Job Description
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.
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 8 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. Zen Desk experience preferred
- 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 salary range for this role is $160000 - $180000. 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 one 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**
Skills Required
- Minimum of 8 years of experience in product management
- Experience building and launching LLM-powered agents and conversational AI
- Deep experience in building internal platforms and CRM solutions
- Strong foundation in user experience and human-centric design
- Skill in defining multi-year AI product strategies
- Experience mentoring other product managers
- Highly analytical with data-driven decision making
What the Team is Saying
What We Do
We help get students to their destinations safely and on time. Our technology connects school partners to a network of highly vetted drivers with small vehicles and wheelchair-accessible vehicles complementing the yellow bus filling in gaps and enabling schools to support student transportation needs. 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.
Why Work With Us
HopSkipDrive exists to create opportunity for all through mobility. As the leader in innovative supplemental school transportation we’re taking a different approach to addressing inequities in educational access that are affecting millions of kids each day. We’re paving the way for a future where every student has the chance to succeed.
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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.
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Date Posted
05/27/2026
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