Barry Maxwell

I design and build technical products, from zero to one.

15+ years simplifying data-dense B2B software, most recently in security. As founding designer at SkyKick, I launched three products and a design system as the company grew to $50M ARR. I shape strategy and ship in Claude Code.

About me

Case Studies

Redesign0→1

Redesigning the migration platform from the ground up

Rebuilt a legacy platform into a modern workflow, cutting support tickets 47% and growing migration projects 53%.

SecurityStrategy

Designing the foundation for security

Moved the Microsoft integration from a marketplace tile to a platform foundation, cutting setup authorizations 75% and seeding a new Defender product.

0→1AI

Designing and shipping a startup MVP in code

Founding designer crafting brand and vision. A coded front end and design system shipped in Claude.

SystemsLeadership

Scaling three products on one design system

From zero to a shared design language across a 70-person engineering org, with 80% of those surveyed reporting hands-on experience.

Working with AI

Start with intent
I set the context, outcome, and constraints to keep AI on task.
Proof the work
Routines and tools I've built check it against the system.
Apply judgment
AI is biased to build. I cut what doesn't earn its place.

Kind words

He leads complex initiatives with clarity and calm, navigating ambiguity with confidence.”

Pete, Director of Engineering

Barry brings clarity, discipline, and craft to complex problems — and creates lasting impact.”

Darren, Product & Platform Executive

Barry isn’t just an exceptional design leader; he’s also the kind of manager, mentor, and colleague you always hope to have on your team.”

Becca, Product Designer · Ex-Amazon

His test-and-learn mindset enabled a collaborative partnership between product marketing and UX, resulting in better user onboarding.”

Jenny, VP Marketing