AI & Automations Lead

Role Description

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.

• 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.
• Partner directly with AI specialists across departments to identify, scope, and build AI and automation solutions.
• Define and maintain the secure intake path for AI and automation requests across the organization.
• Contribute to the organization’s AI cost efficiency by monitoring, alerting, and setting thresholds on AI spend.

Qualifications

• 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, including deployment of LLM integrations or advanced AI tools.
• Proven track record building and shipping AI integrations and automation workflows using tools such as n8n, Workato, Zapier, or comparable platforms.
• Hands-on experience with large language model tools in a business context.
• Familiarity with cloud infrastructure, particularly GCP, including secrets management and IAM fundamentals.
• The ability to influence without authority across all levels of the organization.
• Clear, structured communication when it comes to risk.

Requirements

• Security awareness is baked into how you think.
• Ability to build trust by showing up with good ideas, clear reasoning, and the ability to translate between technical and business partners.
• Ability to communicate effectively with department leaders and maintain relationships while ensuring quality work.

Benefits

• Equity for every full-time employee.
• Flexible vacation.
• Medical, dental, vision, and life insurance.
• 401(k) and FSA.
• Opportunity to work for a uniquely positioned, VC-backed company.
• Salary range: $120,000 - $145,000, determined by relevant work experience, skill set, certifications, and specific work location.
• Total compensation package includes equity stock options.

Company Description

HopSkipDrive is a leader in safe, fast, and simple supplemental student transportation. Founded by three moms, we've facilitated more than five million rides across over 20 states. We continue to grow rapidly, earning spots on the Inc. 5000 list and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.