Jira Align Capacity (designing in captivity)
In 2023, I joined Atlassian’s Enterprise Agility team, tasked with helping customers bridge the gap between business strategy and tactical execution. Our core product, Jira Align (formerly AgileCraft), was an acquisition product with roots in a completely different design system, codebase, and content management system (CMS). Coming from the sleek and unified world of Jira Software, stepping into Jira Align felt like entering an entirely new dimension—one filled with chaos, misalignment, and countless hurdles to overcome.
First impressions
Jira Align was a beast comprised of 500+ legacy features. Every bit of terminology in the tool was customizable, making consistent documentation nearly impossible. As designers, we’re taught to strive for elegance, efficiency, and delight, but these standards often felt out of reach within our technical constraints. My initial goals were ambitious:
Bring Jira Align up to Atlassian’s design and accessibility standards.
Migrate all content assets and practices to Atlassian’s CMS and workflows.
Build new features that felt cohesive within the Atlassian ecosystem.
Tech debt challenges
Working on Jira Align was a lesson in perseverance and adaptability. Like slaying the medusa, every problem solved revealed deeper, thornier issues. The product’s non-existent design system clashed with Atlassian’s modern standards, requiring significant overhauls for even minor updates. Deep explorations often resulted in solutions that we couldn’t fully implement due to technical constraints. Users of enterprise products demand precision and reliability, but delivering these within Jira Align’s ecosystem was an uphill battle.
Design principles
Despite these hurdles, I leaned heavily on one of Atlassian’s core values: "Be the change you seek." I adopted a few principles to stay focused and deliver as much value as possible:
Progress over perfection: While I naturally gravitate toward high standards, I learned to embrace “good enough” solutions. Focusing on what’s valuable and feasible now drives forward momentum.
Listen with empathy: Customers, partners, and teammates alike struggled with Jira Align. By actively listening, I developed solutions that addressed external and internal pain points.
Keep it simple: With so much complexity, I prioritized breaking down workflows and information into digestible steps, guiding users with clarity and intention.
Lessons learned
Resilience: Tackling systemic problems requires persistence and the ability to adapt to shifting priorities. Learning to pivot quickly—and with optimism—was key to maintaining momentum.
Process: Migrating and maintaining legacy systems taught me that preventing, and clearing, technical debt is foundational for future innovation.
Patience: Unlike startup environments, enterprise design requires patience, diplomacy, and collaboration across many layers of stakeholders. Quick wins matter, but the ultimate goal is systemic improvement.
Final thoughts
I suppose every designer eventually faces a period of hardcore maintenance work or constraints so tight that no design feels truly adequate. It’s a painful experience for a creative soul—like cutting teeth. But when it’s over, you come away with hard-earned lessons, resilience, and the confidence to tackle new challenges. And hopefully, you’ll never have to work like that again.
