Head of Engineering
About This Role
This role reports directly to the executive team and carries complete accountability for engineering outcomes. Core Responsibilities You'll build and lead high-performing engineering and infrastructure teams, ensuring projects deliver on time and to specification. You'll develop technical vision, collaborate with product leadership on elegant solutions, and maintain systems that handle billions of requests. Cost management, operational excellence, and creating an environment where talented engineers thrive all fall within your remit. About You You've led engineering at a meaningful scale — high-traffic systems, large user bases, codebases designed for simplicity and reliability. You're pragmatic about tradeoffs, dig to root causes rather than treating symptoms, and maintain composure under pressure. You take ownership of hard problems and hard conversations. You get stuff done, improve continuously, know your metrics, communicate clearly and precisely, and are not afraid to get your hands dirty. You're a leader in the trenches, not a manager that directs. Technical Environment Rails monolith with Vue.js/TypeScript frontend. Rust for performance-critical services. PostgreSQL, ScyllaDB, Redis, ElasticSearch. Kubernetes orchestration. DataDog, New Relic, Sentry for observability. Terraform for IaC. We believe in well-designed monoliths. We are not pursuing microservices for the sake of it. If DHH's philosophy resonates with you — you'll likely feel at home here. Remote Role Remote team with strong written communication essential. Core hours overlap with both European and North American teams.
Requirements
- Extensive hands-on Ruby on Rails experience — this is a Rails-first environment
- Proven track record leading engineering at scale (3B+ requests/day)
- Strong infrastructure expertise (Kubernetes, Terraform, observability tooling)
- Alignment with monolith-first philosophy — experience breaking down into microservices is not what we need
- Hands-on coding leader who still writes and reviews code daily
- AI-forward mindset — actively uses AI to maximize engineering productivity
- Demonstrated high tenure and commitment — no job hopping
- Exceptional written communication skills for remote collaboration
- Experience building and retaining senior-heavy engineering teams
- Scale-up mentality — gets stuff done, works hard, loves the grind