Deployment Strategist

FleetWorks is building the next generation of conversational AI to automate complex workflows for freight carriers and brokers. Our sales cycle is highly consultative, focusing on proving measurable value through custom-built solutions before a deal is signed.

We are looking for a Deployment Strategist to be the technical and creative backbone for prospects and customers.
This role is a direct link between our customers operational challenges and tangible solutions built on the FleetWorks platform. You will be embedded within the GTM organization to design, build, and demonstrate custom AI agents that prove our value and convert pipeline into closed deals and long term partnerships.

This is a high-impact, hands-on role that requires a blend of business acumen, technical curiosity, and an execution-focused mindset. This role is based full time out of our office in Chicago.

• 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.

• Technical Aptitude: Strong comfort with new software and systems. You are a fast learner who can quickly grasp the mechanics of AI configuration, prompting, and technical deployment.

• Problem-Solving & Detail Orientation: A high degree of organization and meticulous attention to detail is required to manage and maintain complex demo environments and deployment checklists.

• Foundational Experience: 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)

• Communication Skills: Clear and professional written and verbal communication, with the ability to articulate technical configurations in an understandable way to both internal sales and external prospects.

• Startup Mentality: Eagerness to jump in, assist where needed, and own execution tasks in an ambiguous, rapidly evolving environment.

• Process Driven: A natural inclination toward creating process and order in a chaotic environment.

• Top tier cash and equity compensation: We aim to be above the 75th percentile for high-growth startups.

• Competitive benefits: Medical, dental, and vision.

• Vibrant Office Cultures: A vibrant in-office culture in our San Francisco and Chicago offices 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.