Wayfair Customer Experience:

Leading a $100M Digital Transformation

Image of web and app product detail page — One of hundreds of screens replatformed across Web and native App.

“This was the highest-priority initiative in the company. We built the foundation for Wayfair’s future.”

Project Summary

Wayfair needed to replatform its entire customer journey experience across five brands and four international markets. This affected billions in revenue and traffic. When I joined, only 22 percent of journeys had started migration, goals were unmet, and coordination was breaking down.

My Role:
As Senior Technical CX Program Manager, I led the program across Web and App from strategy through delivery. I coordinated 35+ teams and 200+ contributors, implemented the program structure, visualized progress, managed risk, and introduced GenAI-powered reporting.

The Challenge

Release Phases — Custom diagrams like this phased release plan ensured alignment across domains.

The program had major gaps:

22% adoption rate, far below expectations
0% goal achievement in the prior cycle
Unclear dependencies and delivery risks
35+ teams working without unified coordination
No shared progress visibility for leadership
Misaligned stakeholder priorities

Failure would have compromised the platform foundation for customer experience at Wayfair. My goal was to stabilize, realign, and deliver.

Discovery and Frameworks

Image of a whiteboard — Whiteboard from team session to align on a path forward for program-level delivery optimization

Dependency Mapping

JIRA MVP Progress — Mapping dependencies across customer journeys and cross-functional teams.

Diagram of dependencies mapping — Visual showing planned agile work rolling up to OKRs.

Mapped 100+ dependencies across all domains
Created shared taxonomy and impact scoring
Prioritized critical paths and unblock sequencing

Accountability Structure

Implemented a RACI model
Defined escalation and resolution paths
Created aligned communication and reporting loops

Visibility and Alignment

Progress Visualization

OKRs progress slide — Visualized progress against OKRs and milestones.

Image explaining RAID log — Example risk management RAID log used during the weekly, 35+ person Scrums of Scrums that I led.

Dashboarded live adoption, risk, and team progress
Built milestone timelines and cycle targets
Improved transparency for VPs and Directors

Roadmap Realignment

Roadmap planning — Rebuilt roadmap structure to reflect delivery logic and priorities.

Jira Roadmaps — Example Jira Advanced Roadmap showing scope aligned to KR outcomes. There were ~20 KR outcomes per planning cycle.

Broke down delivery into high-impact increments
Aligned roadmap with dependency maps and OKRs
Phased rollout by journey and platform readiness

AI-Powered Reporting

OKRs Tool — GenAI-powered tool that connected Jira to strategic outcomes.

I built Wayfair’s first GenAI program reporting system:

Synced OKRs with real-time Jira data
Flagged risks before blockers emerged
Created weekly insights for leadership review
Automated user story generation for clarity

Execution and Launch

Milestone tracker used across teams to track cycle delivery.

Delivered real adoption increases in three consecutive quarters
Focused teams using incremental milestone plans
Balanced feature development and platform migration

The Solution

The coordinated strategy I implemented resulted in:

A “one team” delivery approach across 35+ groups
Transparent dependency tracking and issue escalation
Centralized progress visualization for leadership
AI-enhanced reporting and user story generation
Strategic prioritization based on revenue and readiness

Scope doc — Scope templates standardized planning and ensured consistency.

Image of release checklist — Release checklist template I created to ensure all dependencies were accounted for and stakeholders have signed off on the launch.

Team at launch — Cross-functional launch team working on go-live day.

Health metrics dashboard — Monitored platform performance to mitigate launch risk.

Outcomes

Cycle success slide — Cycle completion stats from executive reporting deck.

72% adoption (up from 22%)

100% of goals achieved 3 cycles in a row

Platform drove $68M+ in new revenue

Feature launches were 40% faster

Improved team morale and lower burnout

Stronger cross-functional collaboration

Lessons Learned

Visibility drives velocity
Transparent progress tracking unlocks productivity
Empathy enables leadership
Understanding constraints makes change sustainable
Structure supports creativity
A shared framework frees teams to do great work
AI unlocks insight at scale
GenAI reporting changed the speed and quality of decision-making
Integration is harder than implementation
Culture and coordination take more effort than code