Skip to content
View kigster's full-sized avatar
:octocat:
Pushing AI automation into production.
:octocat:
Pushing AI automation into production.

Highlights

  • Pro

Block or report kigster

Block user

Prevent this user from interacting with your repositories and sending you notifications. Learn more about blocking users.

You must be logged in to block users.

Maximum 250 characters. Please don't include any personal information such as legal names or email addresses. Markdown supported. This note will be visible to only you.
Report abuse

Contact GitHub support about this user’s behavior. Learn more about reporting abuse.

Report abuse
kigster/README.md

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 • PostgreSQL

ResumeBlogConsultingLinkedInGitHubRubyGemsTalksSlideShare


About Me

I’m a hands-on Staff / Principal-level software engineer and former CTO who builds reliable, scalable production 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 networked version running on Google Cloud Run, which offers a ReactJS frontend to the C99/HTTPD backend via JSON API. 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

  • 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

Pinned Loading

  1. cmake-project-template cmake-project-template Public

    This project is aimed at jump-starting a C/C++ project that can build libraries, binaries and have a working unit test suite. It uses CMake build system and is deliberately completely minimal.

    C++ 949 259

  2. simple-feed simple-feed Public

    This gem implements a flexible time-ordered activity feeds commonly used within social networking applications. As events occur, they are pushed into the Feed and distributed to all users that need…

    Ruby 335 31

  3. sym sym Public

    Sym is a command line utility and a Ruby API that makes it trivial to encrypt and decrypt sensitive data. Unlike many other existing encryption tools, sym focuses on usability and streamlined inter…

    Ruby 138 9

  4. puma-daemon puma-daemon Public

    Puma (starting version 5) removed automatic demonization from the gem itself. This functionality was extracted to this gem, which supports Puma v5 and v6.

    Ruby 39 8

  5. bashmatic bashmatic Public

    Optimized for humans, 900+ BASH DSL functions for all walks of life. Über Toölkit for über geeks and UNIX command line power users. Visit https://bashmatic.dev for more info..

    Shell 176 19

  6. gomoku-ansi-c gomoku-ansi-c Public

    This repo contains both the ASCII Terminal implementation of the Gomoku game, with MiniMax algorithm & Alpha/Beta pruning. It only requires arrow keys to choose and Enter to make a move. Separately…

    C 2 1