Senior Product Manager - AI

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: 

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. 

Who You Are:

You are an experienced and empathetic Senior Product Manager who thrives at the intersection of AI innovation and real-world user problems. You are a product leader with a proven ability to build intelligent agents that understand, decide, and act across complex enterprise and customer service workflows.

• Minimum of 5 years of experience in product management, with a focus on customer support, platform, or internal tools, or mission-critical systems where reliability and user experience are non-negotiable. 
• AI-first leadership: You lead with AI as the default solution, with proven experience building and launching LLM-powered agents, conversational AI, and AI-native experiences that transform how work gets done and how support is delivered.
• Enterprise systems and CRM expertise: Deep experience building internal platforms, CRM solutions, and organization toolings that enable cross-functional teams, streamline operations, and scale business processes across complex organizations.
• Human-Centric Design: A strong foundation in user experience, with a passion for designing technology that feels intuitive, human, and reduces friction for real people.
• Strategic Vision & Execution: Skill in defining multi-year AI product strategies, translating ambiguous problems into clear roadmaps, and driving execution from ideation to growth.
• Mentorship & Influence: Experience mentoring other product managers on AI development, compliance, and platform scalability, fostering a culture of curiosity and learning.
• Data-Driven Decision Making: Highly analytical, leveraging data and user research to inform product decisions, optimize experiences, and measure 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 - $190,000. 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, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OH, OK, OR, SC, TN, TX, UT, VA, WA, WI**