Principal Backend Engineer (Ruby on Rails)

About this opportunity The Principal Backend Engineer is the most senior individual contributor on our backend engineering team — the person others go to when a problem is hard, a decision is consequential, or a system needs to be built right the first time. This is not a people-management role, but it is a leadership role: you set the technical direction for our backend systems, raise the engineering bar across teams, and solve problems that cut across products and disciplines. Our backend is built primarily on Ruby on Rails. You’ll own the architecture, standards, and long-term health of those systems while staying hands-on with production code. You’re also an engineer who has figured out how to get great results from AI tooling, and you bring that leverage to everything you do — and help the engineers around you do the same. You’ll report to the SVP of Technology and work closely with product, data, and platform teams. This is a high-ownership role for someone who leads through expertise and trust rather than title. In your first year, you've succeeded when the architecture is documented and actively owned, the backend architecture roadmap is real and being executed, and the engineers around you are making harder technical decisions with more confidence — with or without you in the room. You must reside in one of these US states : AZ, CO, FL, GA, IL, IN, KY, MA, MD, MI, MN, NC, NV, OR, PA, RI, TX, VA, VT, WI, or one of these provinces in Canada: Ontario What you'll do: Own the technical strategy and architecture for our backend systems — making and documenting decisions that affect scalability, reliability, and long-term maintainability, and proactively identifying and addressing architectural risk and technical debt. Lead design reviews for major backend initiatives and capture significant decisions as architecture decision records (ADRs). Define and own the functional discipline roadmap for backend engineering, aligned to the organization-wide roadmap, and partner with Product Leadership to identify and champion cross-cutting strategic initiatives. Define and maintain engineering standards — repository health (documentation, testing, structure), application performance, security, experimentation, and product analytics — publishing them to the engineering playbook. Lead evaluations of third-party engineering tools, making the final call based on technical merit and fit. Write production code on high-complexity, high-impact problems and conduct thorough code reviews that raise the quality of the codebase and the skills of engineers around you. Use AI tooling fluently to accelerate your own work and the team's — not as a novelty, but as a genuine multiplier — and show others how to get strong results from it. Mentor engineers through pairing, design reviews, and feedback, and share knowledge broadly through tech talks and playbook contributions. What you'll need: 8+ years of professional software engineering experience, with demonstrated progression into senior technical leadership. Deep expertise in backend engineering, with strong, current command of Ruby on Rails. Proven experience designing and delivering large-scale, distributed systems that are maintainable, observable, and reliable in production. A strong command of software design principles — SOLID, DRY, domain-driven design, event-driven architecture, and the like. Experience leading technical design across multiple teams or product areas without direct authority. A demonstrated AI-forward practice: you actively use AI tools to get strong results and have a clear point of view on where they help and where they don’t. We’re looking for proven practice and strong fundamentals — not a background building AI/ML systems. Excellent written and verbal communication — you can produce clear architecture docs, decision records, and technical specs, and explain them to engineers and non-engineers alike. Comfort working in a remote, async-first environment with a high degree of ownership and autonomy. Bonus points Experience in a principal, staff, or architect-level role at a product-driven technology company. Familiarity with cloud infrastructure, CI/CD pipelines, and Infrastructure/Platform practices (AWS preferred). Experience with experimentation platforms (Optimizely, LaunchDarkly, VWO, or similar) and product analytics tools (Mixpanel, Amplitude). A background in edtech, SaaS, or consumer-facing digital products. A bachelor’s or advanced degree in Computer Science, Software Engineering, or a related field — though experience speaks louder. A background in or genuine curiosity about the outdoors — our users are hunters, anglers, boaters, and snowmobilers. Competencies Technical Depth & Breadth — Holds deep expertise in backend systems while maintaining enough breadth to reason across the stack and make sound architectural trade-offs. Systems Thinking — Understands how individual technical decisions compound across a codebase, a team, and the business — and designs accordingly. Technical Leadership Without Authority — Influences engineering direction, standards, and culture through expertise and trust, not title or mandate. AI-Forward Practice — Uses AI tooling to accelerate workflow, prototyping, and engineering leverage — and knows how to get reliable results from it rather than treating it as a novelty. Communication & Clarity — Writes and speaks with precision, making complex technical ideas accessible to engineers, product managers, and executives alike. Mentorship & Development — Invests in the growth of the engineers around them and raises the ceiling of what the team can build. Delivery at Scope — Operates strategically without losing the ability to ship; stays hands-on when it matters and delegates when it doesn’t. Judgment Under Ambiguity — Makes sound technical decisions with incomplete information, and knows when to move fast and when to slow down and get it right. What we offer: In addition to a competitive salary and annual bonus, we offer these great benefits: We are a fully distributed company – unless specifically indicated in the job description, this is a work from home position Employer matched 401(k) Medical/Dental/Vision insurance with generous employer contributions (including HSA) Maternity and Paternity leave and benefits Three weeks of paid vacation, 12 paid holidays, a paid community service day, and a flexible work schedule Annual wellness allowance, as well as a paid mental health day once a year for when you need it Automatic WFH contribution to each paycheck Employee Assistance Program (EAP) Kalkomey is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Kalkomey is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email About Kalkomey Kalkomey Enterprises is the trusted guide to outdoor success. Every year, millions of people rely on our platform to gain the knowledge and confidence needed to safely explore the outdoors. Since 1995, Kalkomey has partnered with government agencies across North America to deliver the education that powers responsible outdoor recreation. Our courses and technology platforms support certification programs used by wildlife, parks, and boating agencies while helping outdoor enthusiasts develop the skills needed to safely enjoy activities like hunting, fishing, boating, and snowmobiling. Today, Kalkomey offers more than 360 online learning experiences supported by integrated web and mobile applications. Together, these solutions help make outdoor recreation more accessible, responsible, and safe for generations to come. We believe education builds confidence, and confidence opens the door to the outdoors.