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FleetWorks is fixing that. We're building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved. We're expanding our forward-deployed engineering team in Chicago, a major hub for our customers and the heart of U.S. freight operations. In this role, you'll be embedded directly into the environments where our product meets real users. You'll work side-by-side with operators, understand their workflows firsthand, and turn that knowledge into robust integrations and production features. As our first Forward-deployed engineer at FleetWorks, you'll own outcomes end-to-end: diagnosing messy real-world problems, shaping technical solutions in the field, and ensuring our AI agents perform flawlessly in live operations. If you thrive in ambiguous environments, enjoy working directly with customers, and want to see your code deliver immediate operational impact, this role is uniquely high-leverage. 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Get In Touch at FleetWorks - San Francisco | OnSite | Chicago - Get In Touch San Francisco | OnSite | Chicago Interested in joining FleetWorks but nothing we have open right now is quite right? Share your information here and join our Talent Network. We'll review these submissions as we open new roles and reach out if there is a fit.

", "datePosted": "2026-06-10T03:52:15.000Z", "employmentType": "OTHER", "identifier": { "@type": "PropertyValue", "name": "FleetWorks", "value": "b834103aae444754d39fe2878410e85d" }, "hiringOrganization": { "@type": "Organization", "name": "FleetWorks" }, "jobLocation": { "@type": "Place", "address": { "@type": "PostalAddress", "addressCountry": "US" } }, "directApply": false, "experienceRequirements": { "@type": "OccupationalExperienceRequirements", "monthsOfExperience": 36 }, "educationRequirements": "no requirements", "url": "https://fewerjobs.com/jobs/fleetworks/get-in-touch-b834103a" } }, { "@type": "ListItem", "position": 2, "url": "https://fewerjobs.com/jobs/fleetworks/senior-product-engineer-ai-9858c7c4", "item": { "@context": "https://schema.org", "@type": "JobPosting", "title": "Senior Product Engineer - AI", "description": "

Senior Product Engineer - AI at FleetWorks - San Francisco - Senior Product Engineer - AI San Francisco 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 building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved. We have a small, high-agency team working out of our office in SOMA. As an early engineer, you will be a true owner of your work, developing features end to end, interacting directly with our customers, and shaping our culture. Learn about our series A here https://www.fleetworks.ai/blog/fleetworks-launches-always-on-dispatcher-for-trucking-industry-with-17m-funding! What you'll do - Own end-to-end feature development, working directly with a high-ownership team including our founders, customers, and other engineers - Make product and technical decisions that will shape the future of FleetWorks - Ship new work every day - Learn from others and teach those around you What we look for - Professional experience owning end-to-end feature development on customer-facing products - At least 4 years of professional full-time software development, including at least one 2 years or more at one company (or a company and its acquirer) - Comfort working in our stack or picking it up quickly-we use TypeScript across the stack - A healthy appreciation for hard problems-we already handle tens of thousands of phone calls and emails

", "datePosted": "2026-06-10T03:52:15.000Z", "employmentType": "FULL_TIME", "identifier": { "@type": "PropertyValue", "name": "FleetWorks", "value": "9858c7c4410ca032d0ebef4ecf0846f5" }, "hiringOrganization": { "@type": "Organization", "name": "FleetWorks" }, "jobLocation": { "@type": "Place", "address": { "@type": "PostalAddress", "addressCountry": "US" } }, "directApply": false, "experienceRequirements": { "@type": "OccupationalExperienceRequirements", "monthsOfExperience": 48 }, "educationRequirements": "no requirements", "url": "https://fewerjobs.com/jobs/fleetworks/senior-product-engineer-ai-9858c7c4" } }, { "@type": "ListItem", "position": 3, "url": "https://fewerjobs.com/jobs/fleetworks/senior-software-engineer-customer-platform-8b3816ae", "item": { "@context": "https://schema.org", "@type": "JobPosting", "title": "Senior Software Engineer - Customer Platform", "description": "

Senior Software Engineer - Customer Platform at FleetWorks - Chicago | OnSite | San Francisco - Senior Software Engineer - Customer Platform Chicago | OnSite | San Francisco 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 building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved. We're expanding our engineering team in Chicago, a major hub for our customers and the heart of U.S. freight operations. In this role, you'll be a full member of our core engineering team, but deployed directly into the environments where our product meets the real world. You'll build production features, design integrations inside messy customer systems, and shape the internal tooling and platform components that allow us to scale deployments efficiently. If you're a strong software engineer who wants to work hands-on with users, solve ambiguous problems on the ground, and see your code driving live operations within days, this is a uniquely high-leverage role. Learn about our Series A here! https://www.fleetworks.ai/blog/fleetworks-launches-always-on-dispatcher-for-trucking-industry-with-17m-funding WHAT YOU'LL DO: - Lead technical delivery for customer implementations, integrations, and workflow builds; owning projects from scoping through production rollout. - Architect and build workflows that encode real customer processes, integrating directly with their systems and adapting to operational edge cases you uncover in the field. - Develop core platform components and integration

