Checkout 2.0: Revitalizing a Stalled Initiative

May 28

Challenge

In 2021, before a clearly defined Product Development Life Cycle (PDLC) existed at Driveway, an ambitious checkout redesign initiative was pitched and approved upstream. What followed was a textbook example of how projects can lose momentum without proper structure: development began before design was completed, documentation was sparse or nonexistent, and the project passed through multiple teams without clear ownership.

When it finally landed on my desk, stakeholders believed the project was 90% complete. The reality, which emerged only after careful excavation, was closer to 40%. Years of fragmented effort had created a gap between expectations and reality, with tension building between product and engineering teams. What was meant to be an enhancement had become an organizational burden.

Approach

Rather than continuing down the same unstructured path, I recognized that this project needed reimagining, not just resumption. I approached the situation with three priorities:

Truth-seeking: Creating a shared understanding of the project's actual state
Scope refinement: Identifying the essential core that would deliver value quickly
Cross-functional healing: Rebuilding trust between teams that had grown frustrated

I worked closely with product leadership to carefully analyze the original scope, identifying elements that could be converted to future enhancements. Simultaneously, I simplified overly complex navigational components, reducing technical scope without compromising the core user experience.

Recognizing that documentation—or lack thereof—was at the heart of the tension, I advocated for a fresh start: creating a new epic with clear documentation rather than trying to resurrect fragmentary records.

Process Highlights

Creating Common Ground: Seeing the frustration between product teams (who believed engineering could simply execute) and engineering teams (who felt they lacked sufficient documentation to proceed), I proposed a solution that acknowledged both perspectives. We assembled a cross-functional team with key members from each discipline to create a Solution Requirements Document that would serve as our shared understanding.

Design as Documentation: To break the impasse, my design colleague and I created comprehensive design specifications for the entire checkout flow. These specifications became the authoritative reference point for both engineering implementation and QA validation, replacing years of scattered documentation with a single source of truth.

Strategic Simplification: I made the difficult but necessary decision to reduce design complexity and cut features to create a manageable scope. Rather than presenting these as compromises, I framed them as strategic choices that prioritized delivering value to users sooner—preserving the essence of the initiative while making its completion feasible.

Outcomes

What had been projected to take another nine months was delivered significantly sooner, delighting stakeholders who had begun to view the project as a perpetual work-in-progress. The success manifested in several ways:

A streamlined checkout flow that maintained core functionality while eliminating unnecessary complexity
Renewed trust between product and engineering teams, who developed a model for collaboration on future initiatives
Comprehensive documentation that not only served this project but established standards for future work
A significant reduction in technical debt by resolving long-standing design and development inconsistencies

Perhaps most importantly, the project transformed from a source of organizational friction into a case study in effective cross-functional problem solving.

Reflection

This experience reinforced my belief that design leadership is as much about creating clarity as it is about creating interfaces. By recognizing that the project's challenges were organizational rather than purely technical or aesthetic, I was able to apply design thinking beyond screens—to teams, processes, and expectations.

Sometimes the most valuable design work happens not in adding complexity but in revealing simplicity that was hidden all along. The success of this project wasn't just in what we delivered, but in how we transformed a pattern of fragmentation into a cohesive path forward.