AI & Automations Lead

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're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward.

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

Our IT & Information Security team is at the forefront of HopSkipDrive's transition to an AI-first organization. We are not a traditional IT department. We are an enterprise enablement team closely partnered with the business sitting at the intersection of children's safety, regulated education data, and real-time mobility. We are leveraging the latest technologies and tools to build a world-class AI-enabled company, and doing it at a pace that matches the ambition. We operate secure-by-default, and we look for people who take the responsibilities of security, reliability, and scalability seriously while moving fast to create real change.

• Shared Infrastructure & Guardrails: Build and maintain shared infrastructure: secure web app hosting infrastructure, MCP/API standards, secret/key management, model selection, guardrails, and a centralized pattern library that all builders across the organization can pull from.
• AI & Automation Enablement and Advisory: Own the review, tracking, and advisory process for all corporate AI and automation builds — MCP servers and tool configurations, Claude Skills, API integrations, and agentic workflows — before deployment.
• Forward-Deployed Building: Partner directly with AI specialists across departments to identify, scope, and build AI and automation solutions that meet high standards for cost, security, and scalability before they ship.
• Governance & Intake: Define and maintain the secure intake path for AI and automation requests across the organization, replacing ad-hoc builds and shadow IT with a governed, cost effective, and scalable process.
• Tooling Cost Management: Contribute to the organization's AI cost efficiency by monitoring, alerting, and setting thresholds on AI spend across usage-based tools and platforms.

Who You Are

You are, first and foremost, a builder. You have spent your career shipping solutions that work in production, and you take real satisfaction in getting something from idea to deployed and running. You also understand that in an organization handling children's data and real-time mobility, how you build matters as much as what you build. Security awareness is baked into how you think.