Senior Product Manager, Ops & Customer Experience

About the role

You own the end-to-end product strategy and roadmap for the Support and Operational Productivity domain at HopSkipDrive, defining how we solve the most complex operational workflows for schools, caregivers, and drivers. You architect the customer experience for high-stakes, multi-stakeholder interactions, ensuring safety, reliability, and clarity are baked into every workflow. You partner deeply with engineering, operations, and design to translate messy, real-world problems into scalable software solutions that delight both internal teams and external customers. You lead the discovery, prioritization, and execution of initiatives that drive operational efficiency, reduce friction, and improve outcomes across the entire support lifecycle. You are the voice of the customer and the voice of the business, balancing qualitative insights with quantitative metrics to guide product decisions. You build and maintain the product narrative that aligns cross-functional stakeholders and keeps complex initiatives moving forward. You thrive in ambiguity, using data and empathy to make timely decisions in a fast-moving, mission-critical environment.

Key facts

What you'll do

Define and own the product vision and roadmap for the Support and Operational Productivity suite, aligning on outcomes, metrics, and milestones with stakeholders across the organization.

Translate complex operational workflows and customer pain points into clear product requirements, user stories, and acceptance criteria that guide engineering and design.

Partner with support operations, safety, sales, and revenue teams to identify opportunities, prioritize initiatives, and measure impact on customer and operational KPIs.

Conduct ongoing discovery and synthesizing qualitative and quantitative data to inform product decisions, balancing user needs with business objectives.

Collaborate closely with designers to translate insights into intuitive, accessible, and consistent user experiences that support high-volume, high-risk workflows.

Work alongside engineers to break down epics into iterative deliverables, manage dependencies, and adapt plans as new information emerges.

Define and track product metrics and success indicators, using insights to iterate on features and drive continuous improvement across support processes.

Represent the product in cross-functional discussions, facilitating alignment and decision-making across teams with competing priorities.

Communicate progress, rationale, and tradeoffs clearly and persuasively to both technical and non-technical audiences, from executives to individual contributors.

Champion best practices in product development, including documentation, roadmaps, release planning, and stakeholder management.

Contribute to the broader product culture at HopSkipDrive by sharing learnings, frameworks, and playbooks that raise the bar for product excellence.

Engage directly with customers and internal users through research, interviews, and usability testing to build empathy and validate product assumptions.

Support the evaluation and implementation of AI-driven tools and workflows that enhance productivity, safety, and accuracy in operational processes.

Maintain a deep understanding of regulatory, compliance, and safety requirements relevant to student transportation and ensure product decisions reflect these needs.

Requirements

Minimum of 8 years of experience in product management, ideally spanning customer-facing platforms, operational tooling, or internal systems in complex, multi-stakeholder environments where reliability and user experience are non-negotiable.

Strong Customer Instincts: a proven ability to build genuine, nuanced understanding of users through research and data, and to translate those insights into product decisions that matter.

Strategic Vision & Execution: You think in systems and over horizons. Skilled at defining multi-year product strategies, cutting through ambiguity to set clear direction, and driving execution from ideation through growth. You can zoom out to shape a roadmap and zoom in to unblock a team - and you know when to do each.

Cross-Functional Collaboration: A proven partner to teams across the organization. You navigate competing priorities, broker alignment, and build the kind of collaborative relationships that make hard things possible. You understand that great product outcomes emerge from diverse perspectives working in concert.

Comfort with Data and Ambiguity: You make decisions in the absence of perfect information, using data, heuristics, and stakeholder input to guide choices and reduce risk.

Operational Mindset: You have a deep respect for operations and the people who keep the business running, and you build products that support their well-being, efficiency, and safety.

Communication Skills: You write clearly, speak persuasively, and tailor your message to your audience, whether you are explaining tradeoffs to executives or guiding a new engineer through a complex workflow.

Ownership and Bias for Action: You take initiative, follow through on commitments, and hold yourself and others accountable for results.

High Integrity and Judgment: You navigate complex tradeoffs with honesty, transparency, and a strong sense of ethical responsibility.

Nice to have

Experience working in education, transportation, or regulated industries, or with mission-critical, safety-sensitive services.

Background in AI product development or experience working alongside data scientists and ML engineers.

Experience with workforce management, routing, or logistics systems that involve dynamic scheduling and real-time coordination.

Practical notes

This is a full-time role based in Remote USA.

The compensation range for this role is $160,000 - $200,000 USD, plus equity and benefits.

This role reports to the Head of Support and Operational Productivity.

We use AI every day at HopSkipDrive, and not as a productivity add-on. It is woven into how we work at every level. If you have already built AI into how you work, you will hit the ground running. If you haven't, you will need to be ready to learn fast and work differently than you have before.