Senior Product Manager - Client Experience

About HopSkipDrive

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

We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. We build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.

The Client Experience team sits at the heart of HopSkipDrive’s RideIQ platform, connecting a powerful product with the wide-ranging needs of school districts, government agencies, and nonprofits. These clients rely on us to deliver safe, reliable, and human-centered transportation for the most vulnerable riders. We’re redefining how institutions manage transportation through intelligent tooling, real-time data, and proactive support. Scaling our efforts means reimagining what's possible. We're leveraging AI to anticipate client needs, streamline operations, and unlock new levels of insight and efficiency, collaborating deeply across the organization to turn big ideas into measurable impact, always grounded in empathy and driven by results.

Who You Are

You are a strategic and customer-obsessed Senior Product Manager with a track record of delivering B2B solutions that drive adoption, satisfaction, and growth. You thrive in real-world complexity, especially when supporting diverse client needs across education, government, and nonprofit sectors.

You are passionate about understanding users deeply, not just their workflows, but their motivations. You translate those insights into intuitive, scalable product experiences. You ask "why" often, combine qualitative and quantitative research, and build for both impact and usability. You bring clarity to ambiguity. You define strong product strategies and lead execution across discovery, delivery, and continuous improvement. You're excited about the potential of AI to reshape client experiences through automation, personalization, and predictive insights. You also know when to apply AI to reduce complexity and when to prioritize human control. You’re a builder, a listener, and a collaborator. You're equally comfortable refining a roadmap, aligning stakeholders, or diving into user research. Most of all, you care about outcomes, not just output.

Specifically, You Bring:

• 5+ years of product management experience, ideally in B2B SaaS, client-facing platforms, or tools serving multiple personas.
• Strong customer empathy, with a proven ability to translate client needs into clear requirements, user stories, and features that drive real-world success.
• Full lifecycle product leadership — from discovery to delivery to iteration — with a focus on product-market fit, usability, and long-term adoption.
• Experience with dashboards, self-service tooling, and workflow platforms that empower operational users and reduce support burden.
• AI curiosity and confidence, with experience exploring or shipping AI-powered features, and a thoughtful approach to when and how to apply AI.
• Data-informed decision making, leveraging research, analytics, and experimentation to guide strategy and evaluate success.
• Product-led growth mindset, able to