I've spent 15+ years leading design at Alaska Airlines, Walmart, and American Airlines — building the teams and operating models that solve the problem behind the problem, at the scale of 18 million bags a year and 52 million users.
Most design problems arrive with a diagnosis already attached — training issue, interface problem, adoption gap. My first move is to treat that diagnosis as a hypothesis, not a fact.
At Alaska Airlines, baggage scanning rates were underperforming. The org had already landed on an answer: training. Before we built anything, we asked a different question — what are the actual conditions our users are operating in? That question led to the tarmac. January. Gloves. Twenty minutes to turn an aircraft.
We investigated. We reframed. We aligned the team and the stakeholders around what the evidence showed — not what the brief said. Scanning went up 131%. That's the approach. Questions before answers. Shared understanding before solutions. The work is better when everyone is solving the same problem.
Diagnose the systemic problem, not the surface one. Ask the question the room isn't asking yet.
Operating models, governance, and rituals the team can run without me in the room.
Decisions that compound. Rituals that outlast any single leader. Work that still matters in two years.
Careers over deliverables. 0 attrition in 18 months. PIP to promotion-track. The team I build is the work that matters most.
Each started with a systemic problem no one had the operating model to solve. Framed as leadership challenges, not industry case studies.
500+ component variants, a merger in motion, and no Director. I built the contribution model, quality gates, and ownership structure that gave Jetstream 2.0 a spine — and cut handoff friction by 50%.
Three teams. Conflicting KPIs. Auth failing at 60%. I didn't redesign the flows — I realigned the org around a shared model and scaled verified users from 11M to 52M.
COVID hit. The team went from 3 to 1. The cloud deadline didn't move. I consolidated 579 screens to 119 and shipped 8× faster — without dropping the bar.
The team wasn't hitting its mark. I introduced ESAT as an alignment mechanism, launched peer review and office hours, and shifted the org to 3-in-the-box pod working. The measurement system was adopted org-wide.
Games, agencies, television, airlines, retail. Different terrain; same throughline — build systems that let teams move faster under chaos.
Cut design-to-handoff from 3 weeks to 48 hours. Early people leadership. High-visibility launches: Taylor Swift Now, Election 2020.
3 weeks → 48 hrs handoff · 45% efficiency gain
Field observation revealed a decision problem, not an interface problem. 579 → 119 screens. 8× faster deployment. Touchless check-in shipped during COVID.
579 → 119 screens · +47% prepaid bag adoption
One sign-in for 80M+ users. Scaled verified phones from 11M to 52M. Surfaced an $864M GMV opportunity. -38% auth errors. +30% login success.
$864M GMV opportunity · 52M verified users
23-person org, no Director, merger in motion. Built the operating model. Launched Jetstream 2.0. 0 attrition in 18 months. 131% scanning increase.
131% scanning increase · 18M scans/year
The short list. Each one has a longer story — ask, and I'll tell you about the time it mattered.
Design leadership starts with understanding the conditions people are working in — not evaluating their output. Trust, clarity, and psychological safety aren't soft outcomes — they're the operating conditions that make everything else possible.
Structure creates freedom. Clear intake, governance, and decision rights mean teams spend less time defending their work and more time doing it. The absence of process doesn't make teams faster — it makes them fragile.
Every design decision is a business decision. My job is to connect the work to the outcomes that matter at the org level — and to frame design not as a service function but as a mechanism for reducing risk and unlocking growth.
The problem that arrives is rarely the real problem. Most delivery failures, team breakdowns, and missed metrics are symptoms of something upstream. I work at the constraint level — because that's the only place where solutions actually scale.
I'm open to Sr. Manager and Director of Product Design roles. If you're building something that needs a leader who investigates before building — and who builds the operating model that makes great work repeatable — I'd love to talk.
Or email directly: iamtrestewart@gmail.com