Principal Engineer (Ruby) - REMOTE

I’m not looking for someone who just “does tickets faster.” I’m looking for a CTO‑type Principal who understands technology and business, zooms out to see the system, zooms in to fix the gnarly bits, and constantly applies the business acumen built over a career. Own a core product area and, when needed, lead multi‑team, multi‑product initiatives. Sit on the Architecture Committee, helping define and maintain architectural guidelines for the entire org. Be a co‑owner with the CTO of secure, reliable, and observable systems. Your work will help truly educate today and tomorrow’s students in a revolutionary way. What You’ll Do Own a Product Area and Lead Multi‑Team Initiatives Own the technical direction, quality, and delivery of a key product area within StrongMind. When needed, lead multi‑team, multi‑product projects (cross‑cutting platform changes, shared services, or high‑impact features). Act as the go‑to technical partner for Product Managers in your areas, shaping epics and projects into realistic, incremental slices. Help design and evolve SMC as an online school OS, balancing product needs with platform stability and extensibility. Define and refine service boundaries, module boundaries, data contracts, and integration patterns to keep the cost of future changes low. Sit on the Architecture Committee with the other Principals, helping define and maintain org‑wide architectural guidelines and reviewing major proposals for fit and risk. Make decisions that balance short‑term delivery with 12–24‑month evolution, cutting the right corners without accumulating dangerous debt. Delivery, Economic Thinking & Setting Expectations Own delivery for your product area and for multi‑team initiatives you lead: help scope, slice, sequence, and de‑risk. Be the go‑to person for PMs when work is big, fuzzy, or risky – turning concepts into incremental, shippable plans. Apply heavy economic thinking: constantly weigh effort versus value, short‑term versus long‑term, and help choose the path that maximizes business impact. Help set expectations with leadership and other departments (e.g., “this will slip unless we drop X,” “we should reduce scope here to meet the date,” or “if we invest in this platform piece, shipping features will get cheaper”). Stay Hands‑On Spend meaningful time in the Ruby/Rails codebase, especially on critical paths, refactors and migrations, integrations, and performance work. Model good practices in testing, observability, secure coding, and incremental delivery. Use AI tools to accelerate yourself and others, but keep human judgment and system thinking in the driver’s seat. What Success Looks Like You proactively evolve the tech stack and architecture in your domain and across key initiatives without needing permission, while still hitting delivery commitments. Your product area ships reliably and predictably, and is easier to extend six months from now than it is today. Incidents and production surprises go down, and when they do happen, we learn from them and harden the system. Our testing, observability, and secure development practices are clearly better – and other engineers feel the difference in their day‑to‑day work. SMC is noticeably more of a coherent product and less of an accidental system. Leadership (CTO, VP Eng., CPO, etc.) trusts you to see around corners, provide clear options, and calmly navigate trade‑offs. Nice‑to‑Haves Experience with LLM/AI systems, such as fine‑tuning open‑source LLMs for instructional or educational use, designing RAG‑enhanced LLM flows grounded in internal content, and building action‑based LLM agents that trigger workflows or personalize learning. Deeper experience with observability tooling (Datadog, New Relic, Prometheus, OpenTelemetry). Experience with Kubernetes, Terraform, or Helm. Prior experience in EdTech or integrating with LMS/SIS APIs. Familiarity with compliance/security‑sensitive domains (education, healthcare, finance) even if not K–12‑specific. Benefits Wellness, Your Way – from an on‑site gym and yoga room to flexible work options (select roles). Unplug for the Holidays – a fully paid holiday week off at Christmas. Culture That Celebrates You – champion spotlights, legendary milestone awards at 10, 15, and 20 years, and community service hours that let you give back with heart. Open, Honest & Human – quarterly Town Halls keep our communication transparent and real. Vibes & Good Times – team cookouts, fun treats, and social events that actually make you want to show up. Solid Benefits, Real Support – competitive total compensation package, medical, dental, vision, Unlimited PTO, and voluntary benefits. Additional Info We welcome all qualified candidates eligible to work in the United States. At this time, we are unable to sponsor visas. We are proud to be an Equal Opportunity Employer and provide consideration to all applicants regardless of race, religion, color, sex, gender, national origin, age, veteran status, marital status, or disability protected by law. #J-18808-Ljbffr