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You probably have a hard design problem. Yeah, I can fix those.

Clinical workflows. AI products. Teams that needed to grow up fast. If your product is hard to build or hard to use, or both — that's where I do my best work.

Services

Four ways in.

Fractional Head of Design

You have designers. You don't have design leadership. I step in: direction, team mentorship, research practice. 2–3 days a week. Not just producing work — shaping it. The right call at Series A–C before there's a full-time design leader in the seat.

Ongoing retainer

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Design Org Build

Designers exist. The function doesn't. I build the infrastructure: process, principles, career frameworks, research practice. You walk away with a system that works without me. For teams scaling design for the first time, or ones that built it ad hoc and are starting to hit the ceiling.

60–90 day project

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AI Product Design Sprint

You're building an AI feature. I've shipped them in production. I design how those interactions work: where AI is invisible, where humans step in. You walk away with a clickable prototype ready for customers and investor demos. Right call before you commit to the full build — interaction design is where most AI features go wrong.

4–6 week project

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Proof

  • Twenty years of product design. Ten in leadership. Healthcare, SaaS, startup, enterprise.

    TripAdvisor, edX, Carbonite, HealthEdge. The users were never similar. The work always started the same way: listen until they trust you enough to tell you what's actually wrong.

  • Zero voluntary attrition. International team. 5+ years.

    Across 5 years and two company acquisitions. Nobody left voluntarily. Zero exit interviews.

  • First-gen AI. Summarizers, agentic agents. Shipped in clinical workflows.

    2024. Production, not a demo. 10 minutes per interaction = millions in recovered staffing spend.

  • 0→1 to $100M ARR. Every stage.

    Series A startup to $100M ARR healthcare platform. The problems look different at each stage. The fundamentals don't.

  • NPS 68. Conversion up 36%. Six months of testing to earn those numbers.

    Renoviso, 2018. Tools built from scratch. The conversion tests ran six months to earn that number.

  • 100+ hours of clinical ride-along research. Built the program.

    I sat with care managers while they worked. 10+ health plans. 25 participants. Findings changed what we built. Million-dollar contract renewals followed.

About

Andy Waldrop at Gillette Stadium, 2025.

Gillette Stadium, 2025. France vs. Brazil.

Hi! I'm Andy, no not the one with the beer in the background, front and center. My wife calls this divorced-dad-at-a-soccer-game. I guess I'm at the stage where middle aged men take selfies like this, marriage status be damned.

This was France vs. Brazil before the World Cup at Gillette, outside Boston, MA. I went with my family, despite their absence from my photo. I have a wonderful wife, two sons, couple cats, dog, house… It took me a while to get here though; I've been a professional cook, waiter, financial service rep, car salesman, and comedian all before I took the leap to experience and product design. Every job was the same problem in a different room. If they don't trust you, you're not listening.

I make a living in those rooms. Not a design silo. I'm in product conversations, engineering trade-offs, leadership decisions that shape the roadmap. Design doesn't work in isolation; it works when it's in every room that matters. I speak product. I speak design. No translation required.

20+ years of product design. 10+ years of leadership. Healthcare technology, first-generation AI products, 0-to-1 startups, $100M ARR enterprises. Common thread throughout it all: the person on the other end of the screen.

Most recently, Director of Product Design at HealthEdge for six years. Built an international team that stayed. Zero voluntary attrition across two acquisitions. Shipped AI summarizers and agentic agents into clinical workflows before the craze of 2024. Production, not demos. Research infrastructure from scratch. Clinical ride-alongs. A 1,500-person testing panel. Not because anyone asked; because the decisions are better when we know what's true.

Before that: Renoviso, edX, Carbonite, TripAdvisor, agencies. Oblivious to the fact that it would all culminate in a divorced-dad selfie at a soccer pitch.

Let's talk.

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