I design software where the stakes are high.

Colleen DaileySenior Product Designer
13+ years in design, most recently in legaltech

LinkSquares · AI

Turning an AI Prototype Into a Product Users Could Trust

De-risking a legal AI bet tied to a 5-point GRR goal by making answers easier to reach, verify, and trust.

Role: Senior Product Designer · End-to-end
Scope: 0-to-1 AI question-and-answer experience
Approach: Real customer questions, prototype testing, and AI behavior specs
Outcome: Redesigned direction reached production, March 2026

Read case study

LinkAI answer-first interface: streamed answer, citations, and a stop control

LinkSquares · Design Systems

A system that lets non-designers ship coherent work

Every email was built one at a time, drifting further from the brand and accumulating accessibility risk. There was no system, so I built one: a code-first set of foundations, components, and rules that let product and engineering ship a correct, accessible email without a designer in the loop, and without the product coming apart one email at a time.

Role: Senior Product Designer
Business goal: Let non-designers ship coherent work independently
System: Foundations, components, templates, governance
Outcome: Standard emails became self-serve

Read case study

Reset password

Bear Mattress · E-commerce

Reworking Bear's site for a growing product line

Director of UX at Bear during the company's product expansion. Redesigned the homepage, compare page, and mobile navigation.

Role: Director of UX
Scope: E-commerce · Mobile · Conversion
Projects: Homepage CTA, compare page, navigation IA
Methods: Unmoderated user testing, card sort, VWO heatmaps, A/B testing

Read case study

Bear Mattress compare page with multiple mattresses and feature pills

Independent · Interaction Studies

Designing AI Behavior

A self-directed set of interaction studies exploring how AI communicates the four things users most need to feel: progress, uncertainty, trust, and control. Every tile is live and coded, not a screenshot.

Role: Self-directed exploration
Focus: Progress, uncertainty, trust, control
Format: Live coded bento grid of micro-interactions
Status: Ongoing, added to over time

View the explorations

Teaching and mentoring, on the side

Design Buddies Mentor

I help designers with portfolio and case study reviews (especially framing AI and complex B2B work), interview prep and negotiation, and the messy parts of a design career. Layoffs, imposter syndrome, and career pivots included.

Girl Develop It Instructor

Taught intermediate HTML and CSS, plus design systems fundamentals based on Brad Frost's atomic design principles.

Responses from Colleen’s real work & philosophy