David Byron Drake

David Byron Drake

Engineering leader building AI-native products. Former YC CTO.

Engineering leader with nearly two decades of experience spanning startup CTO and director roles. I build and lead teams that ship production AI systems, full-stack platforms, and developer infrastructure at scale — currently looking for engineering leadership roles where AI strategy and hands-on technical depth both matter.

🎯 Director / VP of Engineering & AI strategy 🌎 Remote-first · Portland-area hybrid 📍 Tigard, OR

GitHub at a glance

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Experience

~18–20 years · Theatre → teaching → engineering → startup CTO/CEO → eng leadership
DevOps & Engineering Manager
Counterpart
Dec 2024 – Mar 2026

Led three teams (two full-stack + DevOps); drove Agile delivery to 89%, well above the 70% benchmark. Built MCP infrastructure integrating seven platforms across the insurance lifecycle; owned SOC 2 / HIPAA; saved ~$20K/yr with a git-tracked Salesforce CI/CD pipeline.

Leadership · MCP · SOC 2 / HIPAA
Director of Engineering
Flourish Software
Jul 2021 – Oct 2024

Led teams of up to 15 engineers across three countries on a large-scale supply-chain platform (Go, Angular/TypeScript, AWS, Kubernetes). +60% on-time delivery, −50% support load.

Go · Angular · AWS · Kubernetes
Senior Full-Stack Engineer
Expensify
May 2018 – Jul 2021

Secured receipts across six stacks (C++, PHP, Java, iOS, Android, JS), moving millions of dollars daily and handling thousands of requests per second at Super Bowl–scale traffic.

High-scale · Multi-stack
Founder & CEO
RedDep Labs
Oct 2013 – May 2018

Led a 17-person team across HR, sales, and engineering. Built an open product-data platform — tens of thousands of catalogued products and a public API used by 400+ developers — scaling to 10M hits/month on a single server and an $8.6M valuation.

Founder · Open API · Scale
Chief Technology Officer
iCracked · Y Combinator
Mar 2013 – Oct 2013

CTO over the company; built a pioneering dispatch system coordinating 400+ technicians nationwide and drove a ~30% increase in conversion.

YC · Marketplace · Ops

What I do

Leadership
People management Hiring & talent development Performance management Cross-functional collaboration Stakeholder communication Agile / Scrum Psychological safety Radical candor Extreme ownership
Languages & frameworks
Python TypeScript React Tailwind Angular Go Java C++ SQL PHP / Laravel D3.js Shell
Infrastructure & tools
AWS Kubernetes Docker PostgreSQL MySQL Redis Snowflake GitHub Actions ETL pipelines Salesforce
AI & practices
Claude OpenAI AI enablement & training Agentic development LLM infrastructure Custom MCP servers Prompt engineering AI governance DevOps & CI/CD SOC 2 / HIPAA

Repositories

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