Senior UX Designer

Curious by nature.
Thorough by choice.

I dig into problems most people walk past. I measure things that haven't been measured. I work until I find the answer — and when I can't get there alone, I find the people who can.

Selected work
Selected Projects

Work that moved
the needle.

Comms with
a point of view.
When to send
What to include
How we write
Who we write for
One voice, many channels
Team alignment
↑ Faster decisions
Principles defined
Full comms coverage
Built with
Entire UX team
Now used for
Collaborator guidance
01
Design Leadership · Team Infrastructure · Communications

Creating Communications Principles for the UX Team

Our team was making communication decisions in silos — when to send a message, what to say, how to write it — with no shared standard. I surveyed and collaborated with the entire UX team to surface how everyone thought about comms, then synthesized that into a set of clear principles covering timing, content, tone, and format. The goal was to speed up decision-making and give the team a shared language to explain our choices to collaborators.

Surveyed the UX team to understand existing mental models around communications decisions
Synthesized responses into guiding principles covering when, what, how, and for whom we communicate
Gave the team a faster way to make and justify communication decisions without repeated debate
Created a shareable reference used when partnering with requesting teams to align on how we work
My Role
Lead + Facilitator
Scope
Full UX team
Impact
Faster team decisions
Preferences Page — Trust Score
81/100
↑ Trackable, category-level signal
Transparency
Control
Reliability
Confidence
Satisfaction
02
Research · Measurement · Preferences Team

Inventing a Way to Measure Trust for Executive Leadership

One of our executive leadership team's key measurements was "trust" — but we had no way to actually measure it. On the Preferences team, I invented a trust measurement system from scratch: a survey embedded in our preferences page that combines targeted questions across several trust categories and calculates a composite score. When any single category dips, we have clean, actionable data to work from.

Identified the gap: leadership had trust as a KPI but zero measurement infrastructure to support it
Designed a survey combining questions across multiple trust categories into a single calculated score
Surfaced on the preferences page to reach users at a moment of high relevance and intent
Category-level breakdown means when trust drops, teams know exactly where to look and what to fix
My Role
Inventor + Lead
Team
Preferences
Impact
Executive KPI
Approver dashboard — multiple runners, multiple stores
Store #4 — Runner: Marcus
AUTHORIZED · $1,840.00 · 10:04:12
APPROVED
Store #7 — Runner: Priya
AWAITING APPROVAL · $3,210.00
PENDING
Store #2 — Runner: Devon
AWAITING APPROVAL · $950.00
QUEUED
SMS sent to approver +1 (•••) ••• 3847
Store #7 checkout pending. Reply YES to approve $3,210 for Priya. Reply NO to decline.
03
Product Design · Checkout · Enterprise Contracting

Enabling Multi-Approver Text Confirmations for Parallel Checkouts

Large contracting businesses operate across multiple store locations at once, with runners checking out at each site simultaneously. The original "text to confirm" system only handled one approval at a time — bottlenecking high-volume operations. I designed a multi-approver flow so approvers can receive, review, and authorize or decline multiple checkouts in parallel, unlocking millions in additional revenue by removing the wait.

Identified the bottleneck: single-thread SMS confirmations were blocking parallel store operations
Designed a system where approvers receive simultaneous texts per runner and can act independently on each
Approvers can authorize all, some, or none of their runners' checkouts from a single device
Unlocked millions in previously blocked revenue by making high-volume contracting transactions faster
My Role
Lead Designer
Users
Enterprise Contractors
Impact
Millions unlocked
AI-augmented design workflow
Figma MCP
Design system connected as live context
→
Faster designs
Consistent, on-system output
Comms Principles
Written to be machine-readable
→
Gemini
Generates on-brand comms + code
Rovo AI · Glean
Org knowledge + people finder
→
Faster answers
Connected across the business
04
AI · Tooling · Ways of Working

Building an AI-Augmented Design Workflow

I've systematically woven AI into how I work — not as a novelty, but as a way to move faster, stay consistent, and spend more time on the problems that actually need a human. This spans tooling, prompting strategy, and org-wide knowledge access.

Connected our design system to Figma via MCP server — components and tokens available as live context during design
Structured our communications principles to be machine-readable, so Gemini can use them to generate new designs
Used Gemini to code new communications end-to-end, grounded in those principles — output that sounds like us, not AI
Integrated Rovo AI and Glean to surface institutional knowledge and find the right people across the org faster
My Role
Builder + Adopter
Tools
Figma, Gemini, Rovo, Glean
Impact
Ongoing
About
Jack Conway

The designer behind the work.

I'm Jack Conway, a Senior UX Designer who gets restless until I understand why something is broken — not just that it is. I'm drawn to complex, journey-wide problems that require digging past the surface before you can design anything worth shipping.

I like to think big, plan carefully, and measure everything. And when a problem is bigger than one person, I find the right people and bring them in.

Journey Mapping
Problem Framing
Measurement & Research
Cross-team Collaboration
Communications Design
Survey Design
Enterprise UX
Facilitation
Stakeholder Alignment
© 2025 Jack Conway · End of portfolio