Tre Stewart as a trail guide holding a lantern

OPEN TO DESIGN LEADERSHIP OPPORTUNITIES

WayfinderTeam builderDesign leader

I help design teams get unstuck. I get closer to the people doing the work and name the decision everyone has been circling.

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Experience

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Field Notes

The trail gets quiet right before things get interesting.

Award markers

FTE Most Innovative Airline Initiative Smart Ramp, Alaska Airlines, 2025.

Webby Award Best Mobile User Interface, Walmart, 2022.

Field note

Tre Stewart Wayfinder

I’ve worked in aviation, retail, identity, telecommunications, media, and the internal tools that keep large organizations moving. The details change. The work often starts in the same place: a team is trying to do good work inside a system that makes the next decision harder than it should be.

The constraint is usually process or trust, or a product that’s collected so many rules nobody can see the actual experience anymore. I help the team find the decision in front of them and give it a next step people can use.

I stay close to the product while we do it. A strategy has to hold up at the screen, in the workflow, and with the people responsible for shipping it.

Current camp Senior Manager, Product Design Alaska Airlines · Oct 2024–Jun 2026

Campfire Tales

EVERY TRAIL LEAVES BEHIND A STORY. Pick a card. I’ll tell you what happened.

Every trail leaves behind a story.

Route 01 / Adoption Deployment
Isn't
Adoption Trail Tre Adventure 01

2025-2026 106 stations Rated L

Deployment Isn't Adoption

RAMP Upload went live across 106 stations. This route follows the work of turning launch into visible, manageable adoption.

+131% Informational scanning across RAMP system

Alaska Airlines

Deployment Isn't Adoption

We replaced RSA Mobile with RAMP Upload across 106 stations. Then we proved launch and adoption are different problems.

The problem

We measured
if we shipped.
Not if it worked.

RSA Mobile was the legacy system of record for ramp upload scanning and load submission. Fragmented workflows, limited visibility for Central Load Planning, and no telemetry — no way to know if agents were using a feature, struggling with it, or working around it entirely.

We launched RAMP Upload in waves. The data showed that deploying devices and installing the app did not guarantee agents were actually using it. These were separate issues, and we lacked the tools to address adoption.

My approach

Instrumentation
as a launch
requirement.

Two moves in parallel. First, I made adoption instrumentation non-negotiable — not a post-launch add-on, but part of what "shipped" means. Pendo gave us daily active users, station-level usage patterns, and where agents were dropping off. Once we could see the gaps, we used in-app guides to deliver workflow guidance in context at the worst-adoption stations.

Second, I established a phased rollout, starting small before scaling to system-wide launch. The legacy platform required weeks for a single fix; RAMP Upload enabled same-day hotfixes. I designed the release process to ensure responsible use of this capability.

At our most challenged stations, the real issue was not resistance to the app but a lack of timely guidance on the new workflow. In-app guides bridged this gap without retraining or manager intervention.

Impact — adoption became visible enough to manage.

From deployed
to adopted.

106

Stations live
across Alaska network

99.49%

Submission success rate
6,394 submissions

7 → 3

Average baggage delay
minutes

Load complications
during network launch

What I'd do differently

Instrumentation
first. Launch
second.

We added adoption tracking after rollout began, which was not ideal. Pendo should have been part of the initial launch criteria, with active user tracking defining "live at a station." When stations made real adoption gains, agents deserved feedback on their impact. We missed a chance to reinforce positive behavior and build trust for future changes.

SITUATION Explore project ↗

Deployment Isn't Adoption cinematic still

Deployment Isn't Adoption mobile preview still

Deployment Isn't Adoption adoption still

Route 02 / People The Goodwill
Bank Trail Tre Adventure 02

2025-2026 Nov 4 to May 1 Rated L

The Goodwill Bank

A designer arrived with a reputation already attached. This route follows the coaching deposits that helped him own the executive room.

Mar 31 Executive presentation led without me taking the floor

Alaska Airlines

The Goodwill Bank

A designer transferred to my team with three flags on his record. By March 31, he was fielding executive process questions on his own.

What I inherited

Not proactive.
Struggles with ambiguity.
Risk-averse.

When he transferred to my cargo team in November, the read from his previous manager was clear: not proactive, struggles with ambiguity, risk-averse. His PM said he'd surface an opportunity and he'd sit on it. When requirements weren't defined, he'd freeze.

