Liam
Trello
Case study
Trello was growing fast but its experience was fragmenting. Our team had nearly doubled in size while simultaneously experiencing significant turnover as many original Trellists moved on to new challenges. Meanwhile, rapid feature development across multiple squads aimed at monetizing our established user base was making our product experience inconsistent and negatively impacting our users.
We faced a multi-part challenge: scale our team, operationalize design quality, and grow our bottom line, all while preserving what made Trello special.
🎯 Impact
- Operationalized experience quality - Increased CSAT from 86% to 89% and our cross-functional “Proud to Ship” metric from 45% to 55%
- Built lasting team culture - Developed a design team charter, purpose, and values that became the bedrock of our culture for 3+ years
- Connected fragmented work - Delivered a visual roadmap and vision for the future of Trello that aligned squads and inspired our team and stakeholders
- Drove revenue impact - Contributed to increased revenue through revamped Premium and Enterprise plans
Snapshots
📢 Atlassian recently launched Trello 2.0, reflecting many of the foundations we established during my tenure.
Operationalizing experience quality
Experience quality, historically Trello’s strength, was slipping. We were in a feature race and squads were optimizing for speed over quality. There was no clear definition of what “quality” meant across the organization and we lacked incentives for teams to prioritize it.
Approach
I led an effort to operationalize experience quality across Trello by treating it like any other core business metric. Through a shared cross-functional OKR, I incentivized teams to make quality a priority. We set clear expectations for squads and delegated ownership of quality key results across the organization.
Our quality objective focused on delivering consistent, reliable experiences
Key results were measured through CSAT, performance metrics, and accessibility scores
Impact
This effort directly contributed to a 3% increase in CSAT and a 10% improvement in our internal “Proud to Ship” metric. More importantly, quality became an integral part of how every team measured success. By making this a cross-functional goal rather than a design-only initiative, we distributed ownership and made quality everyone’s responsibility.
Design team charter
With the team growing fast and significant recent turnover, many new designers were joining without understanding what made Trello’s design culture unique. Meanwhile, tenured designers were concerned we were losing what made Trello such a special place to work. We needed to preserve the most important parts of the unique culture the team had built over previous years while evolving it for continued success.
Approach
To preserve and evolve what made our team unique, I planned and led a charter workshop where our team defined our purpose, values, and goals together. We highlighted the unique attributes of our team that we wanted to keep, while allowing space for newer ideas to emerge about how we hoped to work together moving forward.
Workshop mission
Roses, Buds, and Thorns
Our design team values became a bedrock of our culture for the next 3+ years
Impact
This design team charter became a cornerstone of our culture for the next 3+ years. Team members still reference these values in design critiques, hiring conversations, and strategic decisions.
🔗 Learn more about this workshop
Visual roadmap
During a period of rapid new feature development, our product experience started to fragment. Multiple squads were building features in isolation, and Trellists struggled to see how individual projects connected to a broader vision.
Approach
To connect the dots across squads and inspire the organization, we tasked a small team with delivering a visual roadmap. This roadmap helped teams across Trello understand what we were building, why it mattered, and how individual features connected to larger themes.
Sample outputs
Just a few of the many vignettes from this effort
Our visual roadmap connected the dots across squads and inspired the team
Emphasis was placed on cross-platform experiences and collaboration
We leaned into a more conversational, modern card back
Impact
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. It also acted as a stepping stone into more ambitious envisioning efforts.
What if, Trello?
Building off the success of our visual roadmap, we wanted to push beyond incremental improvements and shine a light on Trello’s brightest possible future. We needed to inspire the team to think bigger while generating ambitious ideas that could spark new conversations with our stakeholders and executive team.
Approach
I challenged the design team with an invitation to play. The question was simple: Putting aside today’s constraints and the fear of failure, what could Trello become? This exercise asked designers to imagine many different possible futures for Trello, creating concepts that would inspire our team and provoke entirely new ways of thinking about our experience and product.
The call to action I shared with the team
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
Impact
While not every concept was designed to ship, this exercise fundamentally changed how we approached the future of Trello. It gave the team permission to think bigger and provided leadership with a vision of Trello’s potential beyond its current form. The lasting impact of this creative effort is still showing up in Trello’s most recent evolution into a more modern, connected experience.
Design leadership roles & responsibilities
As our design team scaled to 25+ people, we needed new models for design leadership that went beyond traditional management hierarchies. With an organizational emphasis on experience quality, we needed ways to empower our most experienced individual contributors to drive impact across the organization.
Approach
I developed a design team attributes framework that clearly defined roles and responsibilities for our design leadership group, which included both managers and senior ICs. This model recognized that leadership comes from expertise and impact, not just title, and gave senior ICs clear pathways to influence quality and culture across teams.
Design leadership roles & responsibilities
Impact
This framework empowered lead & principal designers to drive quality and culture alongside managers, creating multiple opportunities for leadership influence. It helped us scale design leadership as the team grew while ensuring our most experienced designers could make organization-wide impact.
Reflections
Leading design at Trello reinforced that scaling isn’t just about adding people but creating an environment that helps teams do their best work. The frameworks we built didn’t just survive my time there; they became part of how Trello operates to this day.
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