[Hiring] Senior Manager, DevOps @HopSkipDrive

Role Description

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.

Qualifications

• 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 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.

Requirements

• Experience in leading a team of engineers.
• Proficiency in AWS, Terraform, Kubernetes, and Postgres.
• Hands-on experience with coding agents and LLM tooling.
• Strong understanding of CI/CD processes.
• Ability to analyze delivery and reliability metrics.
• Excellent written communication skills.
• Curiosity and willingness to experiment with new tools.

Benefits

• Equity for every full-time employee.
• Flexible vacation policy.
• Medical, dental, vision, and life insurance.
• 401(k) and FSA options.
• Opportunity to work for a uniquely positioned, VC-backed company.
• Significant upside potential in a rapidly growing space.

Company Description

HopSkipDrive is a leader in safe, fast, and simple supplemental student transportation, connecting kids to highly-vetted caregivers on wheels. Founded by three moms, we have facilitated more than five million rides across over 20 states and continue to grow rapidly.