AI & Automations Lead

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.

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.

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:

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: