Context

In the summer of 2015, I arrived at Collective Health's San Mateo office for what was initially planned as a brief four-day information architecture consulting engagement. The company had just secured a promising round of funding and faced the daunting challenge of scaling quickly – from 100 to 30,000 members in just six months. What began as a focused assignment evolved organically as I started asking questions about their communication practices and the human challenges of scaling so rapidly. These conversations resonated with the leadership team, and they made the decision to expand my role far beyond the original scope.

This unexpected pivot became a moment of professional reflection for me. While the technical aspects presented interesting puzzles to solve, what truly captured my attention was the human dimension of their work. Health insurance intersects with people's lives at moments of vulnerability and uncertainty. Behind every member number was a person navigating the complexities of health decisions, and I recognized an opportunity to transform those experiences through thoughtful system design.

Collective Health was pursuing what seemed almost unattainable at the time – 70% customer satisfaction in an industry where disappointment and frustration were accepted as inevitable. This aspiration aligned perfectly with my core philosophy about technology – that it should serve human needs first, with technical elegance following as a natural consequence of that human-centered approach.

Challenge

This project was complicated in ways that went beyond typical technical work. Yes, we had to deal with HIPAA compliance and healthcare regulations, but the real puzzle was more human: how do you scale personal, caring customer service when growing so quickly?

I found myself wrestling with questions that made me grow as a leader: How do we create systems that protect sensitive information while making it easy for people to help others? How do we keep the human element while using technology to scale? I'd faced similar questions before, but never with such high stakes or at this scale.

Approach

I've always approached consulting with two simple goals: understand what the business truly needs (not just what they ask for), and give clients the tools to succeed without me. Some might think it's strange to try to work myself out of a job, but this approach has always led to better relationships and more meaningful work.

Over six months of regular visits to San Mateo, I learned the ins and outs of health insurance plans and regulations. We built three connected systems: a knowledge framework in Confluence, a customer service integration platform, and a HIPAA-compliant bug tracking system. Each part needed to balance technical requirements with human needs. The knowledge system wasn't just about storing information – it was about making complex health plan details make sense to the people helping members.

What began as technical consulting naturally expanded into business transformation. I spent time with teams across the company, helping them communicate better and improve their workflows. This experience reinforced something I've always believed – technical solutions only work well when they support the humans using them.

Outcomes

The results were better than any of us expected. Collective Health reached 95% customer satisfaction, far beyond their initial 70% goal. But numbers don't tell the whole story. We created systems that let customer service representatives focus on connecting with people instead of fighting with technology. We built security measures that protected sensitive information while still being intuitive. Most importantly, we helped create a workplace where technology supported human connections rather than getting in the way.

We delivered the project under budget and ahead of schedule, but the real success was in how it changed how teams worked together. The solutions we built became the foundation for Collective Health's continued growth in the years that followed.

Key Takeaways