AI & Automations Lead
The AI & Automations Lead at HopSkipDrive is a pivotal role within the IT & Information Security team, focusing on advancing the company's transition to an AI-first organization. This position involves collaborating closely with various departments to integrate AI and automation solutions that enhance operational efficiency and support the company's mission of providing safe, reliable transportation for students. As a remote-first, mission-driven company, HopSkipDrive offers a dynamic environment for professionals passionate about leveraging technology to make a meaningful impact.
In this role, the AI & Automations Lead will be responsible for building and maintaining shared infrastructure, including secure web app hosting and centralized pattern libraries. They will oversee the review and advisory process for all corporate AI and automation builds, ensuring they meet high standards for cost, security, and scalability. Additionally, the lead will partner directly with AI specialists across departments to identify, scope, and develop AI and automation solutions, and will define and maintain the secure intake path for AI and automation requests across the organization. Monitoring and managing AI tool costs will also be a key aspect of the role.
Candidates should have a minimum of five years in technical operations, IT, or support roles, with a strong emphasis on systems integration, automation, and workflow optimization. Practical experience in constructing or managing automation pipelines is essential, including the deployment of large language model (LLM) integrations or advanced AI tools into existing workflows within the past year. Proficiency in building and shipping AI integrations and automation workflows using tools such as n8n, Workato, or Zapier is required, along with comfort in scripting languages like Python or Google Apps Script. Hands-on experience with LLM and agentic systems in a business context, including prompt engineering and fine-tuning, is also necessary.
While specific compensation details are not provided, HopSkipDrive offers a comprehensive benefits package that includes health insurance, paid time off, and opportunities for professional development. The company fosters a collaborative and innovative culture, encouraging team members to contribute ideas and solutions that drive the organization's mission forward. As a rapidly growing company, HopSkipDrive provides ample opportunities for career advancement and the chance to make a significant impact in the field of student transportation.
HopSkipDrive is a technology company dedicated to solving complex transportation challenges with a focus on safety, equity, and care. Founded by three mothers aiming to address their own transportation challenges, the company has grown to facilitate over five million rides across more than 20 states. Recognized for its rapid growth, HopSkipDrive has earned spots on the Inc. 5000 list and the Deloitte 500 Fast-Growing Technology list. The company is a Series D organization with $100 million raised to date, reflecting its strong financial position and commitment to innovation in the transportation sector.