Head of Engineering / CTO — LandTrust

June 2023 – Present

Own engineering strategy and execution for a marketplace platform connecting landowners and outdoor enthusiasts. Focused on product growth, AI-driven systems, operational discipline, and platform ownership.

Business Impact

• Increased GMV by 50%+ year-over-year
• Improved engineering delivery success rate from 50% to 90%
• AI chat platform (Buck) now influences 20% of inquiries and bookings, with usage growing 50% in the last 2 months despite partial rollout
• Improved search result click-through rate by 30%
• Increased organic search impressions 5x over 6 months, with clicks up 60% and average position improving by 33%
• Achieved consistent “Good” Core Web Vitals across the platform with no poor URLs reported by Google
• Reduced potential AWS infrastructure costs by ~25% through governance and optimization initiatives
• Reduced image delivery costs by 50% through bandwidth optimization initiatives

Platform & Technical Leadership

• Led development and rollout of Buck, an AI-driven conversational platform integrating retrieval, operational tooling, and event-driven workflows
• Built centralized data pipelines capturing platform activity for analytics, automation, and AI systems
• Developed internal AI knowledge platform integrating GitHub commits, Basecamp data, operational documentation, and log-query tooling using CloudWatch and Athena
• Established Terraform as the standard for infrastructure management, achieving full coverage for new services and security systems
• Reframed migration away from Sharetribe into an incremental platform ownership strategy, selectively taking control of reviews, messaging, notifications, and data flows
• Built a component library and design system with accessibility and performance standards built into the development workflow

Security & Operational Excellence

• Led response and resilience improvements during DoS attacks and fraud attempts while maintaining roadmap delivery
• Expanded monitoring, observability, and operational governance across AWS infrastructure
• Increased engineering leverage through AI adoption and internal tooling without increasing full-time engineering headcount

Software Development Manager — Amazon Web Services (AWS)

May 2022 – June 2023

Led an engineering team responsible for desktop streaming applications across Windows, macOS, Linux, iOS, and Android for AWS WorkSpaces.

• Managed an 8-person engineering team focused on delivery execution, reliability, and customer experience
• Improved release cadence and operational efficiency through automation and process improvements
• Reduced support burden through workflow optimization and improved issue prioritization
• Delivered accessibility initiatives across platforms ahead of schedule
• Partnered closely with product and leadership stakeholders to align roadmap priorities and delivery execution

Director, Enterprise Platform — LTK (formerly RewardStyle)

April 2021 – April 2022

Led platform engineering initiatives focused on developer enablement, DevOps maturity, identity systems, and architectural governance.

• Built and led a platform engineering team responsible for CI/CD, identity infrastructure, API management, and developer tooling
• Led migration initiatives involving GitHub Actions, GitHub Advanced Security, and Auth0
• Established engineering standards, governance processes, and architecture review practices
• Introduced operational visibility and support measurement processes across platform services
• Served on the company’s Reference Architecture Council

Director of Engineering / Architect — Rakuten Advertising

2010 – 2021

Led engineering organizations and platform architecture initiatives supporting large-scale affiliate marketing and advertising systems.

Engineering Leadership

• Managed and scaled international engineering teams of 30+ engineers across multiple functional areas
• Led hiring and onboarding initiatives that added 12 engineers within 12 months
• Drove organizational transformation initiatives around DevOps, cloud adoption, engineering standards, and service management
• Established engineering processes and governance models improving visibility, operational consistency, and delivery effectiveness

Platform & Architecture

• Led early adoption of AWS and containerization strategies that accelerated infrastructure modernization and developer autonomy
• Implemented centralized authentication and authorization platforms using Keycloak
• Established API gateway and policy enforcement strategies using Kong, standardizing logging, monitoring, rate limiting, and service governance across engineering teams
• Developed common service review and continual service improvement processes across 25+ engineering teams
• Led architecture and development efforts for affiliate network platforms, reporting systems, partner integrations, and customer-facing applications

Industry & Technical Leadership

• Presented at MongoDB World in 2015 and 2016
• Conducted Behavior Driven Development workshops for engineering organizations and educational programs
• Championed engineering culture shifts emphasizing developer autonomy, DevOps practices, and cross-functional collaboration