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
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