, at the beginning, it might feel like you are doing even more.

You will still be deep in the weeds. Still doing your own analysis. Still building decks. Still prepping for the board. Because in the early days, you are helping this person ramp. You are giving them context. You are helping them understand the product and the quirks in your billing system and the weird edge cases in your CRM.

But once they become productive, the tide turns. The system starts to run. And then, everything flips.

You go from doing the work to reviewing the output. From defining the numbers to interpreting the insights. From managing chaos to managing clarity.

It is a short-term investment with long-term payoff. And the payoff is massive.

How to Interview or Evaluate This Hire

You are not hiring them for SQL tricks. You are hiring them for how they think about data structure.

One way to test that: give them raw data. A Stripe export, for example. Then ask them to design a schema or table that makes it easy to query monthly recurring revenue and churn.

You are not looking for the exact same business logic you use. What matters is how they approach the problem. Do they think through how this data will be used? Do they anticipate edge cases? Do they name columns clearly? Do they group things in a logical way? Can they explain their rationale? Can you imagine using their table in your actual reporting?

This kind of exercise tells you way more than a list of dashboards they have built or a notebook full of SQL.

The Leverage of Getting This Right

This is one of the highest leverage hires you can make.

Hire the right person, and every analyst you bring on afterward becomes five times more productive. Because they are not building things from scratch. They are plugging into a system.

You become more productive too. You stop checking their math. You stop debugging queries. You stop wondering whether the number in Slide 7 matches the one in the dashboard.

You stop arguing about whether the metric is correct. You start talking about what it means.

And most importantly, you stop being the only person who understands how the numbers work.

What I’d Do Differently

At Intercom, I made this mistake. I hired analysts first. Because I was overwhelmed. Because I thought that would save time.

It did not. It slowed me down. It slowed us down. I had to stay in every conversation. I had to keep checking everything. We kept reinventing the same reports because we never fixed the underlying structure.

What I needed was someone who could bring clarity. Someone who could define how the business worked within the data… someone who could build a foundation others could stand on.

At Equals, and now through working with other startups, I’ve learned to spot this hire early. They are rare. But if you find them, they will change everything.