AI & Automations Lead

About this role

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.

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. We do, and you will, advance the organization through the following:

• 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 security 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.

You are energized by working across teams and functions. You do not need formal authority to move things forward. You build trust by showing up with good ideas, clear reasoning, and the ability to translate between technical and business partners. When a department leader wants to ship an AI workflow that is not ready, you can say so in a way that keeps the relationship intact and still gets the work done right.

Skills and Experience:

• Experience: Candidates must possess a minimum of five years in technical operations, IT, or support roles, emphasizing systems integration, automation, and workflow optimization. Crucially, applicants must have practical expertise in constructing or managing automation pipelines. Within the past year, this experience should include the deployment of LLM integrations or advanced AI tools into existing workflows.

• AI & Automation Building: Proven track record building and shipping AI integrations and automation workflows using tools such as n8n, Workato, Zapier, or comparable platforms, with comfort in Python, Google Apps Script, or similar scripting languages.

• LLM & Agentic Systems: Hands-on experience with large language model tools in a business context — prompt engineering, agent design, Claude Skills, MCP servers, or API integrations — and a practical understanding of where these systems can go wrong, including prompt injection, data exposure, and over-scoped access.

• Cloud & Infrastructure: Familiarity with cloud…