About the Role 99Pledges a fundraising technology platform that powers online donation campaigns for organizations, teams, and individuals through our flagship product and through white-label deployments for partners. We're looking for a Senior Software Engineer who thrives in a mature, production Rails codebase, cares deeply about payment integrity, and can own features end-to-end from database schema to background jobs to the user-facing UI. Integrations with multiple payment providers (credit card, PayPal, and ACH/EFT), including automatic payouts, payment requests, and reconciliation.

Branding, feature flags, and configuration that let partners run the platform under their own identity.

Fraud prevention & trust : Fraud detection, device fingerprinting, and abuse mitigation that keep donors and organizations safe. Reliable email delivery, data exports, and scheduled metric calculations. Ruby on Rails 7, Ruby 3.1 Database : PostgreSQL (production), with careful attention to migrations and denormalized/calculated fields for performance Frontend : HAML, SCSS, Bootstrap, jQuery Infrastructure : Heroku, AWS S3, Redis Monitoring : Honeybadger (errors), New Relic (performance), Datadog (migrating to) 3+ years building and maintaining production web applications, with strong Ruby on Rails experience. ~ Solid grasp of relational database design, query performance, and safe migrations against large production tables. ~ Experience integrating third-party APIs, ideally payment processors, and an appreciation for the failure modes that come with them (retries, idempotency,



webhooks, reconciliation). ~ A test-first mindset, you write well-tested code and treat correctness and edge cases as first-class concerns. ~ Comfort working across the stack, including server-rendered views and front-end interactivity. ~ Solid communication skills and the ability to explain technical tradeoffs clearly.

Experience with payment/fintech systems, PCI considerations, or handling money in software. Exposure to fraud detection or trust & safety systems.

We take production seriously: careful migrations, monitoring, and a bias toward correctness — because we handle donations that matter to real people and organizations.

Why Join Us You'll work on software that helps organizations raise money for causes they care about, with a small team where your work has direct, visible impact on both the product and the people who depend on it. Business is a repeat game and we believe that human relationships generate alpha. We take pride in having a deep sense of responsibility to ourselves, each other, our partners, and our customers. We seek to build a generational software company.

How We Use AI in Our Hiring Process: To ensure transparency, we want candidates to know that the company uses Artificial Intelligence and AI-enabled tools to assist with screening, reviewing, organizing and highlighting profiles and applications that match the key requirements for each role.

AI does not make hiring decisions: We use AI to support efficiency and consistency, not to replace human judgment.

📌 Senior Software Engineer - Configuration (Toronto)
🏢 United States Digital Space
📍 Toronto