Job Title: Customer Success Manager
Location: San Francisco or Chicago
Reports to: CEO
Company: FleetWorks Technology, Inc.
Website: fleetworks.ai
FleetWorks is a Y Combinator and First Round-backed AI startup transforming the freight industry. Our flagship platform uses AI agents to help freight brokers book freight faster, more profitably, and with fewer human hours. We’re backed by top-tier investors and trusted by industry-leading brokerages like Sage Freight. This is a rare opportunity to join a fast-growing startup at the intersection of artificial intelligence and logistics.
We’re looking for a highly motivated Customer Success Manager to work directly with the CEO to build strong, lasting relationships with customers. This is a high-trust, high-impact role ideal for someone who thrives in ambiguity, is energized by direct communication with logistics operators, and wants a front-row seat to company-building. You’ll be a key bridge between our AI platform and the logistics companies that make the supply chain move.
Customer Success & Retention:
Serve as the primary point of contact for customers partners using the FleetWorks platform
Onboard new customers and ensure they are set up for success
Resolve issues proactively to maintain customer satisfaction and trust
Build customer-facing playbooks and best practices as we scale
Operational Efficiency:
Track and optimize customer performance metrics
Partner with Product and Engineering to identify platform improvements based on customer feedback
Help design and iterate internal workflows to increase automation and reduce friction
Relationship Building:
Nurture long-term partnerships with high-performing customers
Represent the voice of the customer inside FleetWorks and advocate for their needs
Attend industry events or host roundtables to deepen relationships and gather insights
Culture Stewardship:
Help shape and protect the company culture as we scale, especially in how we work with customers and partners
2+ years experience in a freight brokerage or 3PL
Comfortable working directly with both logistics leaders and boots-on-the-ground dispatchers
High ownership mindset; you take initiative and follow through
Bonus: Proficiency in Russian or Spanish
Work directly with the CEO and executive team
Gain exposure to every function of a fast-growing AI startup
Shape the future of how logistics companies interact with intelligent freight platforms
Fast path to leadership opportunities as the company grows
Benefits include:
Health plan
Unlimited PTO
Fully covered lunches and dinners
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As an Operations Manager at FleetWorks Technology, Inc., you'll be stepping into a dynamic role in the heart of Chicago, where technology meets logistics. FleetWorks is revolutionizing the freight industry using AI to make processes smoother and more profitable. In your role, you will be responsible for driving customer success and operational efficiency, working directly with the CEO as you nurture relationships with our customers. This means you get to onboard new clients, resolve issues proactively, and ensure that they get the most out of our innovative platform. Your insights will play a crucial role in enhancing customer performance metrics and advocating for their needs while collaborating closely with our Product and Engineering teams. Plus, you will help design internal workflows that pave the way for a more automated and frictionless experience not just for our customers, but for our entire team. If you are someone who thrives in fast-paced settings, has a strong ownership mindset, and has experience in freight brokerage or third-party logistics, you'll find this opportunity to be not just a job, but a chance to shape the future of logistics. Join us in creating powerful customer relationships and driving significant value at FleetWorks Technology, Inc. – a place where your contributions are highly valued, and the path ahead is filled with growth possibilities.
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