Head of Autonomous Carrier Operations

Our client is a well-funded, venture-backed freight technology company building AI-powered software that is transforming how freight brokerages operate. Following a recent round of funding and rapid customer growth, the company is entering its next phase of expansion while investing heavily in autonomous brokerage technology. Rather than simply automating repetitive tasks, the company is building AI that can think and make decisions the way the industry's best carrier sales professionals do. Their platform automates carrier communications, rate negotiations, compliance verification, and load booking while continuously learning how experienced brokerage professionals evaluate freight opportunities and solve complex transportation challenges. This is an opportunity to join a small, highly collaborative team where your expertise will directly influence the future of AI within freight brokerage. Position Overview This is not a traditional brokerage leadership role. You will not be responsible for managing freight, owning customer relationships, leading a carrier sales team, or carrying a revenue quota. Instead, you'll serve as the brokerage subject matter expert working alongside Product and Engineering teams to help build the intelligence behind an autonomous carrier sales platform. Your primary responsibility will be translating years of brokerage knowledge into scalable decision frameworks that teach AI how elite carrier sales professionals think. You'll help shape everything from carrier selection logic and negotiation strategies to lane prioritization, backhaul optimization, and decision-making workflows. The platform is already handling thousands of carrier interactions each day, and your expertise will directly influence how future generations of autonomous brokerage technology operate. What You'll Be Doing Partner closely with Product and Engineering teams to teach AI how experienced carrier sales professionals evaluate freight opportunities. Develop decision frameworks around carrier selection, negotiation strategy, lane prioritization, pricing, and capacity sourcing. Help define how the platform identifies the best carrier for each shipment. Analyze why certain loads succeed while others fail and improve the platform's decision-making logic. Build repeatable operational playbooks that transform brokerage intuition into scalable product intelligence. Refine carrier engagement strategies, follow‑up cadence, routing logic, and backhaul identification. Serve as the company's carrier sales subject matter expert during product development. Continuously improve autonomous performance across increasingly complex spot‑market freight scenarios. Work directly with company leadership to help shape the long-term product roadmap. What We're Looking For 8+ years of brokerage carrier sales experience. Deep expertise within spot market truckload brokerage. Strong understanding of carrier sourcing, negotiation strategy, pricing, capacity management, lane strategy, and carrier network development. Experience building or improving carrier sales processes, playbooks, or best practices. Ability to clearly explain the reasoning behind operational decisions rather than simply relying on instinct. Comfortable collaborating with technical teams, product managers, and software engineers. Genuine curiosity around AI, technology, and building innovative products. Entrepreneurial mindset with excitement for joining a fast-growing startup. What This Role Is Not This position is not focused on: Managing a carrier sales team Running brokerage operations Owning customer accounts Instead, this role focuses on helping build software that thinks like the industry's best brokerage professionals. Location & Schedule Based onsite in San Francisco, CA Six-day onsite workweek, including Saturdays Typical schedule is approximately 9:00 AM-7:00 PM, with more flexibility on Saturdays #J-18808-Ljbffr CS Recruiting