HopSkipDrive
HopSkipDrive

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About HopSkipDrive At HopSkipDrive, our mission is to create opportunity for all through mobility ... Build and maintain shared infrastructure: secure web app hosting infrastructure, MCP/API standards ...

$100/day

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 10 days ago


Job description

About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. 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.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly - earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who We Are
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.
  • 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.

Who You Are
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 also understand that in an organization handling children's data and real-time mobility, how you build matters as much as what you build. Security awareness is baked into how you think.
You are energized by working across teams and functions. You do not need formal authority to move things forward. You build trust by showing up with good ideas, clear reasoning, and the ability to translate between technical and business partners. 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.
Skills and Experience:
  • Experience: Candidates must possess a minimum of five years in technical operations, IT, or support roles, emphasizing systems integration, automation, and workflow optimization. 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.
  • AI & Automation Building: 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.
  • LLM & Agentic Systems: 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.
  • Cloud & Infrastructure: Familiarity with cloud infrastructure, particularly GCP, including secrets management, IAM fundamentals, and secure-by-default hosting patterns. You do not need to be a cloud architect, but you need to know enough to build responsibly.
  • 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.
  • Risk Communication: 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.

Our Investment In You
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is $120,000 - $145,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate's relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
* This role will be fully remote in one of the following states AZ, CA, CO, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI, PA**

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About HopSkipDrive

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HopSkipDrive 's m ission is to create opportunity for all through mobility. Our safe, innovative youth transportation solution is used by over 300 school districts, charter schools, government agencies and busy families to get kids where they need to go. With nearly 500,000 yellow buses on the road every day and 3.5 billion miles driven a year, student transportation is the largest mass transit system in the US. And while districts spend $25 billion annually on transportation, only 30% of kids get to school everyday on a school bus. Add to the equation a crippling bus driver shortage and increasing needs for individualized transportation solutions, and it is clear the current system is expensive, inefficient and ripe for disruption. We create personalized transportation solutions from one to many, and everything in between. We're a company with heart Our partnerships with school districts, child welfare agencies and nonprofits ensure equitable educational access for our most vulnerable populations, including youth in foster care, youth experiencing homelessness, and youth with special needs. We understand that the difference between struggle and success can sometimes be as simple as the ability to show up, which is why we're on a mission to use innovative technology, coupled with operational expertise and new thinking to help kids reach their full potential by providing a safe, dependable way to get them where they are going. We're an awesome place to work Our company culture has been well-recognized - HopSkipDrive has been named to Best Places to Work lists from Built in LA, Comparably, Inc. and the Los Angeles Business Journal. Comparably also named us to the Best Company for Professional Development, Best CEO and Best CEOs for Women lists. We're growing rapidly Founded by three moms as a solution to their own transportation challenges, we now serve nine states and 16 markets across the country and continue to expand at a rapid pace, twice making the Inc. 5000 and Deloitte 500 Fast-Growing Technology lists. Backed by top-tier venture capital firms, HopSkipDrive has raised $70M in funding to date.

Industry

It services

Company size

11 - 50 Employees

Headquarters location

Los Angeles, CA, US

Year founded

2014