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Salary: USD 195,000 - 210,000 / annual
HopSkipDrive is a Series D marketplace platform connecting students with vetted caregivers for supplemental transportation, operating across 20+ states and having facilitated over 5 million rides. The company is Series D-funded with $100M raised and is recognized on the Inc. 5000 and Deloitte 500 Fast-Growing Technology lists.
The Platform & DevOps team builds the infrastructure that enables HopSkipDrive's engineering organization to ship safely and quickly. This includes cloud infrastructure, CI/CD pipelines, test infrastructure, and AI coding-agent tooling used by product teams. The team operates in a remote-first, AI-integrated environment where coding agents are used daily to accelerate development.
In this Staff-level role, you will lead the development of quality and test infrastructure that helps engineers test and ship safely. Key responsibilities include:
- Leading development of CI/CD, ephemeral environments, and AI-assisted testing and verification infrastructure
- Designing workflows where AI safely drafts test suites and verification artifacts while engineers maintain oversight and control
- Establishing cross-functional benchmarks for test coverage with product teams
- Instrumenting and optimizing CI metrics (time, flake rate, coverage) and removing bottlenecks
- Providing technical leadership across the platform team and four product teams through influence and mentorship rather than formal authority
- Participating in on-call and incident response for pipeline and test infrastructure, serving as escalation point for CI/environment failures
- Building alignment through written proposals and decision records in an asynchronous environment
You will mentor senior and intermediate engineers, raise the bar through others, and make trade-offs among customer outcomes, delivery speed, technical health, and reliability.
REQUIREMENTS:
- Extensive experience in developer infrastructure, test automation, or platform engineering with a track record of leading technical work across multiple teams and shaping engineering standards
- Strong knowledge of AWS, infrastructure as code (Terraform), containers (Docker/Kubernetes), and Postgres
- Comfort working inside large Rails applications with React and mobile clients
- Proven ownership of CI/CD pipelines and automated test coverage (unit and end-to-end) that an entire engineering organization depended on
- Deep production experience with Playwright or equivalent, including building systems to run automated tests and CI for web, iOS, and Android
- Production experience with coding agents and LLM tooling for test generation or verification, including team adoption and clear understanding of limitations
- Ability to make and explain trade-offs in writing in a remote, asynchronous environment
- Experience mentoring senior and intermediate engineers
- Direct, low-ego, customer-minded, and human-centric approach
