Context

When I joined the Career as a Platform (CaaP) team at Stride, I found a group that had been working for eight months without senior product leadership. The project had a meaningful purpose - helping high school students who weren't heading to college find pathways to good jobs. Despite having 80 talented people on the team, they hadn't released any features and were dealing with growing technical debt.

The platform was designed to guide students through career assessments, learning paths, certification preparation, and job placement. But somewhere along the way, the team had lost sight of why they were building what they were building.

Challenge

As I got to know the project, I saw a team caught in reactive mode. They were holding design sessions on Zoom while developers coded in real-time. Stories were being written in just thirty minutes. People were working long hours with no time to think or validate ideas. Their original three-month launch date had long passed, leaving them with reduced scope and technical problems.

What really stood out was how disconnected the work was from its purpose. When I asked why they were building specific features, the team would often pause, realizing they didn't know. They were just checking boxes without understanding the customer needs or business goals.

Approach

Instead of pushing for faster delivery right away, I focused first on helping the team reconnect with their purpose. I created simple documentation and training on basic product development practices. I brought together people from product, design, and project management for in-person training to get everyone on the same page.

Next, I worked on improving how we planned and prioritized work. The team had been completing only about 50% of what they committed to in each sprint, often picking stories randomly. We also made time to fix technical debt by creating proper testing frameworks that would support continuous deployment.

Understanding we needed both immediate structure and longer-term direction, I built a six-month roadmap using practical tools: Miro for brainstorming, Aha! for planning and story development, and Jira for day-to-day work. This helped the team see how their daily tasks connected to bigger goals.

Outcomes

In five months, we launched two releases and completed half the stories for two more. Beyond just the deliverables, I saw a real change in how the team worked. They shifted from random development to focused, value-driven work. Our investment in technical foundations improved deployment confidence and reduced bugs.

Most importantly, the team transformed from a group running on caffeine and late nights to one working with purpose at a sustainable pace. Better planning and prioritization meant they delivered more value while working fewer hours - showing that thoughtful leadership works better than just pushing for speed.

Key Takeaways