I listened. I took notes. Then I set out to form my own view.

What I found was more specific: he came from a team dynamic that had slowly worn down his confidence. The skills were there. He was watching the room, deciding if it was worth using them. Before I could ask him to take more risks, he needed proof that this environment would respond differently.

The sequence that mattered

Make a deposit
before you ask
for behavior.

Six weeks in, before he’d done anything to earn my advocacy, I was in a 1:1 with our director, calling out what product was doing wrong. They’d put him on ULD domain work before he’d been onboarded into the domain, and were wondering why he wasn’t driving. I raised it directly. He found out about that conversation later.

Before I asked for a change, I made a deposit. Coaching does not start with the behavior you want to change. It starts with the environment.

From there: frequent, predictable 1:1s that offered real access, not just check-ins. One concrete target at a time. Supervised field visits to SeaTac cargo ops, then independent ones. When he was meant to own a room, I stepped back and sent coaching notes afterward. Once you take the floor back, there is no clean way to return it in the same meeting.

Where he landed — March 31, senior review

Solo. Senior room.
Trust first.

Jan 21

Led field visit and
presented findings

Mar 31

Answered senior questions
without me leading

May 1

PM validated the shift
to contributing

He presented field observations, process maps, design decisions, error handling, agent testing, and the Q2 roadmap. Senior product and design leaders asked precise process-level questions throughout. Six months earlier, this was a designer who was nervous presenting to his own PM.

What I'd do differently

Name the gap
sooner.

The observation period lasted two months before I named a concrete goal, and that delay had a cost. Product was bypassing him, passivity was setting in, and I was still assessing. Three or four weeks of signal is enough to name a gap and give someone one thing to practice. That timeline cost him. I also did not bring his PM into the coaching loop early enough. She saw the same patterns, and a short conversation in November would have given him consistent signals from two directions at once.

SITUATION Explore project ↗

Route 03 / Systems Identity
Crisis Trail Tre Adventure 03

2021-2024 March 2022 test Rated L

Identity Crisis

Walmart was losing more than $180 million to fraud. This route follows the test that turned identity friction into platform trust.

+10 pts Authentication rate over 20 months

Walmart

Identity Crisis

Phone verification looked like friction until the platform metrics changed the argument.

01 — The problem

$180M in fraud.
Three orgs.
No shared architecture.

Over 100 million users. More than $180 million lost to fraud each year. Only 11 million of a 52 million verified-phone goal reached. Bots were farming accounts to steal Walmart+ trials, and 15% of accounts had undeliverable email addresses. Three product orgs were building identity in parallel silos, with no shared architecture.

Product’s stance: requiring phone verification at sign-up adds friction, reduces accounts, and lowers GMV. The debate stalled, with both sides relying on instinct instead of proof.

02 — My role

Design the
controlled test.

I partnered with product to design a controlled test instead of debating. Mandatory OTP phone verification at account creation versus a no-verification control, rolled out to 50% of web traffic for eight days, then to all users.

The question was never whether friction would hurt conversion. We knew it would. The real question: are the accounts we are losing worth keeping?

I also co-designed the FIDO passkey flow: friction at the gate, smoothness after. Once identity is verified, authentication becomes faster, not harder.

03 — Outcome

Authentication up.
Trust scaled.

+10 pts

Authentication rate
over 20 months

+60%

Verified phone
numbers

+56%

Net GMV per account
$75 → $117 / year

$8.4M

Annualized contribution
profit increase

What I'd do differently

Set the metric
before launch.

A 40% drop in account creation looks catastrophic on a dashboard. It took stakeholder work after the readout to reframe the result. Next time, I would align on the success metric—fewer, higher-quality accounts—before launch, not after. The data was right. The setup for the data was not.

SITUATION Explore project ↗

Trail Markers

Lessons I learned the hard way, collected along the trail.

Marker 01

Momentum is fragile

Teams rarely stop all at once. Momentum disappears through unresolved friction and unclear decisions.

Marker 02

Speed needs alignment

Fast execution means little when teams move in different directions.

Marker 03

Listen for the workarounds

The unofficial process usually reveals where the real problems are.

Marker 04

Deployment isn’t adoption

Launching a system does not guarantee people will change how they work.

Marker 05

Clarity reduces friction

Clear priorities prevent unnecessary organizational drag.

Marker 06

Leadership shows up in ambiguity

Direction matters most when the path forward is unclear.

