Product and engineering leader who still builds. Twenty years of shipping software, from writing the first lines of a startup to leading product at Square. Built and scaled teams across point of sale, vertical software, platform, and AI. CTO of BookFresh, acquired by Square in 2014. Ships side projects in the open because building is the point.
Highlights
- Global Head of Product at Square, owns product strategy across the seller ecosystem
- Leads a $4B+ business, grew payment volume 20%+ through new pricing, packaging, and growth programs
- Leads a 100-person product org inside Square's 3,000-person development organization
- Comfortable leading at any scale, from 2-person teams to orgs of hundreds
- Grew from engineer to GM to product executive across a 12-year arc at one company
- Shipped Square's first AI products: Square Assistant, Managerbot, Square AI, Voice AI
- Built and ran three P&L-carrying product lines as General Manager
- Scaled products from zero to billions in gross payment volume
- CTO of BookFresh, acquired by Square
- Writes and speaks publicly on AI, product development, and commerce
Work
Square
2014 – present
Global Head of ProductMar 2025 – present
Head of Product, Audiences, Dashboard & Commerce Platform2024 – 2025
General Manager2019 – 2024
Director of Engineering2014 – 2019
- Leads a $4B+ business across the seller ecosystem, owning product strategy and business outcomes
- Leads a 100-person product team within Square's 3,000-person development organization
- Launched Square's combined super app POS, unifying restaurants, retail, and services into one platform
- Shipped new hardware generation including Handheld and Register v2
- Launched new pricing & packaging and growth programs that grew payment volume 20%+
- Drives Square's AI product roadmap, shipping Managerbot, Square AI, and Voice AI
- Leading agentic commerce initiatives across MCP, ACP, and UCP
- Defined Square's vertical software strategy for restaurants, retail, beauty, and services
- Scaled Square Appointments into the company's largest vertical product
- Shipped Square's first LLM deployment with Square Assistant
- Built engineering teams from scratch for Appointments, Invoices, and Virtual Terminal
- Took products from launch to billions in gross payment volume
- Shipped 3 mobile apps, each reaching hundreds of thousands of merchants
- Chaired Engineering Levels & Promotion committees, interviewed 200+ engineers
BookFresh (acquired by Square)
Co-founder & CTO · 2011 – 2014
- Built online scheduling and POS software for small and medium businesses
- Grew engineering team to 6, owned both engineering and product
- Pivoted to cloud infrastructure and migrated from PHP to Ruby
- Acquired by Square in 2014
InQuira (acquired by Oracle)
Director, then Solution Architect · 2006 – 2011
- Led development for end-user-facing web applications, modernized Java/J2EE stack
- Part of 4-person technical due diligence team during Oracle acquisition
- Built and launched natural language search and knowledge management platforms
Education
Rochester Institute of Technology
BS, Computer Science · 2000 – 2004
Computer Science House, RIT Center for Discovery Informatics
Writing
Essays at Willem's Avenue on product development, AI, management, and technology.
Selected Public Work
- Decoder with Nilay Patel: Square's product chief on the death of the penny and the future of money
- Tech Talks: The Truth About Scaling AI to the Corner Shop
- Spring 2025 Square Releases
- Building With You: Our Public Roadmap
- Build a Stronger Network and Reliable Connectivity
- How Smarter Setup and Troubleshooting Tools Are Giving You More Control
Open Source
- newsbuddy — AI-powered knowledge companion for articles, podcasts, feeds, and URLs
- researchbuddy — Research-oriented AI project built around synthesis and exploration
- writing_buddy — AI writing assistant with multiple critique agents