Dillon O'Leary

Dillon O'Leary

Tech Lead / Senior Software Engineer · New York City

SKILLS

PROFICIENT

Backend Engineering (Python, FastAPI, PostgreSQL) · Technical Leadership · AI Agents (Pydantic AI, Claude Code) · DevOps & Cloud (AWS, GCP, CDK, CI/CD, observability)

INTERMEDIATE

Distributed Systems (async pipelines, message queues) · Full-Stack (TypeScript, Next.js)

EXPERIENCE

Tech Lead / Software Engineer — CEART

Dec 2024 – July 2026 · New York, NY

Now advising part-time for equity.

  • Joined as a backend engineer and became tech lead in early 2025 as the company grew from four to twenty, leading seven engineers and helping hire.
  • Owned the core analysis engine of a clean-energy diligence platform: multi-agent systems on Pydantic AI running Claude, Gemini, and OpenAI models. Async task pipelines turn 0.5–10 GB datarooms of PDFs, spreadsheets, and scans into structured analysis that mirrors how analysts actually conduct diligence.
  • The engine evaluated about 40 clean-energy projects representing over $7B in assets for competing infrastructure funds, and its findings informed investment decisions, including passes.
  • Ran production on GCP and Railway with Logfire observability: dashboards, structured logging, and alerting that catches pipeline failures and files tickets automatically.

Software Engineer (Consulting) — School District 197

2024 – Present · Minnesota

West St. Paul-Mendota Heights-Eagan Area Schools; first engagement 2020.

  • Pitched and led an open-source immunization-records pipeline. A records sync that took 2–6 hours of manual work, and happened monthly at best, now takes about 10 minutes and runs weekly, or daily when needed, across a 5,000-student district. Districts across Minnesota are looking to integrate this system as well.
  • Designed it with the people who use it: user interviews across district staff, close work with the head of nursing, and coordination with the state immunization registry (MIIC), keeping records inside the district’s privacy standards.
  • In 2020, proposed and built the district’s COVID-19 case tracker on Google Workspace, keeping it inside tools the district already trusted; it informed leaders deciding whether schools stayed open and inspired other districts.

Volunteer Tech Lead — Digital Aid Seattle

Dec 2023 – Jan 2025 · Seattle, WA
  • Led ten volunteer engineers building a full-stack animal shelter intake system for Seattle Humane in Next.js and Supabase, handling recruiting, onboarding, and coordination.

Software Development Engineer — Amazon

Apr 2021 – Mar 2023 · Seattle, WA
  • Restructured documentation for Amazon’s core ordering platform (5–10 high-severity tickets daily) so platform users could answer their own questions, cutting on-call burden.
  • Built a Python manifest-generation tool that let auditors inspect the AWS Lambda functions behind Amazon’s global carbon-emissions reporting, supporting the annual sustainability report.
  • Helped run CI/CD for global deployments serving 1,000+ developers: code review, automated testing, and infrastructure as code (CDK, CloudFormation) across a hundred-plus dependencies.

EDUCATION

B.A. Computer Sciences & Psychology (double major)

2016 – 2020

University of Wisconsin–Madison. Graduated with Distinction, Distinction in both majors, GPA 3.8.