Konstantin Gredeskoul is a Principal Engineer and four-time startup CTO based in San Francisco with a math background and 18+ years of hands-on experience turning ambitious product bets into reliable, scalable systems. He has a track record of high-stakes platform rewrites and scale-ups—rebuilding Wanelo into a 10K-line Rails app that handled 100x traffic growth and sustaining 99.99% uptime, and guiding HealthSherpa to its first-ever 100% uptime during peak enrollment. Comfortable from multi-billion-row PostgreSQL tuning to CI/DevEx automation and pragmatic ML infrastructure, he recently shipped production recommendations with pgvector and zero-downtime refresh pipelines. A longtime open-source maintainer with 40+ Ruby libraries and contributions to Bazel tooling, he blends deep technical craft with team coaching and operational ownership. He’s attracted to AI-enabled platforms, LLM-powered workflows, and inference/tooling, and often moves between architecture strategy and “in-the-weeds” problem solving. An unusual strength: he repeatedly reduces system complexity and onboarding time—turning weeks of setup into hours while keeping designs simple and metrics meaningful.
9 years of coding experience
23 years of employment as a software developer
BSc, Mathematics (transferred after 1 year), BSc, Mathematics (transferred after 1 year) at Harkivs'kij Deržavnij Universitet im. I.P. Kotljarevskogo
BSc (Hons), Pure Mathematics, Statistics, BSc (Hons), Pure Mathematics, Statistics at Monash University
Contributions:2 releases, 38 commits, 13 pushes in 2 months
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