Don’t Botch Your First Numbers Hire

Most companies hire an analyst. What they need is a thought partner.

Most startups have no idea what they’re doing when it comes to making their first numbers hire. They overweight technical skills—SQL fluency, Accounting, tooling and systems—and miss the bigger picture entirely. They think they’re hiring someone to answer questions. But the real value of a great analyst, especially early on, is that they change what questions you ask in the first place.

This hire isn’t about execution. It’s about judgment. You’re looking for someone who can walk into a room of ambiguity and leave with clarity. Someone who knows how to navigate messy data, fuzzy metrics, and incomplete context and still get to something useful. That’s not about tooling. That’s about instinct. It’s about understanding how a business works, knowing what to measure, and being brave enough to say, “This number doesn’t matter. Here’s what does.”

I made this mistake early at Intercom. Some of my first hires were incredibly technical. They could query anything. They built beautiful charts. But they didn’t bring clarity. It wasn’t until later that we hired someone who could challenge assumptions and reframe the way we thought about performance. And have that conversation with the CEO. That hire changed everything.

And here’s the catch: what makes a great hire depends entirely on how your business works. There’s no such thing as a one-size-fits-all analyst. In a product-led company, you need someone who lives in databases. In enterprise up-market SaaS, you need someone with RevOps instincts. Someone who can talk pipeline health and win rates with a VP of Sales. In a marketplace or eComm business, you need someone who thrives on experimentation and iteration; conversion, pricing, and speed of feedback are everything. Hiring a generic “data person” is how you end up solving the wrong problems with beautiful dashboards. Fit matters.

Once you’ve nailed the context, the real differentiators aren’t found on a resume. Curiosity matters more than credentials. The best analysts don’t wait to be assigned projects—they’re already five “why’s” deep by the time you’ve finished asking your first question. They have the business judgment to separate signal from noise. They can tell you when a metric is lying. And they can communicate clearly—because if your Head of Sales doesn’t understand the insight, it might as well not exist.

There are also a few easy red flags. If someone needs perfect data to get started, they’re not ready for startup life. If they build dashboards and disappear, they’re not your person. And if they never ask about your customers, business model, or goals—they’re thinking like a technician, not a partner. And what you need at this stage is a partner.

I’ve hired for over 50 analytical roles in the last decade, and I’ve interviewed hundreds of candidates. I’ve tried it all: take-home tests, live case studies, fancy frameworks, behavioral questions. Most of it’s noise. Today, there’s only one question I really trust to give me signal.

I ask: “Walk me through an analysis you did, end to end.” Then I spell out what I mean. I want to understand where the idea came from, why they chose to work on it, how they structured the analysis, what blockers or aha moments they encountered, what the recommendation was, and what impact it had on the business.

It’s a mouthful. So I repeat it if needed and tell them to jot down the sub-questions. Any analyst worth hiring will light up and run with it. That’s when the conversation gets good. And that’s when your job begins— to listen analytically. Ask follow-ups. Don’t let them skip steps. Be genuinely curious. Try to learn something. It’s the best way to evaluate how they think.

As they talk, I’m listening for a few things. Can they tell the story to someone who wasn’t there? Were they intentional about choosing the project? Did they break down the problem with structure and clarity? Did they face blockers? And more importantly, did they push through them? Was there a real insight? Did it lead to a real decision? Did the business change as a result?

If they walk you through a project that’s still in flight and doesn’t have impact yet, ask for another one. If they can’t name one with clear business results, that’s your answer. Junior candidates might reasonably say the project was assigned. That’s fine. But for senior candidates, I want to see that they’re originating work—not just reacting to it.

The rest of the interview, I keep it simple. I’ll ask the same question again. Maybe with a twist. “Tell me about an analysis you came up with yourself.” Or, “Tell me about a time your recommendation didn’t pan out.” What matters is that we’re in the zone where the real work happens: context, methodology, insight, narrative, and impact. That’s the job. And this one question tests all of it.

When you get this hire right, it’s one of the most leveraged decisions you’ll ever make. Because the best analysts don’t just analyze. They provoke. They reframe. They change how the company sees itself. They don’t just give answers—they give you better questions.

Don’t botch the hire. Get it right, and your entire company will be sharper for it.