Inside my first 90 days as Head of People at a startup

June 10, 2025 | Edition #9

Join me for a free, invite-only panel discussion:

In this session, Chris and I will explore what it means to run People Operations like a product—starting with understanding your business model and what problems you’re solving. You’ll leave with tactical tips on aligning People priorities with business strategy and employee feedback.

Register for the panel discussion

A few months ago, I joined Kit as Head of People Operations.
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That meant rolling out my tried and true leader onboarding plan—for myself.

In my first 90-days as a new leader, I want to understand 3 key things:

1. What’s the business trying to accomplish?
2. How performant is our People Ops function today?
3. What do our employees (aka our “users”) want to see?

To help answer these questions, I use three inputs:

• A business evaluation model that focuses on gaining awareness of the market we're operating in, learning about our product and business model, and assessing the caliber of our team. For a deeper dive on this model, register for the Behind the Scenes of a Product-Led People Team panel discussion.
• A people ops org diagnostic to understand where our function sits on a maturity curve.

• A "90 in 90" listening tour—90 conversations with full-time team members in my first 90-days. Structured, but conversational.

Here are some of the questions that I ask in my listening tour:

Building Rapport

• Tell me about your career story? How did you get to where you are today?

Lived Experience

• If <1 year with the company: Why did you choose to join [company name]? How has your experience thus far compared to your expectations and aspirations when you chose to take the role?
• If >1 year with the company: Why do you choose to stay with [company]? What accomplishment are you most proud of from your time with [company]? How would you describe your overall experience with [company] in 3 words?
• What value do you see us live into the most? Least?

Roadmap Planning

• If you had magical powers and could change up to 3 things at [company], what would you change and why?
• What are you really hoping to see from the People Operations team in the next 6-12 months?

Given my background in customer success, I take a pretty unique approach to tracking these conversations... I use a product management tool called Productboard to ingest and prioritize user insights and business goals.

In Productboard, I can see how many people raised a specific problem, whether or not that aligns to our business goals, and more. All the inputs I need to make prioritizations decisions and develop a roadmap.

Not a static one. A living, evolving product plan for People Operations—based on what our business needs, what our people are asking for, and where we actually are today.

Each initiative ties to business goals — I like to ladder up to company goals using either an AED or TEAM framework — and gets tracked like a real product—features, releases, feedback loops and all.

It’s not perfect. But it’s focused. Grounded. And real.

If you’re stepping into a new People leadership role—or just want to reset how you lead—start here:

Listen first.
Triangulate the business, function, and users.
Then prioritize and build, deliberately.

People Ops isn’t about what you want to launch.

It’s about solving the right problems, at the right time, in the right way.

That’s what the first 90 days are for.

📌 The Four-T Playbook: Tip, Trick, Tactic, or Template

Every edition, I’ll share a proven insight to help you scale faster, smarter, and more efficiently.

👉 Tactic: To keep a pulse on team member sentiment and needs, run listening tours with structured, role-specific questions. Treat them like user research.
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For ongoing conversations, instead of "stay interviews" which can feel sterile or forced, run either a "coffee and conversation" series or host recurring drop-in office hours or couches where you ask a few questions after answering a few questions.

Final thoughts:

This edition was a little different.

Instead of sharing a framework or playbook I’ve refined over years, I walked you through what I’m doing right now—the real conversations, diagnostics, and decision-making behind my first 90 days as Head of People at Kit.

Was that helpful? Do you want more behind-the-scenes like this? Or do you prefer more strategic and theoretical topics?

I’d love to know what you want to learn from me. Hit reply and tell me.

Until next time,
Melissa

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