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kigster - Overview

I build systems that survive exponential growth, handle ambiguity, and are resilient to human optimism.

-- KG.

Konstantin Gredeskoul

Staff / Principal Software Engineer • AI Systems • Distributed Architecture • Ruby • Python • TypeScript • PostgreSQL

Resume • Blog • Consulting • LinkedIn • GitHub • RubyGems • Talks • SlideShare

About Me

I’m a life-long coder, with a diverse career, who is currently a hands-on Staff / Principal-level software engineer and former CTO who builds and delivers to production reliable, scalable, and fault tolerant systems.

My background spans distributed systems, PostgreSQL, Ruby/Rails, infrastructure, developer productivity, and, more recently, applied AI systems: retrieval pipelines, eval harnesses, production automation, and embedding-based services.

I like hard problems with real constraints:

  • scaling transactional systems
  • eliminating operational risk
  • improving developer experience
  • shipping AI features without turning the product into a probabilistic mess

What I Do

  • Build and scale large distributed backend systems with strong reliability and observability baked in
  • Design production AI workflows around real business use cases
  • Improve CI/CD, onboarding, deployment safety, developer productivity, and operational simplicity
  • Comfortable in all levels of abstractions, from back-of-the-napkin architecture, to nitty-gritty code details.
  • Turn messy systems into maintainable ones, and have successfully rewritten systems from scratch under two months.
  • Practice 90%+ test coverage and will convince you to do the same.

Selected Highlights

Important

  • 4x CTO / technical leader with decades of experience across startups and growth-stage companies
  • Helped scale a consumer platform from a fragile prototype to a Rails system handling massive growth with 99.99% uptime
  • Achieved 100% uptime during ACA open enrollment at HealthSherpa under major traffic spikes
  • Averted a potentially catastrophic PostgreSQL transaction wraparound incident on a 27TB database
  • Built applied AI systems in production, including:
    • recommendation systems using Python, PostgreSQL, and pgvector
    • embedding refresh pipelines with zero-downtime cutovers
    • internal AI automation for workflow extraction and follow-through
  • Created and maintained Ruby open source projects with 200M+ cumulative gem downloads
  • Co-created early Ruby rules for Bazel, contributing to the path toward modern Ruby support in Bazel ecosystems
  • Conference speaker on scalability, PostgreSQL, Ruby, and systems architecture

Current Technical Interests

  • Applied AI engineering
  • LLM product architecture
  • Evaluation-driven development
  • Retrieval and ranking systems, in particular Power Law distribution
  • PostgreSQL performance, scalability, replication architecture, and security
  • Ruby, Python, TypeScript, C/C++, BASH, Rust
  • Distributed systems, with high availability, fault tolerance, and auto-healing architectures
  • Developer tooling, automated onboarding, and build systems
  • Gaming Algorithms, Mini-Max, Alpha Beta Pruning
  • Networking Systems, CISCO routers, VLANs, etc.
  • Hardware, ESP32, Arduino, Raspberry PI, and more.

Open Source

A few projects that reflect the range of work I enjoy:

  • gomoku-ansi-c
    ANSI-C-based game engine for 5-in-a-row (or Gomoku) that runs in a TTY terminal, and you can play using arrow keys.

    Or, you can use the online version running on Google Cloud Run, which offers a ReactJS frontend talking JSON API to FastAPI Python server with PostgreSQL connectivity, which proxies game moves to q cluster of stateless single-threaded C99/HTTPD backends behind Envoy reverse proxy. Game API includes the entiee game state in the JSON hash. You can play the game here: app.gomoku.games

  • simple-feed
    Redis-backed social feed architecture similar to Twitter, with O(1) feed read-time property. scales to tens of millions of users.

  • colored2
    Terminal color support for Ruby

  • sym
    Symmetric encryption via CLI and Ruby API

  • puma-daemon
    Puma daemonization support

  • cmake-project-template
    C++ / CMake starter project with sensible defaults

  • bashmatic
    Bashmatic — 900+ DSL functions written in BASH for readable script feedback, terminal graphics, headers, and more.

You can also browse the full collection of public gems written in Ruby here:

Talks and Writing

I write and speak about:

  • PostgreSQL scaling
  • Ruby and systems design
  • developer productivity
  • DevOps and release engineering
  • applied AI systems

Some links:

Background

Originally from Kharkiv, Ukraine. Now based in the San Francisco Bay Area.

I graduated Suma Cum Laude from Monash University, majoring in pure mathematics and applied statistics, which permanently damaged my tolerance for fuzzy thinking.

Elsewhere