Lead Engineer – Ruby on Rails

This is a fully remote position, open to applicants in United States.

📋 Description

• Collaborate with the GM, product team, and customers to establish the engineering and product roadmap.

• Convert business priorities into a structured plan while articulating tradeoffs.

• Oversee donations, automatic payouts, and reconciliation across various payment providers.

• Manage retries, idempotency, webhooks, and address issues with degraded payment providers during campaigns.

• Implement AI features in production, ensuring evaluations, guardrails, and tenant-safe tool usage are in place.

• Utilize coding agents to enhance individual engineering productivity.

• Elevate engineering standards through trunk-based development, continuous integration (CI), staging with synthetic data, feature flags, test coverage, and dependable deployments.

• Document the codebase, testing procedures, and processes for the benefit of future engineers.

• Address fraud detection, device fingerprinting, and ensure the safety of donors and schools.

• Monitor cloud and vendor expenditures, optimizing costs effectively.

• Engage directly with operators, school administrators, and partners.

• Take ownership of alerting, uptime, incident response, and subsequent remediation for scheduled fundraising events.

⛳️ Requirements

• Senior generalist capable of operating across web, data, infrastructure, and AI, with a quick adaptability to unfamiliar technology stacks.

• Experience in production environments managing financial transactions, including payment integrations, payouts, reconciliation, or fraud prevention efforts.

• Proven experience as the sole engineer or primary technical owner of a significant system, covering design, build, deployment, on-call responsibilities, and customer support during incidents.

• Proficient in modeling, querying, and optimizing production PostgreSQL databases.

• Familiarity with running migrations on large tables without experiencing downtime.

• Experience deploying LLM features to production, encompassing retrieval, tool utilization, evaluations, and guardrails.

• A history of implementing trunk-based development, automated testing, and maintaining discipline in environments while consistently delivering results.

• Strong judgment regarding technical debt and its implications on business costs.

• Exceptional writing skills.

• Proficiency in Ruby on Rails 7 and Ruby 3.1.

• Experience with PostgreSQL, HAML, SCSS, Bootstrap, jQuery, Delayed Job, Braintree, PayPal, Dwolla, Stripe, Heroku, AWS S3, Redis, Postmark, Honeybadger, New Relic, Datadog, and PostHog.

• Capability to incorporate coding agents into daily work routines.

🏝️ Benefits

• Contribute to software that empowers organizations to raise funds for meaningful causes.

• Experience a direct and noticeable impact on the product and the communities it serves.

• Work within a small team environment.

• Benefit from an AI-assisted hiring process, ensuring that every application is reviewed by a human.