My Driveway: Orchestrating Digital Transformation at Scale
Challenge
Lithia Motors, with its network of over 300 dealerships across the country, envisioned Driveway.com as the cornerstone of an automotive ecosystem where users could seamlessly buy, sell, and manage their vehicles in one unified space. The ambition was substantial: expand the My Driveway platform to include over 380 vehicle management features—from recall notifications and service scheduling to equity monitoring and valuation tracking—all while maintaining design excellence and user-centered experiences.
This wasn't merely a design challenge but a leadership one: how to orchestrate multiple teams, maintain quality standards across a vast feature set, and deliver at a pace that would meet aggressive business timelines.
Approach
When the business engaged an agency for this massive initiative—bringing in a team of upwards of 90 people including 13 agency designers—I embraced the opportunity to demonstrate the power of thoughtful design leadership at scale.
As the design leader, I provided both project management and design guidance for every feature released. Rather than simply delegating tasks, I created a structured mentorship system, helping agency designers understand our design rigor expectations and how to effectively leverage our design system. I focused on:
Strategic oversight: Managing timelines and deliverables across all 13 designers while ensuring quality never suffered for speed
Design mentorship: Elevating the agency designers' work through systematic guidance and feedback loops
System integration: Teaching the value of our design system as both an efficiency tool and quality assurance mechanism
Cross-functional alignment: Establishing clear communication channels between agency designers and internal stakeholders
My approach treated the agency designers not as separate entities but as extensions of our design vision—temporary members of our constellation who needed the right guidance to shine within our ecosystem.
Process Highlights
Design Crit Intensification: I instituted thrice-weekly design critiques with the entire team—internal and agency alike—transforming what could have been disconnected workstreams into a cohesive design community. These sessions became the heartbeat of our process, a place where solutions were refined collectively and where our design language evolved to meet new challenges.
Design System as Common Language: Recognizing the potential for inconsistency with multiple teams working in parallel, I incorporated our Design System lead into critical meetings and personally trained engineering teams on how to recognize design system components in specifications. This became our Rosetta Stone, allowing disparate teams to communicate through a shared visual vocabulary.
Strategic Design Lead Time: Perhaps most critically, I orchestrated our design workflow to stay months ahead of development. This foresight created a strategic buffer that allowed product and stakeholders to make nimble adjustments when engineering teams showed varying velocities—allocating larger features to high-performing teams and right-sizing deliverables for teams that needed more support.
Outcomes
The initiative successfully delivered the full feature set, transforming Driveway.com from a transactional platform to a comprehensive vehicle management ecosystem. Beyond the tangible deliverables, we achieved:
Seamless integration between internal and agency resources, creating a scalable model for future initiatives
Stakeholder flexibility through design-led planning, allowing for real-time adjustments to maximize engineering throughput
Enhanced user experience validated through both usertesting.com research and Amplitude metrics
A strengthened design system that evolved to accommodate new use cases while maintaining coherence
Surprising and successful user engagement metrics that delighted business stakeholders
Such impressive results that in 2025, the business extended our management model, asking all other technology teams to adopt our processes for agency engagements
Reflection
This project reinforced my belief that design leadership at scale isn't about controlling every pixel, but about creating the conditions where quality can emerge naturally from well-structured teams. The design lead time we established wasn't just a buffer against uncertainty—it was a manifestation of design thinking as a strategic business resource, allowing the entire organization to become more responsive and adaptive.
In the end, what appeared on the surface as a challenge of feature quantity became an opportunity to deepen our design quality, proving that with the right leadership approach, scale and craft can grow together rather than compete.
