FleetWorks

| The freight industry is a two-sided marketplace that moves over a trillion dollars in goods every year, but the communication between the two sides—Carriers and Brokers—is often broken, manual, and inefficient. FleetWorks is fixing that. FleetWorks is building AI agents that automate the heavy lifting for both sides of the transaction, transforming a chaotic booking process into a modern, intelligent workflow. To succeed, we need a strategic storyteller who can speak two languages fluently: the operational, speed-focused language of brokers, and the relational, trust-based language of carriers. We are looking for a creative builder to join us in San Francisco and own our product positioning and packaging from the ground up. You will be the strategic hub between Product, Sales, and the market, defining how we sell our vision to two distinct audiences without ever contradicting our core brand promise. What you'll do Own Positioning & Packaging: Develop distinct value propositions, pricing strategies, and packaging for our Carrier and Broker products. You will define how we win on both sides of the marketplace. Master the Multi-Audience Narrative: Craft messaging that resonates with the specific pain points of a freight broker and a carrier while maintaining a cohesive "FleetWorks" brand voice that retains trust from both sides. Build Breakthrough Product Launches: Coordinate releases with product and sales to ensure every release lands with impact and clarity. Create enablement materials that drive adoption across both audiences. Bridge the Gap: Act as the translator between the product team’s technical innovations and the market’s needs. You will synthesize feedback from both audiences to influence the roadmap. Build the Growth Engine: Create the collateral, case studies, and sales enablement materials that help our growth teams close deals and our users realize value immediately. Execute Multi-Channel Campaigns: Own end-to-end execution—email, video, social, landing pages. Write copy, direct creative, run A/B tests, iterate fast. You’ll have the AI tools you need at your disposal to move quickly in bringing your breakthrough creative ideas to life. What we look for Comfortable with competitive markets: You have experience marketing products in crowded, noisy industries (e.g., fintech, adtech, cybersecurity). You know how to carve out space, differentiate, and win when features are commoditized and attention is scarce. Dual-Audience Expertise: You have experience marketing to different stakeholders within the same industry. You understand how to segment messaging so that it lands perfectly with one group without alienating the other. Breakthrough creative thinker: Marketing is changing rapidly and competition for attention is steeper than ever. You instinctively find ways to take marketing plans and creative the extra mile to break through the noise. A "Builder" Mindset: You have a startup mentality and thrive in ambiguity. You can develop high-level strategy for a product launch one hour and be deep in the weeds of editing landing page copy the next. Exceptional Storytelling: You can distill complex technical capabilities (like conversational AI) into simple, human benefits. You are a strong writer who values clarity over jargon. AI Native: You view AI not as a shortcut for quality, but as a lever for speed and scale. You know how to prompt, iterate, and refine AI outputs to meet a high bar. How we'll get to know each other Quick call with Bailey or Megan from the people team, to share your goals, what you’ve built that you’re proud of, and see if there is alignment. Portfolio / Case Study Review: We'll ask you to share examples of product launches you’ve led or positioning work you’ve developed for complex audiences. Live Strategy Session: A 45-min session with a founder to jam on a theoretical launch plan or messaging framework for a new feature. Paid Work Trial: A short, paid project where you might draft a positioning doc or outline a launch sequence, so we can see how you think and you can get to know us. Reference Check: We talk with your references to understand how to best support your development. Transparent Offer: Clearly outlining cash, equity, and value. What we offer Top tier cash and equity compensation: We aim to be above the 75th percentile for high-growth startups. Competitive benefits: Medical, dental, and vision. SF HQ Culture: A vibrant in-office culture in San Francisco where we build, learn, and solve hard problems together in person. High-velocity growth: The opportunity to learn quickly, shape a brand from scratch, and be rewarded for your impact.

| Every year, companies spend over a trillion dollars moving freight across the U.S - yet the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that. We’re building voice agents that turn the chaotic freight booking process into a modern, intelligent marketplace. Carriers, mostly small businesses and owner-operators, are the foundation of that system. Unlocking widespread carrier adoption is one of the highest-leverage opportunities in the company and a core driver of our long-term trajectory. We’re looking for a Product owner who has owned and scaled products that became the industry standard, someone who knows what excellence looks like because they’ve built it. You’ll define the vision, strategy, and execution for our Carrier Voice AI product line, shaping how AI interacts with millions of real-world shipments and building the interface that carriers rely on every day. This is not an incremental role: you’ll work directly with our founders to build a category-defining product from first principles and influence the direction of FleetWorks for years to come. What you’ll do: Own the vision, strategy, and roadmap for our Carrier Voice AI product line. Build and refine the core carrier experience, shaping how AI interacts with real-world freight workflows and becomes the default interface carriers rely on. Drive execution end to end, partnering closely with engineering, operations, and GTM to ship fast, iterate, and deliver measurable results. Set the bar for product excellence, establishing how we scope, prioritize, launch, and learn as we scale the product and the team. What we look for: A product leader with a history of building high-impact, category-defining products. A 0→1 builder who thrives in ambiguity, scales products from first principles, and makes fast, high-judgment calls. A systems thinker with strong customer instincts, comfortable with both ground-truth insights and data. An owner with a founder’s mindset, operating close to the work and holding an exceptionally high bar. (Freight experience is helpful but not required.) What we offer: Top-tier cash and equity compensation (above the 75th percentile for SF Series A companies) Competitive medical, dental, and vision benefits Fully covered lunches and dinners A chance to build fast, learn fast, and materially shape the future of FleetWorks

| Every year, companies spend over a trillion dollars moving freight across the U.S - yet the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that. We’re building voice agents that turn the chaotic freight booking process into a modern, intelligent marketplace. Carriers, mostly small businesses and owner-operators, are the foundation of that system. Unlocking widespread carrier adoption is one of the highest-leverage opportunities in the company and a core driver of our long-term trajectory. We’re looking for a Product owner who has owned and scaled products that became the industry standard, someone who knows what excellence looks like because they’ve built it. You’ll define the vision, strategy, and execution for our Carrier Voice AI product line, shaping how AI interacts with millions of real-world shipments and building the interface that carriers rely on every day. This is not an incremental role: you’ll work directly with our founders to build a category-defining product from first principles and influence the direction of FleetWorks for years to come. What you’ll do: Own the vision, strategy, and roadmap for our Carrier Voice AI product line. Build and refine the core carrier experience, shaping how AI interacts with real-world freight workflows and becomes the default interface carriers rely on. Drive execution end to end, partnering closely with engineering, operations, and GTM to ship fast, iterate, and deliver measurable results. Set the bar for product excellence, establishing how we scope, prioritize, launch, and learn as we scale the product and the team. What we look for: A product leader with a history of building high-impact, category-defining products. A 0→1 builder who thrives in ambiguity, scales products from first principles, and makes fast, high-judgment calls. A systems thinker with strong customer instincts, comfortable with both ground-truth insights and data. An owner with a founder’s mindset, operating close to the work and holding an exceptionally high bar. (Freight experience is helpful but not required.) What we offer: Top-tier cash and equity compensation (above the 75th percentile for SF Series A companies) Competitive medical, dental, and vision benefits Fully covered lunches and dinners A chance to build fast, learn fast, and materially shape the future of FleetWorks