At HopSkipDrive, our goal is to create opportunity for all through mobility.

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Who We Are:

The Operations Excellence team is the engine behind how HopSkipDrive scales its processes, systems, and operational workflows. In 2026, this role is uniquely focused on leading the team through a pivotal transformation: shifting from manual, people-intensive operations to AI-enabled, automated workflows — all while maintaining the safety and compliance rigor our platform demands. You will be responsible for the following:

Lead the AI & Automation transformation, owning the strategic roadmap to move Operations Excellence from manual oversight to intelligent, exception-based processing using Agentic AI workflows, and LLM-integrated tooling.
Manage and develop the Ops Excellence team, including a manager and three direct reports, fostering growth during technical transitions.
Identify, prioritize, and execute automation opportunities across central operations, supply activation, marketplace workflows, and compliance processes — working cross-functionally with Product and Engineering to build and iterate.
Drive measurable improvements in throughput, yield, and cycle time, hitting or exceeding the efficiency benchmarks set for the 2026 fiscal year.
Leverage 2026-standard automation tools (Agentic AI workflows, advanced OCR, automated identity verification, and internal AI orchestration platforms) to evolve process capabilities and eliminate manual friction.
Synthesize complex data insights from our analytics suite to proactively identify and resolve funnel drop-off points, process bottlenecks, and operational risk areas in real-time.
Partner with Product and Engineering to define the technical roadmap for intelligent process automation, including zero-touch onboarding and automated re-certification journeys.
Build the AI/Automation KPI framework, establishing metrics for automation impact — time saved, error reduction, cost efficiency, and team engagement lift.
Manage hybrid workforces, ensuring that onshore teams and offshore partners are up-skilled and effectively utilizing our latest AI orchestration tools.

Who You Are:

You're a strategic leader who thrives on the challenge of evolving operations through cutting-edge technology. You have a proven track record of managing high-volume processes and leading teams through the cultural and operational shifts that automation demands. You bring:

Change Management Leader with experience guiding teams through technical transitions and fostering an "AI-first" mindset across the organization.
Operations Transformation Experience — you've led at least one major shift from manual to automated workflows in a high-growth or technology-driven environment.
Technical Problem-Solver proficient in leveraging modern AI/ML tools, Agentic workflows, and LLM-integrated processing to scale operations.
Data-Driven Strategist who uses advanced visualization and predictive metrics to analyze funnel health and drive continuous improvement.
Strong Cross-Functional Collaborator skilled at partnering with Product and Engineering to build and iterate on internal technical tools.
People-First Manager with 5+ years of management experience, including experience developing mid-level managers. You know how to build trust, address engagement gaps, and develop talent — especially through periods of significant change.
Strategic Project Leader with advanced project management expertise, leveraging ROI-driven analysis to prioritize process intake, optimize resource allocation, and maximize impact.
Results-Oriented Operator with a deep focus on targeted outputs, yield optimization, and reducing cycle times in a high-growth environment.

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 in is 105,000 - 150,000 per year. 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*