Deployment Analyst

FleetWorks is seeking a Deployment Strategist to serve as the technical and creative link between customer operational challenges and AI solutions. This role involves designing, building, and demonstrating custom AI agents to prove value, convert pipeline, and foster long-term partnerships. It's a high-impact, hands-on position requiring business acumen, technical curiosity, and an execution-focused mindset, based full-time in Chicago.

Must Have

• Support use case definition by gathering customer requirements and translating business needs into AI agent solutions.
• Develop sales assets like slides, ROI calculators, and use case one-pagers.
• Execute Proof of Concepts (POCs) by building and configuring custom AI agents and demo environments.
• Document successful deployment playbooks and maintain a library of use case examples.
• Facilitate feedback loop from customers and sales to Product and Engineering teams.
• Strong comfort with new software and systems, fast learner of AI configuration, prompting, and technical deployment.
• High degree of organization and meticulous attention to detail.
• 1-3 years of experience in an entrepreneurial product or customer-facing role.
• Clear and professional written and verbal communication.
• Eagerness to jump in, assist, and own execution tasks in a rapidly evolving environment.
• Natural inclination toward creating process and order.

Perks & Benefits

• Top tier cash and equity compensation (above 75th percentile for high-growth startups).
• Competitive benefits (Medical, dental, and vision).
• Vibrant in-office culture in San Francisco and Chicago offices.
• Opportunity for high-velocity growth, learning quickly, and shaping a brand.

Location

Chicago

Employment Type

Full time

Location Type

On-site

Department

Operations

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.

What you'll do

• 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.

What we look for

• 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.

What we offer

• 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.