Barry Maxwell — Resume

15+ years designing complex B2B SaaS products for technical audiences — including security, compliance, and data protection. I operate independently in ambiguous spaces, work AI-first from strategy through execution, and build systems that hold up at scale. Grounded in both visual design and front-end development.

Work Experience

ConnectWise – Principal Product Designer

Seattle, WA · Remote, 09/2024 – 02/2026

Designed and shipped the SaaS Security MVP in 9 months — providing IT professionals with security monitoring and automated compliance reporting across customer Microsoft 365 tenants.
Led the Microsoft Partner Center integration with AI-assisted multi-tenant mapping — drove cross-team alignment, shipped on schedule, and established a platform pattern referenced by other product teams.
Replaced static documentation with a conversational AI interface designed for partners managing security without a dedicated specialist.
Rebuilt the Figma Table component (78% fewer layers, adopted across 20+ designers) and established a component defect process that standardized quality across the design org.

SkyKick – Product Design Director / Creative Director

Seattle, WA, 10/2015 – 09/2024

Founding designer at SkyKick — designed the brand from the ground up, led UX across all three products from 0→1, and contributed to $50M ARR, 3.5M+ active end-user licenses, and $200M+ in capital raised.
Oversaw Cloud Backup redesign — Microsoft 365 data protection and recovery for IT partners' customers. Grew to 200,000+ active orders across 5,400 partners. 86% gross / 108% net retention.
Defined the product vision for Cloud Security and designed core features — automated security compliance reporting and remediation for IT partners' customers.
Built a cross-product design system unifying 3 IT service products; established a UX research practice including hiring, tooling, and running internal studies.
Redesigned Cloud Migration, reducing support tickets by 47% and increasing migration projects by 53%.

Swivel Studio – Design Director

Seattle, WA, 09/2003 – 10/2015

Founded and ran Swivel Studio for 12 years — delivering brand identity and digital experiences for tech startups, architecture firms, and boutique clients across design and front-end development.

Cole & Weber – Art Director

Seattle, WA, 01/2000 – 02/2003

Directed digital branding and advertising campaigns for Nike, K2, and Texas Instruments.