Senior Ruby on Rails Engineer — Own End-to-End Payments & AI

Beacon Holdings; United States; On-site; CAD 120,000 - 180,000; Full time

Job summary

99Pledges, Beacon Software’s standalone engineering lead for the education portfolio, seeks a lone engineer to own architecture, deployments, incidents, vendor calls, and prioritization. You will automate aggressively and decide what to build with input from the GM, product team, and customers.

You will ship end-to-end features, implement trunk-based development, maintain staging with synthetic data, feature flags, tests, and a deploy process that does not rely on memory.

Qualifications

• Senior generalist with web, data, infrastructure, and AI skills.
• Money handling experience: payments, payouts, reconciliation, or fraud.
• Sole ownership of a critical system: design, build, deploy, on-call, and customer contact when issues occur.
• PostgreSQL modeling, querying, and tuning under production load.
• Experience shipping LLM features to production (retrieval, tools, evals, guardrails).
• Established track record of improving engineering processes (trunk-based development, automated tests, environment discipline).
• Ability to judge technical debt costs and benefits.
• Strong, clear writing for team visibility and collaboration.

Responsibilities

• Set roadmap with GM, product team, and customers and translate into a sequenced build plan.
• Manage donations payouts, reconciliations across providers, retries, idempotency, and webhooks.
• Introduce AI into the product with production guardrails and deterministic pipelines.
• Code actively and apply automation in day-to-day work since you are the sole engineer.
• Drive trunk-based development, CI, staging with synthetic data, feature flags, and robust testing.
• Document code and tests so future engineers can pick up work quickly.
• Address fraud detection, device fingerprinting, and donor/school safety.
• Monitor cloud spend and vendor costs, deciding when fixes are worth the effort.
• Engage with operators, school admins, and partners directly to resolve issues.
• Own uptime and proactive alerting to catch problems before outages affect campaigns.

Skills

Senior generalist

Money handling

Ownership of real system

PostgreSQL proficiency

LLM features in production

Engineering process improvements

Technical debt judgment

Clear writing

Tools

Ruby on Rails

PostgreSQL

Heroku

AWS S3

Redis

Postmark

New Relic

Datadog

PostHog

Braintree

PayPal

Stripe

Job description

99Pledges, Beacon Software’s standalone engineering lead for the education portfolio, seeks a lone engineer to own architecture, deployments, incidents, vendor calls, and prioritization. You will automate aggressively and decide what to build with input from the GM, product team, and customers.

You will ship end-to-end features, implement trunk-based development, maintain staging with synthetic data, feature flags, tests, and a deploy process that does not rely on memory.