Chief of Staff

FleetWorks is rebuilding the $1 trillion freight marketplace with AI. Every year, companies spend over a trillion dollars moving freight across the U.S. — but the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that.

We’re turning today’s chaotic freight market into a modern, intelligent marketplace — one where AI agents replace the endless phone calls, texts and emails and match jobs to trucks instantly.

This is a high-trust, high-impact role ideal for someone who thrives in ambiguity, enjoys building systems from scratch, and wants a front-row seat to company-building. The ideal candidate sees this role as a stepping stone to starting their own company.

Key Responsibilities

• Strategic Projects: Own high-priority, cross-functional projects from idea to execution. Examples may include go-to-market experiments, customer research, pricing strategy, or internal automation.
• CEO Enablement: Act as a thought partner to the CEO — preparing materials, managing priorities, and ensuring follow-through on key decisions.
• Board & Investor Support: Coordinate board meetings, investor updates, and data room prep.
• Culture Stewardship: Help shape and protect the company culture as we scale.
  
  

Who You Are

• 3 years of experience in high-growth startups, consulting, investing, or operations.
• Has worked in or around logistics or is very excited to learn about the industry.
• Comfortable communicating with enterprise executives or SMB business owners.
• Exceptionally organized and detail-oriented, but not bogged down by perfectionism.
  
  

Why This Role

• Work directly with the CEO and founding team
• Gain exposure to every function of a fast-growing startup
• Help scale a leading AI agent company solving real problems
• Fast path to leadership opportunities as the company grows
  
  

What We Offer

• Health plan
• Unlimited PTO
• Fully covered lunches and dinners.