VP of Product

About the role

The company is seeking a VP of Product to lead and scale the product organization as it enters its next stage of growth. This leader will set a bold, customer-backed vision for an AI-native logistics platform, bring ROI rigor to how we size and prioritize bets, grow the PM team, and be the face of the company's roadmap in front of customers.

What you will do

• Set and own the company's product vision and roadmap.

• Bake AI into the core of the product so it feels native, not bolted on. No chat sidebars or sparkle buttons. AI should quietly take over the dispatch, routing, pricing, and support decisions people make by hand today, inside the workflows they already use.

• Build ROI discipline into the roadmap by putting a value on every opportunity and prioritizing against it, the way Sales manages pipeline value. For automation, that means valuing bets by the ops work they remove.

• Close the loop on every bet: define success metrics before building, instrument what ships, and compare actual results against the original estimate. Use that track record to sharpen future sizing.

• Work with the executive team to turn company strategy into a focused, prioritized product plan, and represent that plan to leadership.

• Partner with Engineering as a true thought partner to work through trade-offs, drive execution, and ship on fast cycles.

• Stay close to customers so you understand their workflows and the decisions the platform needs to power. Evangelize the roadmap through customer advisory boards, key account conversations, and joint pitches with Sales that build excitement and help close deals.

• Get on sales calls for strategic deals. Run product demos, handle product objections and gaps directly, and help shape what we commit to in enterprise contracts. Bring win/loss patterns back into the roadmap.

• Own quality for AI-driven features, including evals, failure modes, cost, and latency, and the guardrails customers need before they trust automation in their operations.

• Set the bar for how the PM team works with AI: prototyping with AI tools instead of writing long specs, and moving from idea to working demo in days.

• Lead and grow the product management team from three PMs today toward four to six, spending most of your time on leadership and cross-functional work with Engineering, Growth, Operations, and the exec team.

What you need to have

• 10+ years in product, including 4+ years managing product managers, with a track record of growing into product leadership where the title reflected real scope.

• Strong conviction as a product visionary: you form a clear point of view on where the product should go, ground it in customer evidence, and hold it steady against competing priorities.

• Real energy for customer-facing work, from running customer advisory boards to pitching the roadmap alongside Sales, with the ability to leave customers excited about what is coming.

• Experience supporting enterprise sales cycles, including demos, product objections, RFPs, and security or integration reviews, with a track record of helping close deals without overcommitting the roadmap.

• Business and ROI rigor: experience building business cases for product investments and using opportunity sizing to make and defend prioritization calls.

• Strong product analytics instincts. You can define the metrics that matter, pull your own data from tools like PostHog or SQL, and run experiments and staged rollouts without waiting on a BI team.

• Shipped AI or ML features to production that users experienced as part of the product rather than a separate add-on, and stayed with them after launch through the messy parts: evals, edge cases, and adoption.

• Personal fluency with current AI tools. You use them every day, build prototypes yourself, and have opinions on what is hype and what is leverage.

• A hands-on leadership style that pairs executive communication and cross-functional influence with a willingness to roll up your sleeves and do the work alongside the team, rather than managing from a distance.

Bonus points for

• Product leadership experience at a marketplace company.

• Having built agentic or automation products in operations-heavy domains like logistics, marketplaces, or field services.

• Having built or scaled a product org at a similar growth stage.

• Having brought a new layer of discipline, such as ROI modeling or opportunity sizing, to a product team that lacked it.

What is in it for you?

• Real space to shape, or overhaul, the roadmap of an AI-native platform, with big bets ahead in automation, internationalization, and expansion into new verticals.

• The chance to build and scale the PM team as a true peer to Engineering and Growth leadership.

• Competitive salary, equity compensation, and comprehensive benefits (health, dental, vision, 401K).

• Remote-friendly with preference for Ventura, CA office presence.

• A high-growth, mission-driven environment where your work has direct and measurable impact.

Who are we?

We are the company, and our mission is to build the network and software that move the world’s goods with speed, intelligence, and trust. The company provides on-demand, last-mile logistics for construction and adjacent industries with our nationwide fleet of cars, trucks, and flatbeds.

Founded in 2018 and part of the YC S19 Batch, we’re solving the massive inefficiencies that exist in the construction industry. Our headquarters are in Ventura, CA. Learn more at the company [link for members]

The company is an equal opportunity employer and complies with all applicable federal, state, and local fair employment practices laws. All qualified applicants will receive consideration for employment. We don't discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.