Lessons from a Decade of Design Systems
Design systems are more than a collection of design files—they are living, evolving entities that shape the user experience and operational efficiency of organizations. Over the last decade, I’ve designed, coded, maintained, and managed the development and creation of multiple design systems, learning invaluable lessons along the way.
Here are my top insights:
Have a good plan.
At Pie Insurance, I designed, launched, and championed the creation of Pie’s design system, cleverly known as Pie-brary. What started as a pet project to make design spec creation faster and more consistent, quickly morphed into a 4 year long project of peaks and valleys.
- It’s a marathon, not a sprint. While design files can be created in weeks, the real work—development, infrastructure, implementation, and training—requires years, not months. Even with a dedicated team, long-term planning is essential, and ongoing maintenance demands a dedicated individual or team to ensure the system evolves with organizational needs.
- Collaboration is key. A successful design system transcends design files—it’s a shared framework requiring unified input. Engineers bring architectural foresight, product managers allocate roadmap time, and marketing ensures alignment with brand standards in colors, fonts, and components. Engaging cross-departmental teams early is essential to avoid downstream setbacks and ensure the project stays on track.
- Plan for implementation. Pie-brary’s biggest setback occurred during implementation when the engineering team responsible for building the system worked in isolation. The result? A system that didn’t align with existing applications, forcing extensive refactoring and delaying ROI gains. A cohesive implementation plan ensures seamless integration, preventing costly setbacks and keeping the project on track.
Accessibility is deeper than you realize.
At Open Technology Solutions, I was responsible for WCAG remediation across a consortium of three credit unions, working with third-party experts and an off-shore development team to identify, triage, and implement targeted accessibility changes to meet WCAG Level AA standards. Over the course of six months, we improved the consortium’s accessibility score by 10%. This experience underscored the challenges of adapting legacy frameworks and the importance of integrating accessibility best practices from the start to avoid costly and complex retrofitting efforts.
- More than just color contrast. While designers focus on meeting WCAG standards for color contrast and target sizes, developers must address deeper complexities. Effective components require proper heading hierarchies, ARIA labels, and semantic form structures. However, the real impact lies in intuitive keyboard navigation, seamless screen reader integration, relative units of measurement (ems and rems), and meaningful alt text for images and videos. Neglecting these essentials during component creation leads to costly and time-consuming remediation later.
- Leverage expertise. Accessibility is a nuanced and ever-evolving discipline. At Open Technology Solutions, we partnered with Level Access to conduct comprehensive audits, identify areas of non-compliance, and deliver prioritized remediation plans. Beyond guidance, their resources included extensive documentation, industry-recognized certifications, and a robust system of record, providing not only a roadmap for improvement but also legal protection against potential lawsuits. This partnership reinforced the value of expert support in building accessible and defensible digital experiences.
Transitioning design tools is a strategic undertaking.
The design landscape evolves rapidly—Photoshop, Sketch, XD, Figma—but chasing every new tool isn’t sustainable. At Pie Insurance, we made the deliberate shift from XD to Figma only when the business case clearly outweighed the operational costs. What seemed like a straightforward transition revealed itself to be a complex initiative, ultimately demanding a dedicated Design Ops role for 9 months to ensure its success.
- Business Case > Fad. Switching tools for every trend isn’t sustainable. When Figma began gaining traction, half the team pushed for migration, but as head of Product Design, I prioritized practicality over hype. Our existing tool met our needs, and I couldn’t justify the transition—a decision that, unfortunately, led to the departure of a talented team member. But over time, Figma’s capabilities, industry adoption, and Adobe’s sunsetting of XD features made the transition a strategic choice rather than a reaction to hype.
- Dedicated Design Ops: The Key to Seamless Transitions. Regardless of team interest, change is hard. For Pie’s move from XD to Figma, a Design Ops lead was essential in coordinating trainings, hosting weekly feedback sessions, and maintaining clear communication. This role ensured the team was aligned, timelines were met, and a definitive cutover date was enforced, minimizing overlap costs and driving a smooth, efficient migration.
The bottom line...
Design systems are long-term initiatives that require commitment, collaboration, and resilience. They demand buy-in from leadership, cross-departmental teamwork, and a willingness to endure challenges. While the return on investment isn’t immediate, it compounds over time through reduced development costs, consistent user experiences, and a cohesive brand identity.
By embracing these principles, organizations can create design systems that not only endure but drive meaningful impact across the business.