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Kyle Dickson

@kyledickson

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I build and lead UX teams that improve products at scale.

United States

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I've led UX and product design teams at Shopify, NICE CXone, Hudl, and Xactware, building teams, design systems, and research practices that improve software at scale.

At Shopify, I grew the Support design team from 2 to 8 designers serving 5M+ merchants. Our workflow redesigns improved advisor efficiency 35%, increased first-contact resolution 32%, cut handle time 22%, and reduced new-advisor onboarding from six weeks to three.

I've built a 100+ component design system adopted by eight product teams, led AI-assisted product experiences, and ship production software daily through my consulting practice using Claude and Claude Code. I ground product decisions in field research, accessibility, and working prototypes rather than static comps.

Experience

Work history, roles, and key accomplishments

Current

Founder

Current

Two22

Jan 2016 - Present (10 years 8 months)

UX and product consulting alongside in-house roles; currently shipping production software daily with AI-assisted development as working-prototype design practice.

UX Consulting Product Design AI assisted Development Prototyping

Sr. Product Designer

GameChanger

Apr 2025 - Nov 2025 (7 months)

Designed LLM-powered coaching insights for a consumer sports platform serving 750K teams, defining patterns for AI recommendations and confidence framing.

Product Design AI LLM Prototyping User Research

UX Design Manager

Shopify

Apr 2022 - Nov 2024 (2 years 7 months)

Led product design for the Support organization serving 5M+ merchants; built and coached the team from 2 to 8 designers. Defined AI-assisted support experience principles, drove self-resolution up 10%, and improved advisor efficiency by 35%.

Design Leadership Team Building UX Strategy User Research AI assisted Design Accessibility Cross Functional Collaboration Executive Communication

UX Design Manager

NICE CXone

Mar 2019 - Apr 2022 (3 years 1 month)

Led UX for CCaaS products serving 1M+ agents across 25,000+ organizations. Built and owned a design system of 100+ components adopted by 8 product teams, cutting design-to-development cycle time by 40%.

Design Systems Accessibility Inclusive Design User Research Usability Testing Product Strategy Leadership

Product Designer

Hudl

Oct 2015 - Feb 2019 (3 years 4 months)

Took the volleyball product from concept to product-market fit with 400,000+ users and $3.5M+ ARR. Redesigned the football product for 16,000+ teams, cutting support calls by 70%.

Product Design User Research UX Strategy Cross Functional Collaboration

UX Design Manager

Xactware (Verisk)

Mar 2014 - Oct 2015 (1 year 7 months)

First design leader in the company; built the practice from 1 to 5 designers and established research and design review rituals. Shipped the company's first mobile claims app for top-100 P&C carriers.

Design Leadership Team Building User Research Mobile Design Insurance