Insights on engineering leadership, AI infrastructure, Web3, and scaling technology organizations. https://johnjaewoolee.com/writing en-us Tue, 17 Mar 2026 00:00:00 GMT john@johnjaewoolee.com (John Jae Woo Lee) john@johnjaewoolee.com (John Jae Woo Lee) https://johnjaewoolee.com/writing/igaming-prediction-markets-technology.html How real-time wagering platforms, prediction markets, and sportsbooks are built — from odds engines to settlement systems. An operator's perspective on the technology that makes these platforms work. Tue, 17 Mar 2026 00:00:00 GMT https://johnjaewoolee.com/writing/igaming-prediction-markets-technology.html https://johnjaewoolee.com/writing/fractional-cto-igaming.html iGaming and prediction market startups face unique technical challenges — real-time systems, regulatory compliance, and player trust. Here's when a fractional CTO makes sense and what to look for. Tue, 10 Mar 2026 00:00:00 GMT https://johnjaewoolee.com/writing/fractional-cto-igaming.html https://johnjaewoolee.com/writing/scaling-engineering-teams.html A first-hand account of scaling engineering organizations through every inflection point — from 4 engineers at Riot Games to 90+ at Sky Mavis. Org design, delivery systems, and the leadership shifts that matter. Thu, 15 Jan 2026 00:00:00 GMT https://johnjaewoolee.com/writing/scaling-engineering-teams.html https://johnjaewoolee.com/writing/fractional-cto-playbook.html A practical guide to fractional CTO engagements — when to hire one, what to expect, engagement models, and how to get executive-caliber engineering leadership without full-time overhead. Thu, 29 Jan 2026 00:00:00 GMT https://johnjaewoolee.com/writing/fractional-cto-playbook.html https://johnjaewoolee.com/writing/building-llm-infrastructure.html Infrastructure-first thinking for AI and LLM systems. Lessons from building at Amazon Lab126 through today's generative AI landscape — architecture patterns, build vs. buy decisions, and real costs. Thu, 12 Feb 2026 00:00:00 GMT https://johnjaewoolee.com/writing/building-llm-infrastructure.html https://johnjaewoolee.com/writing/engineering-leadership-web3.html Leading 72 engineers at Chainlink Labs and 90+ at Sky Mavis taught me what's different about Web3 engineering leadership — and what stays exactly the same. Thu, 26 Feb 2026 00:00:00 GMT https://johnjaewoolee.com/writing/engineering-leadership-web3.html https://johnjaewoolee.com/writing/founding-engineer-to-head-of-engineering.html The personal journey from writing the first line of code at Caffeine.tv to leading the entire engineering function through Series D. Identity shifts, delegation, and the mistakes I made along the way. Thu, 05 Mar 2026 00:00:00 GMT https://johnjaewoolee.com/writing/founding-engineer-to-head-of-engineering.html https://johnjaewoolee.com/writing/technical-due-diligence.html A structured framework for evaluating engineering quality during investment due diligence. The 5 pillars, red flags, green flags, and questions to ask — from an operator who has been on both sides. Sun, 15 Mar 2026 00:00:00 GMT https://johnjaewoolee.com/writing/technical-due-diligence.html