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 the following:
- 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 spot levers that improve user onboarding, drive engagement, and expand product usage over time.
- Clear product vision and communication, aligning roadmaps with business goals, measurable outcomes, and evolving client needs.
- Collaborative cross-functional skills, especially with engineering, design, ops, and product marketing — ensuring launch success and user impact.
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 base salary range for this role is $160,000 - $175,000. 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 and must be based in 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**
Top Skills
What the Team is Saying
What We Do
We’re a company with heart. Our technology solves complex transportation challenges where there is a heightened need for safety, equity, and care.
Our partnerships with school districts, child welfare agencies and nonprofits ensure equitable educational access for our most vulnerable populations, including youth in foster care, youth experiencing homelessness, and youth with special needs.
We understand that the difference between struggle and success can sometimes be as simple as the ability to show up, which is why we’re on a mission to use innovative technology, coupled with operational expertise and new thinking to help kids reach their full potential by providing a safe, dependable way to get them where they are going.
Why Work With Us
Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than 3.3 million rides and operate across over 13 states across 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.
Gallery
HopSkipDrive Offices
Remote Workspace
Employees work remotely.
HopSkipDrive’s headquarters is located in Los Angeles’ Little Tokyo district and we love this space! However we believe strongly that most roles allow for a remote-first approach to work, and most of our employees work remotely.
