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Salary: USD 180,000 - 205,000 / annual
HopSkipDrive is a Series D marketplace and software platform connecting students with vetted caregivers for supplemental transportation. The company has facilitated over five million rides across 20+ states and is on the Inc. 5000 and Deloitte 500 Fast-Growing Technology lists. The company is remote-first and deeply integrated AI into its engineering operations.
The Platform & DevOps team builds the infrastructure and tooling that enables HopSkipDrive's engineering organization to ship reliably and rapidly. This includes cloud infrastructure, CI/CD pipelines, test infrastructure, and AI coding-agent tooling used by product teams.
As Engineering Manager, Platform & DevOps, you will lead and grow a team of platform and DevOps engineers while remaining hands-on for part of your week. You will own the AWS platform end-to-end, including infrastructure as code, Kubernetes, CI/CD, environments, observability, incident response, and cloud cost optimization. You will lead the practice of Agentic Software Development Lifecycle (ASDLC) to ensure AI tools remain safe, aligned, and continuously improving. Key responsibilities include enabling product teams to release with embedded tests across web and mobile, delivering deployment environments and CI pipelines that keep pace with agent-generated change, measuring and improving system delivery metrics (CI time, code review, QA), and building alignment with product and engineering leaders on platform roadmap and investment trade-offs through clear written communication.
You will set direction for the team, coach engineers, hire, and stay involved in technical execution. The role requires managing engineers through real on-call and incident response scenarios, platform growth initiatives, and AI/agentic transformation efforts.
REQUIREMENTS:
- Hands-on Platform or DevOps engineer with proven team leadership experience; must have managed engineers while continuing to ship code
- Deep production knowledge of AWS, infrastructure as code (Terraform), Kubernetes, and Postgres, with experience operating large web and mobile application surfaces
- Demonstrated experience integrating coding agents and LLM tooling into real software lifecycles: CI integration, evaluation, guardrails, and cost control; track record of improving how engineering orgs adopt these tools
- Strong understanding of CI/CD best practices, regression suite design, test automation, and helping teams transition from manual to automated testing
- Fluency in delivery and reliability metrics; ability to use metrics for coaching rather than ranking
- Excellent written communication skills; ability to build alignment through proposals and decision records in remote, asynchronous environments
- Curiosity and hands-on experience with generative AI tools; track record of independently adopting AI to accelerate personal and team work
- Direct, low-ego, customer-minded, and human-centric approach
