Product Manager - AI

About TruckSmarter

Logistics is one of the single largest industries in the world. Globally, logistics is an $8-$12 trillion dollar industry and in the US alone, ~$2 trillion, representing ~10% of GDP. A single percent of improvement drives profound change to every corner of the world—from the cost of our goods, to the livelihoods of local communities, to even the impact on our environment. To reshape the industry, at TruckSmarter, our focus is first on truck drivers. Trucks move 71% of freight in America (~$800bn annually) & the trucking industry represents nearly 6% of the full-time jobs in the country. If you look around you, every item has sat on a truck at one point on its journey to you. However, despite the industry being one of the greatest levers of innovation throughout history, it is still deeply fragmented & structurally misaligned. Our mission is to fix that—and we need your help.

The Role

We're hiring our first external Product Manager to help shape the future of how truck drivers and small fleet operators work, earn, and thrive. As a member of our growing product team, you'll take the lead on core product surfaces that directly impact growth, retention, and user engagement. This role is highly cross-functional, blending product thinking, executional drive, and empathy for our users–the backbone of the American supply chain.

We’re looking for someone who thrives in ambiguity, enjoys building light processes that scale, and brings a mindset of ownership and continuous learning. If you’re passionate about helping users succeed, excited by the potential of AI-enabled software, and eager to work alongside a sharp, mission-driven team we’d love to meet you!

What Excites You

• Creating great user experiences that improve growth, activation, and retention across the product journey. Empowering users through smart, intuitive, and trustworthy AI—especially those who are not traditionally tech-savvy.

• Contribute to broader company strategy. Partner with leadership to see around corners and work back from broad strategic plans down to narrow execution details. Own the process, own the outcome.

• Working closely with engineers and designers to build, ship, and iterate quickly. Whether Launching a new onboarding flow or refining an AI-driven tool.

• Running experiments along side operations to validate hypotheses, learning through data and feedback, and using both to guide roadmaps.

• Operating in a fast-moving, resourceful team that values impact over process. Wearing many hats and digging into everything from metrics to support tickets to customer calls.

What Excites Us

• 3–5 years of product management experience, ideally in consumer, prosumer, or SMB B2B SaaS.

• Strong product intuition paired with a track record of shipping meaningful, measurable improvements to user growth and retention.

• Experience working on AI- or ML-powered products, or a strong desire to build in that space.

• Comfortable leading with clarity even when full specs don’t exist—you’re the kind of person who builds the right level of structure as you go.

• You make others better: you unblock teams, elevate the quality of execution, and build trust with cross-functional partners.

• Hands-on operator: You’re comfortable rolling up your sleeves, getting in the weeds, and driving progress directly.

• A demonstrated curiosity about how things work, how users behave, and how to build better systems over time.

What Success Looks Like

• You've successfully owned a large portion of the product surface from roadmap through launch, balancing user needs, business goals, and technical constraints.

• Growth and retention metrics for your product area are clearly defined, improving, and well understood across the team.

• AI features have been delivered in your product area that meaningfully reduce friction, save time, or increase user confidence.

• The teams you work with trust your judgment, operate more efficiently, and value your leadership.

We Offer

• Health, Dental & Vision Plans

• Competitive Pay

• 401k

• Unlimited PTO

• Lunch + dinner daily

• Commuter benefits

Working model: TruckSmarter offers an in-office collaborative culture. This role is based out of our downtown San Francisco office 5 days/week.

We would love to have you be a part of something special, and are excited to review your application!