Moving to GitHub? Lessons from Wayfair's enterprise scale migration
February 28, 2025 // 2 min read
Wayfair’s migration was a masterclass in change management. Through rigorous preparation, developer-first design, and an unwavering commitment to transparency, they not only migrated 15,000 repositories but also paved the way for innovation and cost efficiency.
Published via GitHub Executive Insights
When Wayfair set out to migrate 15,000 repositories from a self-hosted GitHub Enterprise Server to GitHub Cloud, it was clear this wouldn’t be a routine IT exercise. This was a critical infrastructure overhaul touching nearly every corner of the business, from logistics to customer experience. The stakes were high, but the rewards—a more agile development environment, cost savings, and the benefit of advanced features—were more than worth it.
The process revealed critical lessons for leaders driving organizational change. Here's how Wayfair navigated this transformation successfully and what you can learn from their experience.
1. Prepare relentlessly but don’t overdo it 💪
Wayfair started with meticulous preparation.
They prioritized stakeholder engagement and identified key stakeholders early, from repository owners to business units with high churn. This helped ensure that all parties understood the migration’s goals and challenges. They also enacted comprehensive assessments by cataloging not just code but also integrations, workflows, and dependencies to pinpoint potential friction points.
Wayfair also took a phased approach: instead of attempting a risky "big bang" migration, they divided the migration into manageable stages, beginning with low-impact repositories to test the waters.
The takeaway? Preparation is essential. Build flexibility into your plan and prioritize momentum over perfection.
2. Overcome resistance with transparency and trust 🤝🏽
Change often meets resistance, not out of opposition to the goal but from fear of disruption.
Wayfair addressed this by creating robust fallback strategies, ensuring teams felt safe taking calculated risks. They also enacted data-driven transparency with a tracking system that provided visibility into migration progress, fostering trust.
To build confidence in the process, Wayfair celebrated early wins, like successful low-risk repository migrations.
For leaders looking to replicate Wayfair’s success, the lesson is clear: transparency and small, tangible victories can dissolve resistance and build momentum.
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3. Prioritize the developer experience 🌎
The success of the migration hinged on minimizing disruption for Wayfair’s developers.
To accomplish this, automated workflows were essential: the team scripted as much of the migration process as possible, transferring the burden from developers to platform teams. They also created migration guides with real-time updates to ensure that developers always had access to the latest processes and troubleshooting tips.
Importantly, they implemented an “easy button” philosophy where developers could seamlessly transition from one environment to the next with minimal friction, making the change almost invisible.
These efforts highlight the importance of centering the user experience in any transformation effort—ensuring teams can continue working effectively.
4. Focus on high-impact outcomes ⛰️
The migration moved repositories, but it also unlocked new capabilities and benefits.
The cost savings were significant: the migration saved $150,000 annually in hosting costs. By moving to GitHub Cloud, Wayfair also benefitted from GitHub Actions, GitHub Copilot, and advanced security features—tools that would have been costly or impossible to implement on-premises.
Additionally, the migration reallocated resources where teams were freed from managing the self-hosted system, and instead could focus on strategic initiatives like improving CI/CD systems and enhancing security.
These benefits helped Wayfair remain competitive in a fast-paced landscape and arm developers with the tools they needed to boost productivity and drive innovation.
5. Iterate and fail forward ⏩
Wayfair’s phased approach allowed them to test, learn, and adapt at every stage. They embraced a “fail forward” mindset, fixing issues as they arose rather than delaying the migration. This iterative strategy ensured progress without getting bogged down in perfectionism and underscored the value of agility—progress over perfection can drive faster, more impactful outcomes.
If you’re ready to follow in Wayfair’s footsteps, get started with your free GitHub trial today >
Want to learn more about the strategic role of AI and other innovations at GitHub? Explore Executive Insights for more thought leadership on the future of technology and business.
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