Rob O'Dwyer

Senior Software Engineer: Cloud Infrastructure, DevOps, and Automation

Profile

Software engineer with 15+ years of experience spanning startup CTO, Principal Engineer at Workday, and independent infrastructure consulting. Specialized in large, complex cloud migration projects. Highly experienced in platform infrastructure and DevOps, with a focus on solving complex problems that drive core app requirements including performance, reliability, and migrations.

Experience

Senior Software Engineer

Feb 2025 - Present
Whalesync

Owned product and infrastructure projects end to end for a real-time data sync platform, using AI assisted development to migrate integrations used by hundreds of customers successfully.

  • Migrated sync integrations to new infra using an AI-assisted harness with automated validation of production data.
  • Researched and developed features powered by generative AI to streamline the experience of setting up a Whalesync sync.

Cloud Infrastructure & DevOps Consultant

Jan 2024 - Feb 2025

Led cloud-based infrastructure migrations for three startups:

  • Whalesync: Migrated production and staging infrastructure from AWS to GCP with no data loss or disruption to customer's sync operations.
  • WATS: Built an automated deploy pipeline on AWS.
  • OtherSphere: Built automated deploy pipelines and observability tooling.

Senior Software Engineer

Mar 2023 - Jan 2024
DevCycle

Implemented SDKs in multiple languages, built new features for the DevCycle feature flag platform, and maintained DevCycle and Taplytics infrastructure.

  • Partnered with a flagship customer to optimize the Go SDK for their low-latency use case, and succeeded in achieving the goal of sub-50-nanosecond 90th percentile lookups across their production fleet.
  • Built automated release pipelines on GitHub Actions for Go, Python, JavaScript, and Java SDKs to maximize platform compatibility.
  • Supported the team's successful SOC 2 audit by documenting architecture, fixing security gaps, and running gameday exercises with the developer team.

Senior Software Developer

Aug 2021 - Mar 2023
Battlesnake

Developed and scaled the Battlesnake game engine server and global proxy system.

  • Built out a global multi-datacenter proxy system to calculate player latency more equitably.
  • Engaged with a worldwide developer community of thousands through open source contributions and community discussions.

Principal Software Engineer

Nov 2017 - Aug 2021
Workday

Developed cloud services for processing video and interactive learning content.

  • Led the zero-downtime migration of a highly sensitive production service along with customer data from the Workday datacenter to AWS.
  • Interviewed, trained, and mentored a 3-person developer team in Dublin, Ireland. Established a satellite team to provide support EU-based partner teams and implement follow-the-sun support practices

CTO

Jun 2013 - Jul 2017
Pretio Interactive

Technical co-founder, responsible for developing Pretio's core technology and growing the development team. Pretio Interactive was an ad-tech startup that combined machine learning and consumer preferences to serve personalized ads.

  • Recruited and trained development team while building the technology platform for Pretio's advertising network.
  • Designed and built a high throughput HTTP server in Go for integrating into real-time bidding networks, and successfully scaled it to operate at 10K requests/second.
  • Researched and implemented online machine learning techniques to optimize profitability.

Software Engineer

Sep 2011 - Jun 2013
Entrepreneurship@Alacrity

The Entrepreneurship@Alacrity program provided an intense training environment to prepare graduates for entrepreneurship in the technology sector.

Education

MASc in Electrical and Computer Engineering

2012 - 2017
University of Victoria

BASc in Computer Engineering

2006 - 2011
University of British Columbia

Skills

AI Engineering

LLM API integration (Claude, OpenAI) • AI-assisted migration tooling • Agent workflow design

Languages

Python • Go • TypeScript • JavaScript • Node.js • Java • C/C++

Cloud and DevOps

Docker • Terraform • Amazon Web Services (AWS) • Google Cloud Platform (GCP) • Kubernetes • GitHub Actions • GitLab

Databases

Postgres • MySQL • Redis

Front-end

HTML/CSS • TypeScript/JavaScript • React