The RoleYou 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 expect coding agents to be part of how you work day to day.
- Raise the engineering floor. 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 it down. Leave a codebase, tests, and docs that a second and third engineer can pick up quickly. If the business grows, that hire is the next conversation.
- Handle fraud and abuse. Fraud detection, device fingerprinting, and the work that keeps donors and schools safe.
- Watch the cost line. Read cloud and vendor spend, find what is wasted, 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. Availability is yours. 99Pledges earns in short scheduled bursts: a school's walk-a-thon happens on one specific day, usually a weekend, and donations lost to an outage during it do not come back later. You own the alerting that catches problems before organizers do, the response when something breaks at 7am on a Saturday, and 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.
- Shipped LLM features to production. Retrieval, tool use, evals, guardrails. Prototypes do not count.
- A 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. You can tell which debt is costing money and which is just 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 UsYou'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.
