Monolith Productions Jobs (NOW HIRING)

CTO's Note About This Role
I'm not looking for someone who just "does tickets faster."
I'm looking for a CTO-type Principal - someone who understands technology and business, who can zoom out to see the system, zoom in to fix the gnarly bits, and constantly apply the business acumen you've built over your career.
You'll:
- Own a core product area and, when needed, lead multi-team, multi-product initiatives.
- Sit on our Architecture Committee, helping define and maintain the architectural guidelines for the entire org.
- Be a co-owner with me of secure, reliable, and observable systems
- Your work will help truly educate today and tomorrow's students in a revolutionary way!
I want someone who is independent but aligned: you don't wait for permission to evolve the stack, but you keep your promises, hit your dates and if you can't, you come up with solutions, trade-offs, plans and designs to achieve the goals one way or another.
If you like being the person leadership comes to when things are fuzzy, risky, or complex - and you enjoy turning that fuzz into clear options, trade-offs, and plans - you'll be very happy here.
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 (for example, 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.
Architecture, Systems Design
- 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 (for example, "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.
Must-Have Skills & Experience
- Expert professional software engineering experience.
- You built real products at scale with Ruby on Rails.
- Mastery-level Ruby/Rails, including deep understanding of Rails internals and ecosystem, ActiveRecord, background jobs, caching, performance tuning, and secure coding practices.
- Strong full-stack skills, including HTML/CSS/JavaScript plus at least one modern front-end framework (for example, React, Vue, Stimulus, or similar).
- Solid API and integration experience, including designing and evolving RESTful APIs;
- Strong relational database skills: schema design, indexing, query optimization, and migrations at scale (PostgreSQL or similar).
- Proven experience designing and evolving complex systems (monolith, modular monolith, or service-oriented architectures) in production.
- Experience with cloud and DevOps basics, including deploying and operating apps on AWS/GCP/Azure, CI/CD pipelines, and containerization (Docker).
- Excellent communication in a remote environment: clear writing, clear trade-offs
- Demonstrated ability to mentor other engineers and influence across multiple teams.
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 (for example, 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.
Perks, Benefits & Culture You'll Love:
Wellness, Your WayFrom an on-site gym and yoga room to flexible work options (select roles), we believe your well-being fuels your brilliance.
Unplug for the HolidaysA fully paid holiday week off at Christmas-because rest isn't a luxury, it's essential.
Culture That Celebrates YouChampion spotlights, legendary milestone awards at 10, 15, and 20 years, and community service hours that let you give back with heart.
Open, Honest & HumanQuarterly Town Halls keep our communication transparent-and real.
Vibes & Good TimesThink team cookouts, fun treats, and social events that actually make you want to show up.
Solid Benefits, Real Support
At StrongMind, we offer a competitive total compensation package, informed by market data and aligned with our size, stage, industry, and location. Medical, dental, vision, Unlimited PTO, and voluntary benefits-we take care of the people who make the magic happen.
Your Voice MattersWe're constantly evolving, and that includes how we support, celebrate, and invest in our people.
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.
Environmental Conditions: Collaborative open environment, office environment
Equal Opportunity Employer
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