Platform & DevOps Engineer (AI & Testing Infrastructure)

About HopSkipDrive

At HopSkipDrive, our mission is to create opportunity for all through mobility. We’re the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.

Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than five million rides across over 20 states. We continue to grow rapidly—earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.

How We Work

We use AI every day, and not as a productivity add-on. It’s woven into how we work at every level. We’re rethinking how work gets done, who does what, and what a small team can accomplish. If you’ve already built AI into how you work, you’ll hit the ground running. If you haven’t, you’ll need to be ready to learn fast and work differently than you have before.

We’re remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar.

Who We Are

Platform & DevOps is a team that builds the platform that HopSkipDrive Engineering ships on: cloud infrastructure, CI/CD, test infrastructure, and the AI coding-agent tooling used by our product teams. Our engineers use coding agents every day, and this team makes the path from pull request to production as fast and safe as possible.

This Role Will:

• Lead the development of infrastructure to help HopSkipDrive engineers test and ship safely through CI/CD, ephemeral environments, and AI-assisted testing and verification.
• Develop workflows where AI safely drafts test suites, scenarios, and verification artifacts while allowing engineers to oversee quality, evaluations, and safeguards.
• Establish cross-functional benchmarks for defining feature-complete test coverage to evaluate testing practices alongside product teams.
• Instrument time in CI, flake rate, and coverage of critical journeys; report on them and remove the biggest bottlenecks first.
• Provide technical leadership across the platform team and the four product teams, influencing how engineers test and ship without formal authority over them.
• Take part in on-call and incident response for the pipeline and test infrastructure, act as the escalation point when CI or environments fail, and turn incidents into lasting fixes.
• Build alignment in writing with product and engineering through proposals and decision records.

Who You Are

• You are an experienced engineer in developer infrastructure, test automation, or platform engineering, with a record of leading technical work across more than one team and shaping engineering standards through code review and documentation.
• You have strong knowledge of AWS, infrastructure as code (Terraform), containers (Docker or Kubernetes), and Postgres, and are comfortable inside a large Rails application with React and mobile clients.
• You have built and owned a CI/CD pipeline and automated (unit and end-to-end) test coverage that an entire engineering organization depended on.
• You have deep experience with Playwright (or an equivalent), including production experience building systems to run automated tests and CI for web, iOS, and Android.
• You have production experience with coding agents and LLM tooling for test generation or verification, including improving how a team adopts them, and clear views on where they fail.
• You make and explain trade-offs among customer outcomes, delivery speed, technical health, and reliability, in writing, in a remote and asynchronous company.
• You mentor senior and intermediate engineers and raise the bar through others.
• You are direct, low-ego, customer-minded, and human-centric.