Demo Days: What Four Years of Fast Partnership Taught Us
This post highlights work I was proud to be part of at American Family Insurance. Details of the Demo Days initiative were made public with executive approval in November 2021. At the time, it represented a novel approach within the insurance industry and has since been featured in industry publications, at conferences, and in more than one winning award submission highlighting leaders involved with the work.
Most of my posts share the view from the pitching side. This one’s different, here’s what it looks like when design leadership has place at the other end of the table:
Four years. 177 vendor solutions evaluated. 14+ pilots launched. Millions saved. And one big lesson learned: Fast innovation doesn’t require chaos. It requires design.
When we launched Demo Days in late 2019, we weren’t trying to run a cool event, we were trying to solve a hard problem: how to bring external capabilities into a traditional organization without slowing down. We built a simple system: bring in start-ups quarterly, vet them against business priorities, and test what makes sense.
The concept worked. Over the course of four years, we evaluated 177 vendor solutions, leading to 14+ pilots that drove meaningful cost savings, efficiency gains, and gave customers more control over their claims experience.
Now, looking back, I’m reflecting on three lessons my team and I learned along the way.
LESSON 1: STRUCTURE ENABLES BETTER DECISIONS
Most carriers were still scheduling demos while we were wrapping pilots. But the real power of our system wasn’t just speed, it was the quality of our decisions.
When the Chief Claims Officer and I co-designed the Demo Days Scoresheet, we didn’t just build a tool, we created a shared framework for how to evaluate progress. One that made room for more than just tech specs and business cases, and included something often left out of the room: design. Experts in value creation, human behavior, and experience design had an equal seat at the table.
The scoresheet gave everyone a shared language, making space for more collaborative conversations. Conversations that resulted in fewer blind spots, faster consensus, and smarter outcomes.
Designing the structure gave us clarity. And clarity made better decisions possible.
LESSON 2: INNOVATION IS AS MUCH ABOUT WHAT YOU DON’T BUILD
Some of our best wins weren’t what we launched, they were what we walked away from.
We sunset an internal drone inspection build, saving $2M and gaining a better solution through partnership
We avoided duplication by getting clear on the value proposition behind each start-up, a practice that saved us from testing competing solutions more than once
We focused on solutions that scaled across lines of business, not niche tools with short lifespans
Innovation isn’t about volume, it’s about value. Demo Days helped us protect our time, our budget, and our teams from distractions disguised as opportunity.
LESSON 3: CULTURE IS THE REAL INFRASTRUCTURE
By the end of Demo Days, I’d moved from the Digital Transformation Office into the Claims organization, becoming the first Director of Strategic Design under the Chief Claims Officer. That shift wasn’t just a title change, it was proof that the work mattered.
Innovation didn’t live on the fringe anymore. It lived inside the business.
And it changed the culture. We shifted from "Should we partner?" to "How fast can we test it?" From "Who owns this?" to "Who needs this?"
The Demo Days model helped Claims become a place where innovation was expected, not exceptional.
Looking back, we didn’t just test vendors. We tested a new way of operating. And it worked.
Demo Days was never just about speeding up pilots. It was about building an innovation muscle inside a 90-year-old mutual insurer. One that could flex across platforms, teams, and even brands — without ever losing sight of the customer.
