Senior Product Manager, HopSkipDrive
Artificial Intelligence
$160-190k
+ Equity
More information about location
Safe youth transportation solution
Job no longer available
Safe youth transportation solution
501-1000 employees
Job no longer available
$160-190k
+ Equity
More information about location
501-1000 employees
Company mission
To create opportunity for all through mobility.
Role
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
What the job involves
- 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 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
- 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
Our take
Across the US, school transportation is under pressure as driver shortages, budget cuts, and rigid bus routes are making it harder for students to get to school safely and on time. This has opened the door for smaller vehicles and ride-hailing services to step in and support those students who don't fit neatly into traditional routes. HopSkipDrive has grown within this space, offering a flexible alternative that helps schools fill these gaps.
HopSkipDrive connects children with carefully vetted caregivers (often grandparents, nurses or childcare professionals) who then provide reliable rides when buses or public transport fall short. Operating in 21 states and supporting over 13,000 schools, the service has certainly eased commutes for many families.
And now the company is focused on strengthening its impact with technology and innovation. With its RouteWise AI platform, it helps districts cut costs, improve efficiency and manage driver shortages, all while new safety modules and AI-driven planning tools continue to raise industry standards. With these advancements and a growing network of partners, the company is ready to keep shaping a more flexible future for school transportation.
Freddie
Company Specialist at Welcome to the Jungle
Insights
23% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Sep 2022
$37m
SERIES D
Aug 2021
$25m
SERIES C
Total funding: $107m
Company benefits
- Medical, Dental & Vision
- Health Spending Account
- Mental Health Resources
- Employee Assistance Program
- Short- & Long-Term Disability Insurance
- Paid Parental Leave
- 401K Plan
- Company Ownership/Equity
- Medical & Dependent Care FSA
- Travel Insurance
- Supplemental Legal
- Fully Remote Work Option
- Flexible Time Off
- 11 Annual Paid Holidays
- Week Closure at End of Year
- Sick Time Off for You and Family
- Home Internet Reimbursement
- Professional Development & Learning Stipend
- Remote & In-Person Quarterly Team Events
- Internal Rewards & Recognition Program
- Employee Referral Bonuses
Company HQ
Little Tokyo, Los Angeles, CA
Leadership
Joanna McFarland
(Co-Founder & CEO)Former Board Member at the Marketplace Industry Association and LA Tech.org.
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