Trello

Head of Design • 2021-2023

Snapshot

✨ Highlights

Grew design from ~12 to 25+ designers and managers
Operationalized experience quality across all squads and teams
Delivered a vision for the future of Trello
Developed a design team charter, purpose, and values

🎯 Impact

Increased CSAT from 86% to 89%
Increased our internal Proud to Ship metric from 45% to 55%
Increased revenue through the introduction of Premium and Enterprise plans

Case studies

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1. Operationalizing experience quality

I led an effort to operationalize experience quality across Trello. This included clearly defining experience quality OKRs, setting expectations for squads and teams, and delegating ownership of key results across the organization. This effort directly contributed to a 3% increase in CSAT and a 10% improvement in our internal “Proud to Ship” metric.

Trello quality objective Our quality objective focused on delivering consistent, reliable experiences

Trello quality key results Key results were measured through CSAT, performance metrics, and accessibility scores

2. Design team charter

When I joined Trello as Head of Design, the team was growing fast. There had been significant recent turnover, and many new designers were joining the team. To ensure we retained the incredible culture the team had built over previous years, I planned and led a workshop to define our purpose, values, and goals. The output of this workshop was a design team charter that became a cornerstone of our culture for the next 3+ years.

Team charter workshop goals Our goal was define the unique purpose and values for the design team

Trello design team values Our design team values became a bedrock of our culture for the next 3+ years

3. Visual roadmap

During a period of rapid new feature development, our product experience started to fragment. To connect the dots across squads and inspire the organization, we tasked a small cross-functional team with delivering a visual roadmap. This visual roadmap became a key artifact for the organization to develop a shared understanding of the product vision and align around the future of Trello.

Trello visual roadmap Our visual roadmap connected the dots across squads and inspired the team

4. What if, Trello?

Building off the success of our visual roadmap, we set out to deliver a more ambitious vision for the future of Trello. What If, Trello? asked the design team to imagine not what Trello is today, but what Trello could become. We used this exercise not only as a way to inspire and motivate our immediate team but also to generate a set of ideas that provoked new thinking and conversations with our executive team and founders.

The call to action I shared with the team

A more conversational card back

Exploring cross-flow between Trello and Confluence

A provocative new approach to Atlassian’s product suite

5. Design leadership roles & responsibilities

During my time leading design at Trello, I was responsible for defining the roles and responsibilities for the design leadership group, which was composed of both managers and ICs. With an organizational emphasis on experience quality, we explored new ways to empower principal designers to raise the quality bar across the organization. This model clearly defined those roles and responsibilities.

Design leadership roles & responsibilities

📫 Want to learn more about my work or go deeper on a case study? Get in touch.