Skip to content
View madoleary's full-sized avatar
🤠
🤠

Block or report madoleary

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.

Content in all repositories owned by your account will be closed.
Maximum 250 characters. Please don’t include any personal information such as legal names or email addresses. This note will only be visible to you.
Report abuse

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

Report abuse
madoleary/README.md

Madeline O'Leary

Senior product engineer with 9+ years of experience building production web applications, primarily in Ruby on Rails.

I work best on small teams where I can stay close to the code, help shape the product, and own consequential technical decisions from architecture through release. My experience includes automated purchasing and payments, identity and access systems, public-interest platforms, third-party integrations, and production operations.

Current focus

  • Backend architecture and product engineering with Ruby on Rails
  • Reliable background processing and third-party integrations
  • Payment, purchasing, identity, and authorization systems
  • Practical uses of AI-assisted engineering with careful human review

Selected work

SeatSnags

Founding Engineer (Contract) | December 2025 - August 2026

Designed and built the complete Rails backend for an automated ticket-purchasing platform released to trusted users through TestFlight.

  • Architected purchasing across Ticket Evolution and Stripe, including explicit lifecycle states, concurrency controls, idempotency safeguards, signed webhooks, reconciliation, and failure recovery.
  • Enforced customer price, quantity, section, and delivery constraints at purchase time.
  • Defined API contracts with the frontend engineer and led integration testing, controlled real-money validation, and production hardening.

Terms of Service; Didn't Read (ToS;DR)

Founding Engineer and Maintainer, Phoenix Platform | 2017 - 2025
Varying contract and open-source involvement

Built and maintained Phoenix, the contributor platform that powers ToS;DR's community review of online services' terms and privacy practices.

  • Built the Phoenix MVP and helped design and lead implementation of its annotation system.
  • Integrated a substantially customized Hypothesis instance, including authentication, data migration, and coordinated annotation changes across both applications.
  • Helped develop document collection and historical change tracking for thousands of terms-of-service documents across hundreds of services.
  • Led contributor validation and communication for a major annotation-system migration.

Phoenix repository

International Consortium of Investigative Journalists

Full-Stack Engineer (Contract) | June 2018 - January 2022

Built and secured systems supporting confidential collaboration among hundreds of investigative journalists worldwide.

  • Took architectural ownership of Xemx, ICIJ's identity gateway, including LDAP-backed onboarding, single sign-on, PGP setup, and investigation-specific authorization.
  • Built YubiKey authentication by extending Devise and integrating WebAuthn.
  • Developed a substantial Discourse plugin that enforced investigation boundaries, including direct-link access, and backed the restrictions with automated tests.

The relevant repositories are private because of newsroom security requirements.

Bluesquare

Full-Stack Engineer (Contract) | January 2022 - February 2023

  • Built Rails APIs and React interfaces for software used to calculate, report, and administer performance-based health financing.
  • Modernized frontend data management with React Query.
  • Built reusable React and Tailwind components for invoicing and reporting applications used by on-the-ground health-program administrators across sub-Saharan Africa.

ORBF2 repository

Technical skills

  • Backend: Ruby, Ruby on Rails, Python, Django, Pyramid, REST API design
  • Frontend: JavaScript, React, Vue, Ember, React Query, Tailwind CSS; working knowledge of TypeScript
  • Data and infrastructure: PostgreSQL, Redis, Elasticsearch, Docker, AWS, Sidekiq, Ansible
  • Testing and security: RSpec, Jest, WebAuthn, SSO, LDAP, PGP, application security

Outside engineering

I also wrote, directed, and produced the award-winning short film Flirtologist. Filmmaking is part of my background, but engineering is my professional focus.

Film awards

Popular repositories Loading

  1. DeleteFB DeleteFB Public

    Forked from weskerfoot/DeleteFB

    A Selenium script to delete your Facebook content.

    Python 1

  2. git101 git101 Public

    HTML

  3. dotfiles dotfiles Public

    Forked from lewagon/dotfiles

    Default configuration for Le Wagon's students

    Shell

  4. profile profile Public

    HTML

  5. json-convert-csv json-convert-csv Public

    Ruby

  6. 1901 1901 Public

    Forked from tosdr/paperwork

    Associaton Terms of Service; Didn't Read (non-for profit org, registered in France)

    HTML