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 is at the intersection of cutting-edge technology and exceptional customer experience. We're a high-impact, collaborative group of product managers, engineers, designers, and operations specialists who build the intelligent systems that power world-class support.

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 goal is to push the boundaries of what’s possible with Generative AI, Conversational AI, and LLM-powered assistance to create seamless, human-centric experiences. Our platforms span the entire support ecosystem, from self-service experience that anticipate customer needs to agent tools that make complex problems feel effortless to solve. Whether it’s voice, chat, workflow automation, or CRM integration, we’re creating the next generation of support technology.

It’s not just about building tools, it’s about fundamentally reimagining how support works. We move fast, think big, and measure our success by how much more effective we make our agents and how much happier we make our customers.

You'll be joining a team that thrives on innovation, values continuous improvement, and believes the best support experiences feel like magic to both customers and agents.