Manager of Mid-Market Customer Success
Drivewyze
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 to the table.
- We are proud to build all our relationships based on transparency and trust.
- We are a team of energetic and curious individuals passionate about the work we do every day!
Our Core Values – We are 1TEAM
- People 1st - People 1st! We win as a team by collaborating, having each other’s backs, and bringing out the best in each other. We always treat others as they would like to be treated.
- Trust - We inspire trust by delivering on our promises, owning outcomes, being transparent in our communications, and acting with integrity.
- Every Trip Matters - Because every trip that our customers take is important to them, it's important to us. Whether it is a load being hauled across the country or a service vehicle traveling on a toll road, our customers count on us to deliver the right expertise, software, and data to make every trip safe, efficient, and productive.
- Always Innovating - We solve for the customer and focus on outcomes. We are nimble in our approach. When we fail, we fail fast and learn from it. We are here to disrupt, not to fit in.
- Mindset - We are committed to a growth mindset. Our efforts and attitudes are what determine our abilities. We embrace good criticism. We seek new challenges. We never stop learning.
About Bestpass: Bestpass is a comprehensive payment platform provider and leader in toll management solutions for commercial fleets of all sizes. Bestpass saves fleets time and money by consolidating payments and providing insight into cost per vehicle. Bestpass, founded in 2001, covers 100% of major toll roads across the U.S., supports more than 30,000 customers, and processes over $1.5 billion in toll transactions annually. Bestpass offers a range of toll coverage options for owner-operators, regional fleets, and national fleets, as well as customized solutions for specific needs.
About Fleetworthy Solutions: Fleetworthy Solutions, Inc. provides DOT safety and regulatory compliance services to commercial fleets that take them Beyond Compliant. Fleetworthy combines exceptional client service, advanced technologies, and more than 40 years of transportation industry expertise to make sure that drivers and assets are truly fleetworthy. The company helps private fleets, for-hire carriers and third-party logistics companies of all sizes surpass compliance of federal, state, and local regulations and streamline processes to reduce costs and mitigate risks.
Fleetworthy is committed to fostering a diverse and inclusive culture that is respectful and welcoming of individual differences. We are proud to be an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion or belief (or lack thereof), sex, nationality, national or ethnic origin, civil status, age, citizenship status, sexual orientation, disability, genetic information, familial status, marital or registered civil partnership status, pregnancy or maternity status, gender identity, gender reassignment, military or veteran status, or any other protected characteristic in accordance with applicable laws and regulations