Lead Engineer - Ruby on Rails

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

About 99Pledges:

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 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 Us:

You’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.

Our Values at Beacon Software

• Humility: We acknowledge that the path to getting to the right answer involves being wrong along the way. We have strong beliefs which are weakly held. We actively seek new ideas and believe we can learn from anyone at any time.
• Honesty: We are truth seeking in our approach to business problems. Business is a repeat game and we believe that human relationships generate alpha. We understand that trust is earned over a lifetime and can be lost in an instant.
• Hunger: We play to win. We hold ourselves to high standards and will not be outworked. We take pride in having a deep sense of responsibility to ourselves, each other, our partners, and our customers. We believe to whom much is given much is expected.
• Horizon: We seek to build a generational software company. This will take decades. We manage our expectations and those of our partners to take advantage of the 8th wonder of the world - compounding growth.

How We Use AI in Our Hiring Process:

How We Use AI in Our Hiring Process: To ensure transparency, we want candidates to know that Beacon Software uses Artificial Intelligence and AI-enabled tools to assist with screening, reviewing, organizing and highlighting profiles and applications that match the key requirements for each role.

AI does not make hiring decisions:

AI does not make hiring decisions: Every application is reviewed by a member of our team, and all decisions throughout the process are made by humans. We use AI to support efficiency and consistency, not to replace human judgment. We are committed to a fair, thoughtful, and equitable experience for every candidate.