People Generalist

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.

This role sits at the heart of the People & Talent team — the connective tissue between our People Business Partners, People Operations, and Talent. You'll operate across all three, which means you're the person who sees the full picture: a lifecycle change that needs a business partner's judgment call, a program that needs an operations fix, a req that needs talent's eye. As HopSkipDrive scales and our People programs mature — from performance calibration to onboarding to compliance — we need someone who can own that connective work so the rest of the team can stay focused on strategy, operational excellence, and the business partnerships that move the needle.

We expect you to come in and use AI to streamline the recurring, repeatable parts of the job — the process should never be manual just because it's always been manual. But just as important, we expect you to know where AI stops and human judgment starts.

What You’ll Do

Onboarding and lifecycle operations

• Own the onboarding experience end to end, ensuring every new hire has a welcoming, organized, and consistent start.
• Partner with IT, Payroll, and hiring managers to make sure onboarding activities are completed accurately and on time.
• Manage employee lifecycle changes — promotions, transfers, manager changes, employment-status changes, and departures — with the accuracy this data deserves given how it feeds comp, performance, and reporting downstream.
• Maintain accurate employee records across our People systems (ChartHop, ADP, Leapsome) and ensure changes are properly documented.
• Identify inefficiencies and independently propose scalable, AI-enabled solutions to automate or streamline recurring lifecycle processes, partnering with cross functional partners to implement and/or approve said processes

Supporting People Programs

• Help coordinate and administer company-wide People programs, including surveys, learning & development initiatives, and engagement, wellness & recognition programs.
• Develop program materials, employee communications, manager resources, timelines, and process documentation that hold up under real manager use.
• Gather and organize employee feedback, program data, and operational insights to help the team evaluate what's working.
• Partner with People & Talent teammates on the continuous improvement of employee programs, including our current performance calibration and manager-accountability work.

People Business Partner Support

• Track policy rollouts, handbook acknowledgments, and compliance postings across our multi-state footprint.
• Facilitate leaves of absence and workplace accommodation processes in partnership with employees, managers, benefits providers, and other stakeholders.
• Guide employees through leave requirements, documentation, timelines, pay coordination, and return-to-work processes with discretion and empathy.

Talent

• Jump in to drive full-cycle hiring when needed by sourcing talent, scheduling interviews, and partnering directly with hiring managers to fill operational roles.

What You’ll Bring

• 3+ years of experience in People Operations/HR.
• Solid understanding of the employee lifecycle end to end.
• Experience coordinating onboarding, leaves of absence, employee relations, talent, and other employee-facing programs.
• Excellent written and verbal communication skills, including the ability to explain complex processes clearly and empathetically.
• Sound judgment and the instinct to know when an issue needs to be escalated — you won't sit on something that matters.
• High attention to detail and a real commitment to accurate records — this data drives comp, performance, and compliance decisions.
• Demonstrated discretion handling sensitive and confidential employee information.
• Comfort working in a fast-moving environment where processes are still evolving — you're energized by building the plane while flying it, not frustrated by it.
• A collaborative, service-oriented approach and the ability to build trusted relationships with employees, managers, and cross-functional partners.
• Comfort using AI tools to build efficiency into recurring People work — we're an AI-forward team and expect every hire to meet at least an “experimenting” bar.
• Experience working with ADP WorkforceNow, Greenhouse, and other people & talent platforms.

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 $80,000 - $90,000. 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, 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*

We are not currently considering candidates who will perform work from any other state.