[Hiring] Senior Product Manager @Work Truck Solutions

Role Description

We are seeking a Senior Product Manager to own a core area of the platform end to end—from the problem definition through to the metric that proves it worked. This is not a backlog-grooming role. Our users are dealers, upfitters, OEMs, and fleet buyers whose workflows are genuinely complicated, whose data is genuinely messy, and who will tell you plainly when software wastes their time. You will spend real hours in the field understanding how a fleet buyer thinks about their truck, how it gets specced, upfitted, listed, and sold, then translate that into products that make the whole supply chain faster. You will also help define how AI shows up in our products—which parts of these workflows should be automated, augmented, or left alone—and hold the line on quality when the easy answer is to ship a demo. You'll work closely with design, engineering, and data to sequence work that compounds, and you'll be measured on outcomes for the business and our customers rather than on shipping velocity.

Key Responsibilities

• Own strategy, roadmap, and execution for our Consumer shopping experience, including the tradeoffs required to keep it focused.
• Develop deep, first-hand understanding of dealer, upfitter, OEM, and fleet buyer workflows through customer conversations, ride-alongs, support data, and usage analytics.
• Write crisp problem definitions, specs, and success criteria that give engineering and design room to solve rather than instructions to follow.
• Define and instrument the metrics that matter for your area; run the analysis yourself rather than waiting on a request queue.
• Partner with design on discovery and validation, and with engineering on sequencing, scope, and technical tradeoffs.
• Identify where AI and ML meaningfully improve the product—data enrichment, search and matching, workflow automation, decision support—and scope those bets with honest evaluation criteria and clear failure modes.
• Drive launches end to end: enablement for sales and support, customer communication, adoption tracking, and iteration after release.
• Communicate up and out: keep executives, GTM teams, and customers aligned on what's coming, what changed, and why.
• Contribute to the broader product operating model—discovery practices, prioritization frameworks, and how the team makes decisions.

Qualifications

• 6+ years in product management, with at least one area or product line you owned end to end and can speak to in detail—including what didn't work.
• Demonstrated experience with complex B2B or marketplace products, ideally multi-sided, where different user groups have conflicting incentives.
• Strong discovery instincts: you talk to users regularly, you distinguish what they ask for from what they need, and you kill your own ideas when the evidence says to.
• Excellent written communication; your specs and updates reduce ambiguity rather than add to it.
• Track record of shipping meaningful outcomes in an Agile environment, and comfort operating without perfect information.

Requirements

• Self-sufficient with data: you write your own SQL or work fluently in your analytics stack, build your own dashboards, and don't outsource your understanding of your own metrics.
• Comfortable with experimentation and measurement—choosing the right metric, sizing impact honestly, and knowing when an A/B test isn't the right tool.
• Enough technical depth to hold a real conversation about APIs, data models, integrations, and system constraints, and to earn engineering's respect in design review.
• Experience with data-heavy products where the quality and structure of the underlying data is itself the customer problem.

AI and ML Product Capability

• Has shipped AI or ML features in production and can explain the tradeoffs made—not just the launch, but the evaluation approach, the failure cases, and what you did about them.
• Practical understanding of what current AI is and isn't good at, and the judgment to say no to AI features that create more customer risk than value.
• Comfortable defining quality bars for probabilistic systems: what accuracy is good enough, how errors surface to users, what the fallback is, and how you monitor degradation over time.
• Understands the economics—inference cost, latency, human-in-the-loop review—and can build a business case that survives contact with those numbers.
• Fluent with AI tooling in your own workflow (research synthesis, prototyping, analysis, drafting) and able to raise the team's practice without overselling it.
• Able to partner credibly with data science and ML engineering: you can scope a model problem, interpret an evaluation, and push back when a metric doesn't reflect the user's reality.

Working Style

• High ownership and low ego; you'll do the unglamorous work when it's what the customer needs.
• Demonstrated influence without authority across engineering, design, sales, and support.
• Bias toward shipping and learning over exhaustive planning, paired with the discipline to follow through past launch.
• Bachelor's degree or equivalent practical experience.
• Currently resides in one of the following states: CA, TX, FL.

Nice to Have

• Experience in automotive, dealership software, logistics, supply chain, fleet, or industrial B2B.
• Background with catalog, taxonomy, configuration, or inventory data products.
• Experience introducing AI capabilities into an existing product rather than building AI-native from scratch.
• Comfort with field research in non-office environments—dealerships, upfit shops, service bays.

Benefits

• Remote Flexibility: Work from anywhere in the U.S. while staying connected to a collaborative team.
• Impactful Work: Contribute to products that are reshaping the commercial vehicle industry.
• Growth Opportunities: Be part of a rapidly growing company with ample opportunities for professional development.
• Inclusive Culture: Join a team that values diversity, creativity, and innovation.

Ready to Drive Innovation?

If you want to own a product area where the problems are real, the users are direct, and the impact shows up in American businesses getting the vehicles they need to work, we'd love to hear from you. Apply now or reach out to us at [email protected] with your resume.