Have you ever felt like your support team is maturing faster than your systems could keep up?

In this episode of Live Chat with Jen Weaver, I’m talking with Alex Armstead, Principal Business Operations Manager at Clever (yes, the Clever that powers classrooms for 60% of U.S. schools). Alex has spent the last nine years helping his team grow without burning out, checking out, or losing what made them special in the first place.

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What we get into this episode:

This one’s a blueprint for support leaders, ops pros, and anyone wondering how to keep people engaged and growing.

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You’ve got great people. They’re growing, your team is scaling, and the work is getting more complex. But the systems that support your team? They’re still stuck in “early-stage startup mode.” Career development looks like waiting for a promotion. Feedback gets collected but not acted on. And the only time culture gets addressed is when someone quits.

If you’ve ever looked around and thought, “We’re running too fast to keep this sustainable,” you’re not alone. And you’re not stuck. This week’s guest, Alex Armstead, has been through that evolution firsthand. Over nearly a decade at Clever, they’ve helped the team move from scrappy to strategic, all without losing what made it special in the first place. Here’s how.

Alex shared a step-by-step framework for building a team where people want to stay, grow, and lead—without burning out or hitting invisible ceilings.

Not every individual contributor (IC)  wants to become a manager. That doesn’t mean they should hit a ceiling.

Clever’s framework outlines how team members can grow laterally, take on strategic projects, or represent support cross-functionally without needing a title change. This includes:

Before trust can thrive in real-time, you need to understand how people are experiencing leadership. Clever uses Culture Amp to collect anonymous feedback on:

Data is grouped by tenure, role, and identity (never fewer than four per cohort) to protect anonymity and reveal trends.

Collecting feedback isn’t enough. After each survey, Alex’s team forms action committees comprising managers and ICs to review themes, set priorities, and co-create solutions. Each initiative gets a sponsor to move it forward.

Instead of waiting for hard questions to show up in 1:1s, Clever creates space for them in monthly team-wide Q&As. Team members can submit questions anonymously, vote on others, and hear leadership respond live or in follow-up.

It’s about building transparency into the culture, not just reacting when things go wrong.

Clever doesn’t wait for burnout to fix what’s broken. Each subteam runs a postmortem right as the peak tapers off, while the pain is still fresh. They identify friction points, synthesize them across teams, and transform them into focused projects for the next cycle.

Clever’s support org is scaling, but not at the expense of its people. By embedding trust into his operations, Alex and his team have created a culture where:

Whether you’re leading a team, mentoring mid-level managers, or just trying to stop reinventing the culture wheel every quarter, this framework is a solid starting point.

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See you next time!

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