Senior Product Manager, Ops & Customer Experience

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 20 states. 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're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward. We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar. 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 t