Senior Product Manager - AI

Summary

Join HopSkipDrive's Support and Operational Productivity team as a Senior Product Manager, focusing on AI-powered solutions for customer support. You will lead the development of intelligent agents for complex workflows, leveraging AI to improve customer and agent experiences. This role requires extensive experience in product management, AI, enterprise systems, and CRM solutions. You will be responsible for defining multi-year product strategies, mentoring other product managers, and making data-driven decisions. The position offers a competitive salary, equity, flexible vacation, and comprehensive benefits. HopSkipDrive is committed to fair and equitable compensation and is an equal opportunity employer.

Requirements

• 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: 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

Responsibilities

• Lead the development of intelligent agents that understand, decide, and act across complex enterprise and customer service workflows
• Define multi-year AI product strategies
• Translate ambiguous problems into clear roadmaps and drive execution from ideation to growth
• Mentor other product managers on AI development, compliance, and platform scalability
• Foster a culture of curiosity and learning
• Leverage data and user research to inform product decisions, optimize experiences, and measure impact

Benefits

• Every full-time employee has equity
• Flexible vacation
• Medical, dental, vision and life insurance
• 401(k)
• FSA
• Opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential