Senior Customer Success Manager

FleetWorks; Chicago (IL); On-site; USD 70,000 - 90,000; Full time

Job summary

A leading freight technology company is hiring for a Customer Success role in Chicago. As the second member of the customer success team, you'll manage customer lifecycles, ensure successful implementation, and collaborate with engineering for technical integrations. Ideal candidates have B2B customer success experience, especially in freight tech, and possess a builder mindset for building processes and playbooks. Join a transformative mission in the complex freight industry.

Qualifications

• Professional experience in B2B customer success, account management, or sales engineering.
• Experience managing large, multithreaded accounts in the freight tech industry.
• Ability to work hands-on with complex requirements and configurations.

Responsibilities

• Manage the full customer lifecycle for critical relationships.
• Program manage high-stakes pilots and implementations.
• Work closely with Engineering to deliver on customer integration requirements.
• Build the customer success foundation by creating documentation and establishing procedures.
• Drive ongoing customer education on platform features.

Skills

B2B customer success experience

Enterprise level freight tech experience

Technical aptitude

Builder mindset

Problem-solving attitude

Job description

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.

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 management, sales engineering or implementation, in an entrepreneurial environment.

• Must have Enterprise level freight tech experience, you will be managing large, multithreaded broker accounts and smaller firms.

• A "builder" mindset: You are excited to be the second member of the team and want to work on 0-1 projects like building playbooks and defining processes.

• Technical aptitude: You are comfortable working hands on with complex requirements gathering and configurations and collaborating with engineers to make sure we deliver on our promise.

• A healthy appreciation for hard problems—we are transforming a massive, complex industry and we’re just getting started.

How we'll get to know each other

• 45 minute intro call, what you’ve worked on that you’re proud of, your goals and motivations and to figure out how that might fit in with what we’re working on at FleetWorks.

• 45‑min interview with a team member you'll work with if you join, so that we can get to know how you think about customer success and collaboration.

• Case study or presentation to see how you approach customer challenges.

• Paid onsite work trial so that we can get to know how you work and you can get to know us.

• We'll talk with your references to help us understand how to best