AI & Automations Lead

🕒 June 30

🌵 Arizona, California, +26 more states – Remote

🌵 Arizona – Remote 🏄 California – Remote ⛰️ Colorado – Remote 🦌 Connecticut – Remote 🏛️ District of Columbia – Remote 🐊 Florida – Remote 🌽 Illinois – Remote 🌪️ Kansas – Remote 🎰 Nevada – Remote 🏖️ New Jersey – Remote 🌶️ New Mexico – Remote 🗽 New York – Remote 🌲 North Carolina – Remote 🌪️ Oklahoma – Remote 🌲 Oregon – Remote 🦀 Maryland – Remote 🍂 Massachusetts – Remote 🚗 Michigan – Remote ❄️ Minnesota – Remote 🏰 Missouri – Remote 🔔 Pennsylvania – Remote 🌴 South Carolina – Remote 🎸 Tennessee – Remote 🤠 Texas – Remote ⛷️ Utah – Remote ⚔️ Virginia – Remote ☕ Washington – Remote 🧀 Wisconsin – Remote

💵 $120k - $145k / year

⏰ Full Time

🟠 Senior

🤖 Artificial Intelligence

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HopSkipDrive

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2014

📦 Logistics

💼 Consulting

✈️ Travel

💰 $37M Series D on 2022-09

Logistics • Consulting • Travel

HopSkipDrive is a leading provider of innovative and scalable school transportation solutions, partnering with schools, districts, and counties to provide safe, reliable transportation for youth. They specialize in providing alternatives to traditional school bus routes, catering to students' non-routine needs, those in foster care, and students with special transportation requirements. HopSkipDrive also supports personalized and small group transportation solutions, and uses RouteWise AI technology for transportation optimization. Their service is known for being 40% more affordable than traditional underutilized bus routes. They also address challenges such as bus driver shortages and provide a flexible network of CareDrivers, ensuring safety and reliability.

📋 Description

• 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. • 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 security 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.

🎯 Requirements

• Candidates must possess a minimum of five years in technical operations, IT, or support roles, emphasizing systems integration, automation, and workflow optimization. • 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. • 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. • 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.

🏖️ Benefits

• equity • flexible vacation • medical insurance • dental insurance • vision insurance • life insurance • 401(k) • FSA • opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential.