HopSkipDrive

HopSkipDrive

AI & Automations Lead

Remote USA · Full-time

Sponsorship not specified$120k-$145kDetected 16 days ago
PythonGCPCloud PlatformsNLPLLMsAgentic AICommunicationPlain Language

About the role

  • We're the leader in safe, fast, and simple supplemental student transportation.
  • Through our marketplace, we connect kids to highly-vetted caregivers on wheels.
  • Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.

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 that all builders across the organization can pull from.
  • 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.

Requirements

  • You are, first and foremost, a builder.
  • 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 are energized by working across teams and functions.
  • 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.
  • Cross-Functional Influence: The ability to influence without authority across all levels of the organization.
  • You can advise a senior leader, coach a non-technical employee, and earn trust with skeptical peers - without a reporting line to any of them.
  • 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.

Skills

  • About HopSkipDrive
  • 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list.
  • HopSkipDrive is a Series D company and has raised $100M to date.
  • We do, and you will, advance the organization through the following:

Compensation

  • HopSkipDrive is also committed to fair and equitable compensation practices.

Company info

  • 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: 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.
  • 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.
  • Governance & Intake: 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.
  • Tooling Cost Management: Contribute to the organization's AI cost efficiency by monitoring, alerting, and setting thresholds on AI spend across usage-based tools and platforms.
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This listing is sourced directly from HopSkipDrive's careers page and normalized into a canonical job model.