AI & Automations Lead

HopSkipDrive

2d•$120,000 - $145,000•Remote

About The Position

HopSkipDrive is seeking an AI & Automations Lead to join their IT & Information Security team. This role is crucial in transitioning the company to an AI-first organization, focusing on enterprise enablement and leveraging the latest technologies. The team operates at the intersection of children's safety, regulated education data, and real-time mobility, building a world-class AI-enabled company with a secure-by-default approach. Responsibilities include building and maintaining shared infrastructure, providing AI and automation enablement and advisory, forward-deployed building in partnership with AI specialists, defining and maintaining a secure governance and intake process for AI/automation requests, and managing tooling costs for AI efficiency.

Requirements

Minimum of five years in technical operations, IT, or support roles, emphasizing systems integration, automation, and workflow optimization.
Practical expertise in constructing or managing automation pipelines.
Within the past year, experience should include the deployment of LLM integrations or advanced AI tools into existing workflows.
Proven track record building and shipping AI integrations and automation workflows using tools such as n8n, Workato, Zapier, or comparable platforms.
Comfort in Python, Google Apps Script, or similar scripting languages.
Hands-on experience with large language model tools in a business context — prompt engineering, agent design, Claude Skills, MCP servers, or API integrations.
Practical understanding of where these systems can go wrong, including prompt injection, data exposure, and over-scoped access.
Familiarity with cloud infrastructure, particularly GCP, including secrets management, IAM fundamentals, and secure-by-default hosting patterns.
The ability to influence without authority across all levels of the organization.
Clear, structured communication when it comes to risk. You can write a concise review, explain a guardrail in plain language, and escalate a finding to the right person without over-engineering the message.

Responsibilities

Build and maintain shared infrastructure: secure web app hosting infrastructure, MCP/API standards, secret/key management, model selection, guardrails, and a centralized pattern library.
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.
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.
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.
Contribute to the organization’s AI cost efficiency by monitoring, alerting, and setting thresholds on AI spend across usage-based tools and platforms.