Implementation Strategist
FleetWorksChicago, Illinois, United States • San Francisco, California, United States
Posted January 9, 2026
Full Time
About the Company
FleetWorks builds a voice-first AI assistant that streamlines logistics operations for freight brokers and carriers, automating repetitive tasks that traditionally slow down the supply chain. By integrating natural-language interfaces with real-time data, the platform reduces manual paperwork, speeds up booking and tracking, and improves visibility across the network. The solution is backed by prominent investors such as First Round Capital, Saga Ventures, and Y Combinator, underscoring its potential to reshape the freight brokerage industry. FleetWorks' focus on conversational AI and end-to-end automation positions it as a distinctive player that empowers logistics professionals to reclaim time and reduce operational friction.
Job Description
FleetWorks is building the next generation of conversational AI to automate complex workflows for freight carriers and brokers. We are looking for a Deployment Strategist to be the technical and creative backbone for prospects and customers, designing, building, and demonstrating custom AI agents that prove our value and convert pipeline into closed deals and long term partnerships.
Requirements
- Strong technical aptitude with new software and systems
- 1-3 years of experience in an entrepreneurial product or customer-facing role
- Problem-solving and detail orientation
- Foundational experience in analytics, product, customer success, sales enablement, technical support, or similar roles at a VC-backed startup
Benefits
- Top-tier cash and equity compensation
- Competitive benefits (medical, dental, and vision)
- Vibrant office culture in San Francisco and Chicago offices