", "datePosted": "2026-06-10T03:52:15.000Z", "employmentType": "OTHER", "identifier": { "@type": "PropertyValue", "name": "FleetWorks", "value": "8b3816aebb722d28a36767ffa58bd47e" }, "hiringOrganization": { "@type": "Organization", "name": "FleetWorks" }, "jobLocation": { "@type": "Place", "address": { "@type": "PostalAddress", "addressCountry": "US" } }, "directApply": false, "experienceRequirements": { "@type": "OccupationalExperienceRequirements", "monthsOfExperience": 60 }, "educationRequirements": "no requirements", "url": "https://fewerjobs.com/jobs/fleetworks/senior-software-engineer-customer-platform-8b3816ae" } }, { "@type": "ListItem", "position": 4, "url": "https://fewerjobs.com/jobs/fleetworks/senior-software-engineer-70101e6e", "item": { "@context": "https://schema.org", "@type": "JobPosting", "title": "Senior Software Engineer", "description": "

Senior Software Engineer at FleetWorks - Chicago | OnSite | San Francisco - Senior Software Engineer Chicago | OnSite | San Francisco 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 building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved. We have a small, high-agency team working out of our offices in SF and Chicago. As an early engineer, you will be a true owner of your work, developing features end to end, interacting directly with our customers, and shaping our culture. Learn about our series A here https://www.fleetworks.ai/blog/fleetworks-launches-always-on-dispatcher-for-trucking-industry-with-17m-funding! What you'll do - Own end-to-end feature development, working directly with a high-ownership team including our founders, customers, and other engineers - Make product and technical decisions that will shape the future of FleetWorks - Ship new work every day - Learn from others and teach those around you What we look for - Professional experience owning end-to-end feature development on customer-facing products - At least 4 years of professional full-time software development, including at least one 2 years or more at one company (or a company and its acquirer) - Comfort working in our stack or picking it up quickly-we use TypeScript across the stack - A healthy appreciation for hard problems-we already handle tens of thousands of

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Senior Customer Success Manager at FleetWorks - San Francisco | OnSite - Senior Customer Success Manager San Francisco | OnSite 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 building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved. We have a small, high-agency team working out of our office in SOMA. As the second member of the customer success team, you will be a true owner of your work, managing our most critical relationships and defining the customer success motion from the ground up. What you'll do - Manage the full customer lifecycle, acting as the primary owner from pilot kickoff through implementation, adoption, and renewal. - Program manage high-stakes pilots and implementations, ensuring timelines are met and customers realize immediate value from our platform. - Work closely with Engineering to scope and deliver on individual customer integration requirements, acting as the technical voice of the customer. - Build the CS foundation (0-to-1) by creating documentation, establishing operating procedures, and designing the engagement cadences we need to scale. - Drive ongoing customer education, ensuring users understand the full power of our voice agents and platform features. - Learn from others and teach those around you. What we look for - Professional experience in b2b customer success, account

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Senior Software Engineer - Forward Deployed at FleetWorks - Chicago | OnSite | San Francisco - Senior Software Engineer - Forward Deployed Chicago | OnSite | San Francisco 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 building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved. We're expanding our forward-deployed engineering team in Chicago, a major hub for our customers and the heart of U.S. freight operations. In this role, you'll be embedded directly into the environments where our product meets real users. You'll work side-by-side with operators, understand their workflows firsthand, and turn that knowledge into robust integrations and production features. As our first Forward-deployed engineer at FleetWorks, you'll own outcomes end-to-end: diagnosing messy real-world problems, shaping technical solutions in the field, and ensuring our AI agents perform flawlessly in live operations. If you thrive in ambiguous environments, enjoy working directly with customers, and want to see your code deliver immediate operational impact, this role is uniquely high-leverage. Learn about our Series A here! https://www.fleetworks.ai/blog/fleetworks-launches-always-on-dispatcher-for-trucking-industry-with-17m-funding WHAT YOU'LL DO: - Own customer deployments end-to-end, from initial scoping to integration design to production rollout. - Work directly with customer operators and leaders to understand real workflows, pain points, and edge cases, translating them into clear, high-quality technical solutions. - Build production features and

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