Year two at Gap. A 15-person monitoring platform team had been charged with migrating observability from open source tools — Grafana, Nagios, Prometheus — to New Relic and Splunk before PEAK weekend. 130+ ecommerce teams depended on it for visibility into the highest-stakes event of the retail year.
The team was at a complete standstill. The Architect and Lead Developer were in open conflict and nothing was moving. The Director had tried and failed to break the deadlock.
He brought me in after watching what I’d done with the infrastructure teams the year before.
This wasn’t a morale problem or a leadership vacuum. It was two technically strong people who had decided they couldn’t work together, and a team that had organized itself around their conflict instead of the mission.
130+ ecommerce teams were waiting. PEAK was coming. The Director was out of moves.
Weekly 1:1s with every team member clarified the real issue: the team wasn’t the problem, the conditions were. The conflict between the two leaders had become the center of gravity. Everything else — the work, the deadline, the downstream teams depending on them — had become secondary.
I shifted the center of gravity. I created a shared mission: the 130+ ecommerce teams are our customer. Not an abstract org goal — a specific, named group of people depending on us to deliver.
Then I made that commitment public. I ran training sessions at both Gap HQ and Pleasanton and personally worked with all 130+ ecommerce teams to ensure attendance and buy-in. Once those teams were engaged and expecting delivery, non-delivery became socially and operationally unacceptable. The leaders’ disagreement didn’t disappear — it just became harder to sustain than the work in front of them. They found enough common ground to start building again.
PEAK weekend observability ran 100% on the new platforms.
The CTO and CIO had full dashboard visibility across the entire event — something that had never existed at Gap before. All 130+ ecommerce teams — plus the DevOps infrastructure teams — had live dashboards to catch issues before they became incidents. Zero loss of visibility during the cutover.
My last day was the Tuesday after Cyber Monday.
“I was very fortunate to have Seemant as my first product hire who spanned across four distinct spaces — cloud infra, application infra, build & deploy tooling, and telemetry. Seemant was trusted by his teams as well as stakeholders to lead the org in an entirely new product direction that culminated in empowering dev teams to operate much more independently and delivering solutions that significantly improved dev velocity. I genuinely miss working with Seemant, and would work with him again in a heartbeat.”
Kartik Garg · Head of Product & Tech, AI Studios — Amazon