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 Support and Operational Productivity team sits at the intersection of customer experience, operational excellence, and business growth. We're a high-impact, collaborative group of product managers, engineers, designers, and operations specialists who build the systems and experiences that keep HopSkipDrive running — for our customers and for the teams that serve them.

Our support world is uniquely complex. We serve schools and parents coordinating their children’s transportation, school administrators managing district-wide logistics, drivers navigating complex pickup instructions and multi-stop coordination, and the operations team orchestrating it all. Every interaction involves multiple stakeholders, tight safety requirements, and real-time coordination.

Our work spans the full operational landscape of HopSkipDrive — from the customer-facing experiences that keep riders, CareDrivers, caregivers, and school partners informed and supported, to the internal platforms that power how our teams operate across support, sales, revenue operations, and safety. We think deeply about the people on both sides of every interaction: the customer navigating a problem, and the team member solving it. That dual lens — user experience and operational excellence, together — is what makes this work uniquely challenging and uniquely impactful.

We move fast, think big, and measure success by how much more effective we make our teams and how much better we serve our customers.

Who You Are

You are a seasoned, versatile Senior Product Manager who leads with curiosity and conviction. You don't just build features — you develop a deep understanding of your customers, your business, and your stakeholders, and use that understanding to make smart bets and drive real outcomes. You're as comfortable in a strategic planning session as you are in a sprint review, and you have a track record of bringing people together around a shared vision.

• Minimum of 8 years of experience in product management, ideally spanning customer-facing platforms, operational tooling, or internal systems in complex, multi-stakeholder environments where reliability and user experience are non-negotiable.
• Strong Customer Instincts: a proven ability to build genuine, nuanced understanding of users through research and data, and to translate those insights into product decisions that matter
• Strategic Vision & Execution: You think in systems and over horizons. Skilled at defining multi-year product strategies, cutting through ambiguity to set clear direction, and driving execution from ideation through growth. You can zoom out to shape a roadmap and zoom in to unblock a team — and you know when to do each.
• Cross-Functional Collaboration: A proven partner to teams across the organization. You navigate competing priorities, broker alignment, and build the kind of collaborative relationships that make hard things possible. You understand that great product work happens at the intersection of functions, not in silos.
• Platform & Systems Thinking: Comfortable building internal platforms, CRM solutions, and operational tooling that scales business processes and enables cross-functional teams. You think holistically about how systems interact and how tooling choices shape team performance and customer experience.
• Data-Driven Decision Making: Highly analytical. You leverage data, customer research, and operational metrics to inform product decisions, evaluate tradeoffs, and measure impact — and you foster that same orientation in the teams and stakeholders around you.

Preferred experience that will set you up for success from day one:

• Hands-on experience with customer support or helpdesk platforms such as Zendesk, Salesforce Service Cloud, or Intercom. Understanding how agents work, not just how the tools are configured
• Familiarity with CRM systems and how they connect customer data, workflows, and team operations at scale
• Experience building with or alongside generative AI tools, whether LLM-powered features, AI agents, or conversational experiences, with a practical understanding of where they work well and where they don't
• Experience building internal tools or operational platforms that meaningfully changed how a team works
• Background in industries where safety, trust, or care are central to the product — transportation, logistics, healthcare, childcare, or similar

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 committed to fair and equitable compensation practices. The salary range for this role is $160,000 - $180,000. 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 is a fully remote role. Candidates must reside in and perform work from 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, or WI. We are not currently considering candidates who will perform work from any other state.