Lead Engineer- 99Pledges
AI summary of the role
Lead Engineer role for 99Pledges, a profitable K-12 fundraising platform processing ~$100M/year.
What you’ll do
- Set the technical roadmap with GM, product, and customers
- Own payment integrations, payouts, reconciliation, and fraud handling
- Ship AI features to production with evals and guardrails
- Raise engineering standards: CI, staging, feature flags, test coverage
What you’ll bring
- Production experience handling money (payments, payouts, reconciliation, fraud)
- Sole ownership of a real system (design, build, deploy, on-call)
- Postgres depth: modeling, tuning, zero-downtime migrations
- Shipped LLM features to production (retrieval, tool use, evals)
Technologies
Ruby on Rails · PostgreSQL · Braintree · PayPal · Dwolla · Stripe · Heroku · AWS S3 · Redis · Delayed Job · HAML · jQuery
Source and classification
Production engineering · Evidence for this classification:
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 $100M 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. The Role You would be the only engineer on 99Pledges. Architecture, deploys, incidents, vendor calls, and prioritization all sit with you. There is no one to hand work to, so the job rewards people who automate aggressively and pick their battles. What You'll Do Set the roadmap. With the GM, the product team, and customers, decide what gets built. Turn business priorities into a
More from the job description
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 $100M 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. The Role You would be the only engineer on 99Pledges. Architecture, deploys, incidents, vendor calls, and prioritization all sit with you. There is no one to hand work to, so the job rewards people who automate aggressively and pick their battles. What You'll Do Set the roadmap. With the GM, the product team, and customers, decide what gets built. Turn business priorities into a sequenced plan and explain the tradeoffs. Get the money right. Donations, automatic payouts, and reconciliation across several payment providers. Retries, idempotency, webhooks, and handling a provider that degrades in the middle of a 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 and when a deterministic pipeline is. Use AI on your own work. You are one person, so your output is the limit. We ex [... source excerpt omitted ...] the follow-up that stops it recurring. What We're Looking For A senior generalist. You move across web, data, infrastructure, and AI, and you pick up unfamiliar stacks quickly. Production experience handling money. Payment integrations, payouts, reconciliation, or fraud work, and familiarity with how these fail. This is the requirement we bend on least. 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. You can model, query, and tune production Postgres, and you have run migrations against large tables without downtime. [... source excerpt omitted ...] unpleasant to look at. Clear writing. Working alone, writing is how everyone else knows what is happening. Tech Stack 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 Why Join Us You'll work on software that helps organizations raise money for causes they car
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