Lead Engineer- 99Pledges

About the role

The Business 99Pledges runs peer‑to‑peer fundraising campaigns for K‑12 schools and youth sports organizations: walk‑a‑thons, jog‑a‑thons, read‑a‑thons. It processes around $100 M in donations a year and serves roughly 5,700 organizations. It is profitable and growing, and it is the largest business in Beacon's education technology portfolio. Beacon buys established vertical software companies and puts real engineering leadership into them. Our engineers embed in one business and own its technology.

Responsibilities

• Set the roadmap – with the GM, product team, and customers decide what gets built; turn business priorities into a sequenced plan and explain the tradeoffs.
• Get the money right – handle donations, automatic payouts, and reconciliation across several payment providers; implement retries, idempotency, webhooks, and manage a provider that degrades mid‑campaign.
• Put AI into the product – move from plan to production (evals, guardrails, tenant‑safe tool use); know when a foundation model is the right call versus a deterministic pipeline; use AI on your own work; coding agents are expected to be part of your day‑to‑day.
• Raise the engineering floor – institute trunk‑based development, working CI, a staging environment on synthetic data, feature flags, real test coverage, and a deploy process that does not depend on your memory; write documentation so a second or third engineer can pick up the codebase quickly.
• Handle fraud and abuse – build fraud detection, device fingerprinting, and other safeguards to keep donors and schools safe.
• Watch the cost line – read cloud and vendor spend, identify waste, and judge whether fixing it is worth the time.
• Talk to non‑engineers – operators, school administrators, and partners will come to you directly.
• Hold the pager and own uptime – you own alerting that catches problems before organizers do, the response when something breaks at 7 am on a Saturday, and the follow‑up that stops recurrence.

Requirements

• Senior generalist – comfortable moving across web, data, infrastructure, and AI, and able to pick up unfamiliar stacks quickly.
• Production experience handling money – payment integrations, payouts, reconciliation, or fraud work, with familiarity of how these systems fail.
• Sole ownership of something real – you have been the only engineer, or the clear technical owner, on a system that mattered (design, build, deploy, on‑call, and the customer call when it broke).
• Postgres depth – able to model, query, and tune production Postgres, and run migrations against large tables without downtime.
• Shipped LLM features to production – experience with retrieval, tool use, evals, and guardrails; prototypes do not count.
• Track record of fixing engineering process – you have introduced trunk‑based development, automated testing, and environment discipline to a codebase that lacked them while still shipping.
• Judgment about technical debt – able to tell which debt is costing money and which is merely unpleasant to look at.
• Clear writing – working alone, writing is how everyone else knows what is happening.

Skills

• Backend: 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
• Background jobs: Delayed Job (Active Record backend)
• Payments: Braintree, PayPal, Dwolla, Stripe
• Infrastructure: Heroku, AWS S3, Redis
• Email: Postmark
• Monitoring: Honeybadger (errors), New Relic (performance), Datadog (migrating to)
• Analytics/experimentation: PostHog