Konstantin Gredeskoul
Principal AI-first Engineer, ex-CTO, with 20+ years shipping distributed systems. C/C++, Ruby, Go, React; Python. Excels in systems thinking, data modelling, AI Agents, Applied AI projects, Vector Search and more.
- Role
- Principal Engineer at Archive
- Location
- San Francisco, CA, US
- LinkedIn followers
- 500 followers
About Konstantin Gredeskoul
Staff/Principal Engineer and 4x startup CTO with a math background. I turn ambitious product bets into reliable, scalable systems by keeping designs simple, metrics meaningful, and feedback loops fast. I’ve led teams through rewrites, growth, and production chaos, while mentoring engineers into stronger owners.HighlightsWanelo: Led a full platform rewrite from a ~100K-line Java prototype to a ~10K-line Rails app with a 6-engineer team in 2 months while sustaining 99.99% uptime. Supported 100x traffic growth → req/min) and 25M active users.Leadership across ModCloth (Walmart acquisition), Blurb, and Drop In Media (co-founder/CTO), scaling teams up to 20 engineers and shipping under real-world constraints.Recent work (Fractional AI)Built a production recommendation system for an apparel storefront platform (uniform programs, sports clubs, team shops) using Python + PostgreSQL, combining pgvector semantic search with sales/ranking signals for practical store-owner outcomes.Delivered a fully automated, zero-downtime refresh pipeline reloading from source pgdump exports to keep recommendations current without interruption.Built an AI automation connecting Slack + Notion to monitor channels and extract actionable to-dos automatically.I’m comfortable deep in the weeds (PostgreSQL at multi-billion-row scale, reliability/performance, CI/DevEx automation) and at the architecture/strategy level. Open source is a long-running habit: 40+ Ruby libraries with 200M+ downloads, plus contributions to tooling like Bazel.Next: AI-enabled platforms and data products, especially recommendation systems, LLM-powered workflows, inference/tooling, and pragmatic ML infrastructure (Python/Go).
Experience
Principal Engineer
Apr 2026 — Present · US
Agentic AI, Terabytes of data, proven business model.
Education
Monash University
BSc (Hons), Pure Mathematics, Statistics
1992 — 1995
Harkivs'kij Deržavnij Universitet im. I.P. Kotljarevskogo
BSc, Mathematics (transferred after 1 year)
1991 — 1992
Skills
- Jquery
- Web Applications
- Java Enterprise Edition
- Enterprise Software
- Enterprise Architecture
- Software Development
- Databases
- Architecture
- Start-Ups
- Test Driven Development
- Apis
- Continuous Integration
- Spring
- Ruby on Rails
- Architectures
- Java
- Arduino
- Ruby
- Postgresql
- Mysql
- Integration
- Cloud Computing
- Agile Methodologies
- Scalability
- Software Engineering
- Redis
- Devops
- Web Development
- Git
- Performance Tuning
- Mentoring
- Mobile Applications
- Message Queue
- Javascript
- Solr
- Sql
- Linux
- Hibernate
- Service-Oriented Architecture (Soa)
- Xml
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