FleetWorks · 1 day ago
Deployment Strategist
Chicago, IL
Full-time
Onsite
Entry Level
1+ years expFleetWorks is building the next generation of conversational AI to automate complex workflows for freight carriers and brokers. They are seeking a Deployment Strategist to serve as the technical and creative backbone for prospects and customers, focusing on designing and demonstrating custom AI agents to convert pipeline into closed deals.
Transportation/Trucking/Railroad
Responsibilities
Support Use Case Definition: Work closely with the commercial team from pre-sales to upsell to gather customer requirements and help translate business needs into defined, actionable AI agent solutions
Develop Sales Assets: Create and maintain internal sales enablement materials (e.g., slides, ROI calculators, use case one-pagers) that the sales team can use to articulate the value of various AI solutions in the early stage of the sales funnel
Execute Proof of Concepts (POCs): Take the lead on the technical build and configuration of custom AI agents and demo environments to validate the FleetWorks platform’s value for a specific customer use case
Document and Organize: Assist in documenting successful deployment playbooks and maintaining a centralized library of successful use case examples and configuration best practices
Facilitate the Feedback Loop: Systematically gather, document, and relay customer and sales team feedback from pilot programs to the Product and Engineering teams to help inform future product iteration
Qualification
Required
Strong comfort with new software and systems
Fast learner who can quickly grasp the mechanics of AI configuration, prompting, and technical deployment
A high degree of organization and meticulous attention to detail
1-3 years of experience in an entrepreneurial product or customer-facing role (e.g., Analytics, Product, Customer Success, Sales Enablement, Technical Support or a similar role at a VC backed startup)
Clear and professional written and verbal communication
Ability to articulate technical configurations in an understandable way to both internal sales and external prospects
Eagerness to jump in, assist where needed, and own execution tasks in an ambiguous, rapidly evolving environment
Natural inclination toward creating process and order in a chaotic environment
Benefits
Medical, dental, and vision.
Vibrant in-office culture in our San Francisco and Chicago offices where we build, learn, and solve hard problems together in person.
Company
FleetWorks
Backed by Y Combinator Automating the 1B+ phone calls the freight industry makes every year
11-50 employees
H1B Sponsorship
FleetWorks has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (1)
Funding
Current Stage
Early StageCompany data provided by crunchbase