The posting
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 over 20states. 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 and grow a team of Platform and DevOps engineers. Set direction, coach, hire, and stay hands-on for part of your week.
- Own our AWS platform end-to-end: infrastructure as code, Kubernetes, CI/CD, environments, observability, incident response, and cloud cost.
- Lead the practice of Agentic Software Development Lifecycle (ASDLC) to ensure these AI tools remain safe, aligned, and continuously improving.
- Make automated verification standard by enabling product teams to release with embedded tests across web and mobile.
- Deliver deployment environments and CI pipelines that keep pace with agent-generated change.
- Measure and improve system delivery, including baseline time in CI, code review, and QA.
- Build alignment in writing with product and engineering leaders on platform roadmap and investment trade-offs.
Who You Are
- You are a hands-on Platform or DevOps engineer who has stepped into leadership. You have managed engineers and still find time to ship. You have run a team through real on-call and incident response, platform growth, and AI/agentic transformation.
- You have deep knowledge in AWS, infrastructure as code (Terraform), Kubernetes, and Postgres, with production experience operating a large web and mobile application surface area.
- You have experience putting coding agents and LLM tooling to work in a real software lifecycle: CI integration, evaluation, guardrails, and cost control. You have improved how an engineering org adopts them.
- You have a grounded view on CI/CD, know what a regression suite platform should cover, how to keep it fast and trusted, and how to help engineers move from manual to automated testing.
- You are fluent in delivery and reliability metrics and able to use them to coach a team rather than rank people.
- You are a clear writer who builds alignment through proposals and decision records in a remote and asynchronous company.
- You are curious and experimental with new tools, with a track record of independently adopting generative AI to accelerate your own work and your team's.
- You are direct, low-ego, customer-minded, and human-centric.
Our Investment In You
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is $180,000.00 - $205.000.00. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
"This is a fully remote role. Candidates must reside in and perform work from one of the following states: AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, or WI. We are not currently considering candidates who will perform work from any other state."
