Pete Keen

Staff Backend Engineer - Ruby/Rails, Distributed Systems, Payments & Fintech - Remote (US)

Backend engineer with 18+ years of experience going deep on complex systems to find the highest-leverage improvements. Led greenfield projects from design through deployment at Guideline, Gusto, and ClickFunnels; built payment and accounting systems processing millions of dollars; mentor and level up junior-through-senior engineers.

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Work Experience

Staff Software Engineer, 2023 - present

Gusto (formerly Guideline), fully remote

  • Tech lead for the Record Keeper team
  • Responsible for event-driven distributed systems, including three separate financial ledgers, tracking and transferring $13B in assets across more than 50,000 401(k) plans and millions of employee contributors
  • Designed, planned, and led the technical integration with a new banking partner, working cross functionally with staff engineers on two other teams to drive API design and implementation
  • Assumed ownership of an internal inbound webhooks platform, revising and improving to make it usable for our banking partner integration, and then transferred ownership to a newly created internal platforms team with strong internal adoption (~10 integrations across the organization)
  • Built an AI-assisted development workflow (Claude Code + custom tooling) and drove adoption across my team and the broader engineering organization
  • Partnered with Legal and Compliance on regulatory reporting
  • Mentored engineers from junior through senior as team tech lead

Principal Software Engineer, 2022 - 2023

ClickFunnels, fully remote

  • Designed and implemented the affiliates system for ClickFunnels 2.0
  • Implemented a double entry accounting system to support the affiliates and billing systems within CF 2.0
  • Refined internal tooling to make the spin-up and daily development processes for team members easier
  • Worked cross-functionally with other Principal Software Engineers to ensure development was coherent and on-track
  • Mentored senior engineers on system design and organizational interaction

Infrastructure Engineer, 2020 - 2021

Stripe, fully remote

  • Developed and maintained low level interfaces with AWS
  • Worked daily with Ruby, Python, Puppet, Terraform, and serverless AWS Lambda
  • Optimized and enhanced internal tools (recent ships: $2M annual compute savings; 1000x speed improvement during certain incident remediations; one-click React UI to lock puppet across all hosts in the fleet)
  • Planned, organized, and executed large migrations across the engineering organization (ex: coordinated base OS upgrade across dozens of teams and hundreds of Docker containers)

Software Engineer, 2019 - 2020

Stripe, fully remote

  • Migrated largest single financial partner to event-driven disputes platform
  • Adopted and maintained in-house PDF inspection and generation microservice written in Go

Software Developer, 2014 - 2019

egghead.io, fully remote

  • Led a small team of junior developers on building and maintaining the core Ruby on Rails backend platform
  • Built the accounting and revenue sharing system that pays millions of dollars to hundreds of instructors
  • Built the Stripe payments integration that processes millions of dollars a year for egghead
  • Directly worked with engineers at Fortune 500 companies to build a SAML service provider into egghead

Software Developer, 2012 - 2015

Kongregate, Portland OR

  • Maintained one of the largest and oldest Ruby on Rails applications in existence
  • Worked across the entire stack, from MySQL query optimization to Ruby and Node.js background jobs to front-end HTML, JavaScript and CSS
  • Implemented a lapsed-gamer mailer with customized messages for every user which increased retention by ~5%
  • Re-implemented several payment methods to use async background processing

Earlier Roles

  • Platform Developer at Emma, 2011 - 2012
  • Software Developer at Rentrak, 2007 - 2011

Consulting Experience

Independent Software Consultant (part-time), 2014 - present

Okapi Consulting, fully remote

  • Concurrent with full-time roles above
  • Debugged low-level WiFi issues for a small IoT device manufacturer
  • Audited the internal accounting system for a trucking-industry bookkeeping firm
  • Part-time CTO for a small software shop specializing in government training software
  • Migrated client applications to Docker and PaaS hosting platforms

Side Projects

  • VMSave, a Rails app for saving voicemail greetings as MP3s. Uses Twilio for telephony services, has been used over 20,000 times to date
  • Mastering Modern Payments, the first book about integrating Stripe payments with Rails, read by thousands of developers (Retired)
  • Handle Your Business, a book about what the nuts and bolts backend of a single person consultancy can look like
  • Docverter, an open source document conversion web service (Retired)
  • petekeen.net, my personal programming and tech related blog
  • Payola, a Rails engine for Stripe (Retired)
  • I have a small homelab where I play with things like local AI and LLMs, Docker, Kubernetes, CI/CD, and IPv6

Education

Bachelor of Science in Management Computer Systems

Computer Science Minor
University of Wisconsin - Whitewater
Graduated December 2006

Skills

  • Ruby, Rails, Python, Go, JavaScript, React, Java, Shell scripting, Node.js
  • Agile / Test-driven Development, Pair Programming, CI/CD, Event-driven Systems, Distributed Systems
  • AI-assisted development: Claude Code, Codex, LLM integration, agentic workflows, local LLMs (llama.cpp and Ollama)
  • Puppet, Terraform, AWS, EC2, Docker, Kubernetes
  • Git, SVN
  • Linux, macOS
  • PostgreSQL, MySQL, Redis, MongoDB