Design Executive & Systems Thinker

I find clarity in complexity and turn it into impact.

Design executive and systems thinker with 20 years building teams, products, and the organizations that sustain them.

Currently at Heggerty
Maine / Remote
Portrait of Daniel Filson

What people say

“It's so rare to have such a blend of strategic thinking and creative talent. I would 10/10 hire him again, if given a chance.”

Heather Wiederstein CPO · Hiring Manager

“Dan is hands-down the most caring and effective manager I've had. He's strategic yet humble, focused but attentive, and excellent at turning high-level concepts into actionable items.”

Cindy Tsai VP of Product & Experience Design · Direct Report

“There are a lot of things I admire about Dan: how he sizes work against iterative quick wins while directing his team toward a lighthouse; how he champions content as integral to UX; how he consistently defuses tension by making everybody laugh.”

Amanda Morrison VP of Content Design · Cross-Functional Partner

“Daniel is one of those individuals everyone should have the opportunity to work with during their career. His personality, passion, strategic thinking, and creativity touch everything and everyone around him.”

Brent Hartsell Senior Director · Cross-Functional Partner

“Daniel changed the way I think about accessibility for the better, stressing the benefits of universal design and continuously demonstrating that tweaks to our UX and UI could make our product better for everyone.”

Laura Bridgewater Senior PM · Cross-Functional Partner

“Dan is, hands down, one of the best managers, design strategists, team builders, and collaborators I've ever worked with. As a design thinker and strategist he is laser sharp in his insights, methodical in his use of data and research, and collaborative in his decision making.”

Carina Reeves Principal Product Designer · Direct Report

Impact at a glance

70%

AI-driven operational efficiency gain

$3.1M

Annual revenue increase from a single program

1.5%

Reduction in customer contacts

30%

Usability improvement from platform redesign

300+

Practitioners trained on original frameworks

What makes this different

Design leadership across 6+ industries

Not a specialist. A pattern-matcher.

Accessibility rooted in lived experience

Dyslexic designer. WCAG consultant. Inclusive design educator.

AI-fluent practitioner and teacher

Building AI tooling and teaching AI-driven design workflows.

Shaping the next generation

Adjunct Professor of UX Design, Husson University.

Selected Work

Executive oversight on critical infrastructure and consumer platforms.

AI content workflow showing script processing, format review, auto extraction, and upload steps
EDTECH / AI

Replacing four contractors with one AI-powered workflow

Directed the development of an AI content ingestion tool that eliminated the need for a manual contractor team, cutting curriculum processing time by 70%.

View Case Study — Replacing four contractors with one AI-powered workflow
Mobile insurance app screens showing policy management, claims, and roadside assistance features
INSURANCE

2.5 stars to 4.7 in a regulated industry

Directed the redesign of a customer insurance app across policy management, claims, and roadside assistance. Received the company’s highest individual honor.

View Case Study — 2.5 stars to 4.7 in a regulated industry
Person using augmented reality on a phone to measure and plan a room layout
MARKETPLACE

27% fewer project failures through AR innovation

Identified the root cause of onboarding friction in a design services marketplace and led the team from discovery to an AR floor plan tool.

View Case Study — 27% fewer project failures through AR innovation
Team collaborating at a whiteboard covered in sticky notes and process diagrams
ORG DESIGN

One framework, 80+ practitioners, zero resistance

Built a Career Development Framework and Competency Model using a user-centered approach. The team helped build it, so the team adopted it.

View Case Study — One framework, 80+ practitioners, zero resistance
Classroom setting with a laptop displaying a professional learning platform
EDTECH

From zero to award-winning product in under a year

Led discovery, strategy, and design that created a new product line, stood up a dedicated team, and won national recognition.

View Case Study — From zero to award-winning product in under a year
Woman holding a cable-knit sweater on a hanger, evaluating fit and sizing
COMMERCE / RETAIL

Size & Fit program increased revenue by $3.2m while reducing customer contacts by 1.5%

Directed the approach, research, design and roadmapping; Led 10 person cross departmental team; Drove the evangelization of the strategy

View Case Study — Size & Fit program increased revenue by $3.2m while reducing customer contacts by 1.5%

How I Work

Build the RIGHT thing

Strategy and discovery. I translate ambiguity into structured opportunity. Before a team solves a problem well, someone needs to make sure they’re solving the right one. I stand up research operations, build insight pipelines that connect directly to executive roadmaps, and create the conditions where strategy is evidence-driven rather than opinion-driven.

Build things RIGHT

Execution and craft at scale. I set the quality bar and build the systems that maintain it. Accessibility and inclusivity are embedded from the start, not bolted on at the end. Design systems, governance frameworks, and operational rigor that let teams ship with confidence and consistency.

Build the team that drives outcomes

The most leveraged thing a design leader can do is build an organization that produces great work without depending on any single person. Including the leader. I design the career frameworks, competency models, and coaching rhythms that make that possible.

About

Growing up dyslexic gave me firsthand experience with what happens when systems aren’t built for everyone. That’s not a footnote in my career. It’s the throughline.

It’s why accessibility isn’t a compliance checkbox for me. It’s a design principle. It’s why I build frameworks and systems rather than one-off solutions, because the right structure helps everyone, not just the people it was designed for.

That same instinct shapes how I lead teams. Everyone wants to do well. A clear mission, transparency, opportunity, and the right tools will help them get there. That philosophy shows up in the competency models I build, the research operations I scale, and the way my former reports describe working with me.

It also drives me to teach. At Husson University, I teach the next generation of designers that accessibility and systems thinking aren’t advanced topics to learn later. They’re foundational.

Based in Cumberland, Maine. Dad of two. I build furniture when I’m not building design systems. Cook Chinese-inspired food. Have a karaoke habit I’m not apologizing for.

Chairman’s Award for Excellence, Travelers, 2022

Daniel cooking, singing karaoke, and building furniture

Career arc

Twenty years. Six industries. One throughline.

Wayfair EY (Ernst & Young) EF Education First Heggerty Learning Ally Dirigo Interactive Travelers L.L.Bean Husson University EMC Digital Investing.com

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