Manager of Mid-Market Customer Success

We Speak Safety and Efficiency:  

In September of 2024, Bestpass, Fleetworthy, ExpressTruckTax and Drivewyze rebranded as Fleetworthy. This rebrand reflects our ongoing mission to simplify fleet safety, compliance, and toll management under one unified brand.

Fleetworthy is revolutionizing road safety and fleet management with a command center for safety, compliance, and efficiency. Our connected suite provides real-time insights and control, enabling customers to maximize efficiency, reduce risk, and save money.

With technology that unifies safety, compliance, toll management, weigh station bypass, and more, Fleetworthy empowers organizations to perform at their best. We simplify operations to ensure every vehicle and driver is not just compliant, but beyond compliant.  Supporting millions of drivers and vehicles, Fleetworthy is leading a new era in road safety and fleet technology.   

At Fleetworthy, you’re in the driver’s seat! 

The Manager of Mid-Market Customer Success is a people leader within the Customer Experience organization, responsible for managing and developing a team of Mid-Market Customer Success Managers.  This role ensures the Fleetworthy Mid-Market Customer Success team delivers a high-quality customer experience at scale, drives measurable customer value, and strengthens long-term relationships with our mid-market accounts.  This leader will guide the team in handling complex customer needs, resolving escalations, analyzing account performance and improving customer engagement. The Manager will be accountable for team performance and coaching, operational excellence, and cross-functional alignment that supports customer growth, retention, and satisfaction.

 What Your Ride Will Look Like: 

• Lead, coach, and develop a team of Mid-Market CSMs to deliver exceptional service and value to our customers.
• Conduct regular 1:1s with CSMs focused on strategic account planning, performance evaluation, skill development and professional growth.
• Work with Customer Success leadership to ensure CSMs are equipped with playbooks, best practices, and processes that support customer health and retention.
• Guide your team in developing trusted-advisor relationships with key customer accounts.
• Resolve and manage the resolution of challenging escalated client requests and/or complex account demands. 
• Partner with customer success leadership to improve tools, workflows, and reporting that enhance team effectiveness.
• Ensure CSMs effectively evaluate client datasets and coach team on turning data into insights and actionable recommendations.
• Join key customer business reviews focused on recommendations for program optimization and opportunities to expand the business  
• Collaborate with Sales, Marketing, Product, and Support to ensure a unified customer experience and successful delivery of customer outcomes.
• Ensure Mid-Market team attainment of both performance and activity-based goals on a quarterly basis and proactively engage resources available to guide team in achievement of them.  

Requirements: 

• Bachelor's degree in Business, Communications or a related field
• 4-6 years of experience in Customer Success, Account Management or in a similar client-facing role, with at least 1-2 years in a leadership or team lead capacity
• Experience managing a book of mid-market or enterprise accounts preferred
• Strong leader who can coach, develop and motivate a team
• Excellent written and verbal communication and presentation skills
• Proficient in Microsoft Excel, PowerPoint and Word
• Excellent problem solving and executive-level relationship building skills
• Demonstrated ability to work cross-functionally with Sales, Product, Support, and Marketing.
• Familiarity with CRM systems like Salesforce, Planhat or Gainsight strongly preferred
• Comfortable operating autonomously in a fast-paced environment while also managing team structure and process
• Previous experience in the transportation industry is a plus, but not required 

What Drives Us to Work Every Day: 

• We pride ourselves on making a difference, for our employees, clients, and their businesses.
• We accept team members for who they are and what they bring