Building Durable Infrastructure Inside an Organization That Won't Hold Still
A design systems practice built from scratch inside a hyper-growth startup — no dedicated PM, high turnover, headcount doubling, and a product growing faster than documentation could follow.
The context
A practice from scratch, inside a company that wouldn't hold still
I joined Calendly in June 2021 to establish a design systems practice from scratch and provide system-level strategy as the company moved from hyper-growth startup into its next stage. When I arrived, Calendly was simultaneously rebranding, launching a new marketing site, and aggressively expanding its enterprise offerings. The company doubled its headcount during my time there. The design org was moving fast, building on patterns that had never been formally consolidated, and it badly needed a shared language.
My job was to build that language — inside a company changing faster than any system could be cleanly documented.
The pivot
When the plan dissolves in the first quarter
I had built an ambitious roadmap anchored on a six-person pilot team — designers and content strategists who would serve as subject matter experts and early adopters. Within that first quarter, four of the six left for new opportunities. The remote work revolution was in full swing, and the talent market was wide open. The pilot team dissolved before it had a chance to function.
The pivot was to stop trying to build a standalone design systems practice and start embedding design systems work inside initiatives that were already well-resourced. Design system goals got aligned to project goals. Decisions that would have gone undocumented got captured in flight.
The name of the game became overlap: finding where the system's needs and the product's needs met, and doing the work there.
56
Components in the library
112
Designers and engineers using it
100%
Product squads adopted in year one
2×
Headcount growth during the engagement
The work
What got built under constraint
- Information architecture auditMapped the existing pattern landscape, identified fragmentation, and established a foundation for component consolidation. Became the reference artifact for the design principles work that followed.
- Design principlesFacilitated sessions with UX designers and content strategists to surface the principles already guiding design decisions — extracted from the team's existing instincts and made explicit enough to teach and to use. Informed onboarding for new hires into a fast-growing org.
- Component libraryA modular component architecture built in close partnership with engineering — flexible building blocks with contribution and governance models that let the system be co-owned rather than siloed.
- WCAG 2.1 AA complianceLed the design work to bring the product into compliance, embedded into the component architecture itself rather than treated as a retrofit. At the time, only 57% of design systems had accessibility guidelines at all. Required organizational work too: helping the team understand accessibility as a shared responsibility rather than a QA task.
- Remote-first working practiceIn a company that doubled headcount during a fully remote period, how the design org worked together was itself a design problem. I ran experiments to establish async-first collaborative rituals using Loom, Miro, Figma, and Slack.
The reflection
The system was the easy part
High turnover, shifting priorities, no dedicated support, a product growing faster than documentation could follow. A system built under ideal conditions wouldn't have been tested the way this one was.
What that looked like in practice: a shared design language that accelerated onboarding as the org doubled in size. Accessibility embedded at the component level, not retrofitted. A modular library that adapted as the product expanded into enterprise. Documentation captured in flight, in context — a living system rather than a static artifact.
Looking back, the collapse of the pilot team was the moment the engagement became honest. Ideal conditions were never coming. Every design system lives inside an organization that is turning over, re-prioritizing, and growing in ways nobody planned for — this one just made that visible early enough to design for it.
The transition from one person's obsession to something a whole team trusts is the hardest part to design — and the most worth designing deliberately.