Echo Ridge

Trail companions

A few words from people I’ve worked beside along the way.

7 references 3 direct managers 4 disciplines

Item 1 of 14

Trust before risk · Walmart

Erin Sian Williams

Sr Director, UX Design · Walmart

Managed Tre directly

Tre is a natural leader and especially shines in helping other designers gain confidence in their role; he helps teammates get comfortable sharing bolder ideas, sharpen their critical skills, and push their work to new places.

Tre Stewart taking a selfie with Alaska Airlines teammates beside an aircraft during field research — **Field context** Getting close to the environment before shaping the product.

Mentorship · American Airlines

Diego Brunot

Manager · American Airlines

Managed Tre directly

Tre has an innate ability to make people feel comfortable and supported, fostering a collaborative and positive work environment. I have seen him reach out to peers during vulnerable moments, providing the mentorship and support needed to help them succeed.

Virtual weekly sync with Tre Stewart and teammates in a video meeting grid — **Weekly sync** Small rituals that keep partnership close.

Strategic craft · Walmart

Demetrios Roumbos

Product Designer · Walmart

Worked on the same team

What sets Tre apart is his remarkable attention to detail paired with strategic vision. He has an uncanny ability to spot subtle inconsistencies while never losing sight of the broader project and problem at hand.

Tre Stewart and a colleague facilitating a hands-on American Airlines workshop with attendees around laptops — **Workshop facilitation** Hands-on guidance while teams make the work real.

Customer focus · Walmart

May Mak

Sr Product Manager · Walmart

Worked on the same team

In our design sessions, Tre is always asking and reminding me, “Why are we doing what we’re doing and what is the benefit to the customer?” His relentless questioning is a testament to his customer-first focus.

Virtual working session with Tre Stewart and teammates in a video meeting grid — **Remote critique** Distributed teams still need a room for the work.

Depth of ownership · Walmart

Michelle Hang Bui

Sr Product Designer · Walmart

Worked with Tre on a partner team

I have never met a designer who is so thorough, involved, and knowledgeable in their focus area to be able to articulate the nitty gritty of every use case to educate others and build incredible experiences.

Team energy The kind of trust that makes critique easier.

Learning through complexity · Walmart

Steph Houle

Sr Manager, Product Design · Walmart

Managed Tre directly

Tre navigated complex problems, like implementing FIDO, by learning through the process and solving for the best user experience possible. Whether it was advanced prototyping or teaching Figma, he was always willing to help.

Baggage office hours video meeting with Tre Stewart and product partners — **Office hours** Open space for product questions before decisions harden.

Resilient leadership · American Airlines

Benjamin Parail

Principal UX Designer

Worked with Tre across two companies

Tre brought a resilient passion to every challenging or complex problem. He advocates for his team by giving them a voice, leading with courage, mentoring young designers, and teaching new skills.

WayfinderTeam builderDesign leader

The trail gets quiet right before things get interesting.

Deployment Isn't Adoption

We measuredif we shipped.Not if it worked.

Instrumentationas a launchrequirement.

From deployedto adopted.

Instrumentationfirst. Launchsecond.

The Goodwill Bank

Not proactive.Struggles with ambiguity.Risk-averse.

Make a depositbefore you askfor behavior.

Solo. Senior room.Trust first.

Name the gapsooner.

Identity Crisis

$180M in fraud.Three orgs.No shared architecture.

Design thecontrolled test.

Authentication up.Trust scaled.

Set the metricbefore launch.

Lessons I learned the hard way, collected along the trail.

Momentum is fragile

Speed needs alignment

Listen for the workarounds

Deployment isn’t adoption

Clarity reduces friction

Leadership shows up in ambiguity

Trail companions

Erin Sian Williams

Diego Brunot

Demetrios Roumbos

May Mak

Michelle Hang Bui

Steph Houle

Benjamin Parail

Want to walk the nexttrail together?

We measured
if we shipped.
Not if it worked.

Instrumentation
as a launch
requirement.

From deployed
to adopted.

Instrumentation
first. Launch
second.

Not proactive.
Struggles with ambiguity.
Risk-averse.

Make a deposit
before you ask
for behavior.

Solo. Senior room.
Trust first.

Name the gap
sooner.

$180M in fraud.
Three orgs.
No shared architecture.

Design the
controlled test.

Authentication up.
Trust scaled.

Set the metric
before launch.

Want to walk the next
trail together?