Walgreens

“We believe that honest goods can be sold to honest people by honest methods.” - Charles Walgreen

Walgreens (via Drugstore.com Acquisition)

When Walgreens acquired Drugstore.com, they inherited engineering challenges that required experienced leadership. I was brought in as Director of QA for Performance and Automation.

The Shift in Perspective

I’d held leadership roles before, but those always included hands-on work - leading the team while also writing code alongside them. This was different. At Walgreens, I was explicitly not allowed to write code myself. Pure leadership. Pure delegation.

That forced a shift in how I measured success. My output wasn’t commits or pull requests anymore. It was how well my teams performed, how smoothly information flowed across time zones, and whether the organization was getting stronger or weaker over time. I was there to optimize the communication and productivity between people - the edges between nodes on the company’s social graph.

Learning to fully delegate instead of jumping in yourself is one of the hardest transitions in engineering leadership. Your instincts tell you to fix things directly. The job requires you to build systems and develop people so that problems get solved without you being the bottleneck.

Global Scope

I provided technical and managerial leadership for teams distributed across:

• 2 countries: North America and India
• 3 time zones: PST, CST, and IST
• 2 technology stacks: C#/ASP.NET and Java/JSP on both Windows and Red Hat Enterprise Linux

What I Delivered

Continuous Integration: The organization needed modernization of their build and deployment practices. My job wasn’t to build the CI system myself - it was to champion the initiative, remove obstacles, and ensure my teams had what they needed to deliver it.

Team Development: I established weekly 1:1 mentorship for my directs and advocated for software craftsmanship across the QA organization. Raising the quality bar meant changing how people thought about their work.

Post-Acquisition Stability: Integrations are never easy. Different cultures, different tech stacks, different expectations. I led the team through that transition by focusing on communication, alignment, and enabling automation despite the organizational complexity.

The VP Offer

The engagement started as a contract. Based on the results, Walgreens extended an offer to join permanently as Vice President. I declined because it required relocation.

What This Role Taught Me

Leadership is about multiplication, not addition. One person can only do so much. A leader who develops ten people who each improve by 20% has created far more value than any individual contributor ever could.

Global teams require different leadership. Managing across India and North America means you can’t rely on hallway conversations. You build systems, document decisions, and create processes that work asynchronously.

Pure leadership is a different job. Leading while also coding is one thing. Leading without touching the code yourself is a fundamentally different skill set - and this role is where I learned it.