Customer Success Manager - SMB

Fleetworthy offers the only complete technology suite for fleet readiness, uniting safety and compliance, toll management, and weigh station bypass solutions. We help fleets streamline operations, control costs, and operate with confidence.

Trusted by 75% of the top fleets in North America, Fleetworthy offers the most adopted toll management solution and largest weigh station bypass network. Going beyond regulatory requirements, our safety and compliance capabilities strengthen safety programs and enable proactive audit readiness. We support millions of vehicles and drivers and are recognized across the industry for innovation and leadership.

Fleetworthy is shaping the future of fleet readiness with AI-enabled, connected fleet technology that keeps drivers safe, fleets compliant, and operations running at peak efficiency. Learn more at fleetworthy.com.

Role Summary:

The Scaled Customer Success Manager (CSM) for SMB accounts is an individual contributor in the Customer Experience organization, charged with driving scalable engagement across a large portfolio SMB customers. This role combines strategic program execution with automation, proactive outreach, and data-informed decision-making to improve customer health, increase retention, identify expansion opportunities, and cultivate brand advocates.

Essential Duties and Responsibilities:

• Develop and execute strategic email campaigns and outreach sequences (personalized and automated).

• Build and optimize workflows using our Customer Success platform.

• Analyze account data to generate customized insights for clients at scale and prioritize actions.

• Facilitate one-to-many engagement efforts (webinars, office hours, etc.).

• Collaborate cross-functionally with Product, Sales, Marketing and Support to drive customer value.

• Engage with customers 1:1 where appropriate to drive product adoption, expansion opportunities or resolve escalated issues.

Success Metrics:

The success of this role will be defined by the ability to foster engagement with clients at scale while driving the following positive outcomes among the assigned SMB book of business:

• Gross Revenue Retention (GRR) & Net Revenue Retention (NRR)

• Campaign engagement (open rates, CTRs)

• Volume of case study/reference wins

• Churn reduction

• Qualified leads for account expansion generated

• Customer reviews (Google, Trustpilot)

Requirements:

• Bachelor’s degree in Business, Communications or a related field

• 2+ years in Customer Success, Account Management or in a similar client-facing role preferred

• Strong written and verbal communication and data analysis skills

• Proficient in Microsoft Excel, PowerPoint and Word

• Excellent problem solving and relationship building skills

• Comfortable working both autonomously and cross-functionally (product, sales, support, marketing) to solve client issues

• Familiarity with CRM systems like Salesforce, Planhat, or Gainsight preferred

• Previous experience in the transportation industry is a plus, but not required

Please note this job description is not designed to cover or contain a comprehensive listing of task activities and/or duties that are required of the employee for this job. Responsibilities and activities may change at any time with or without notice.

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.