Driver Retention Supervisor

The primary purpose of this position is to oversee the driver retention team and ensure the execution of strategies designed to maintain a stable and satisfied driver fleet. This role is responsible for supervising Retention Associates, managing escalated driver concerns, and analyzing high-level retention data to drive departmental improvements. The Driver Retention Supervisor will lead a team dedicated to preserving our professional driver relationships and reducing turnover. This role combines people management with strategic analysis, overseeing daily retention operations, handling complex driver escalations, and collaborating with leadership to refine loyalty and engagement programs. Essential Job Functions: Oversee assigned retention associates, providing coaching, performance feedback, and professional development. Manage escalated driver concerns, acting as a secondary point of contact for complex issues requiring higher-level decision-making or financial incentives. Monitor team performance using CRM dashboards and KPIs to ensure outreach targets and retention goals are met. Analyze retention trends and churn data to provide actionable insights and reports to senior management. Refine and optimize retention strategies, including the development of new loyalty initiatives and driver appreciation programs. Collaborate with Department Leaders in Safety, Operations, and Recruiting to address systemic issues impacting the driver experience. Facilitate team training on negotiation techniques, conflict resolution, and new software implementations. Perform additional duties as directed by supervisors to assist in overall fleet stability and departmental growth. Knowledge, Skills & Abilities: Knowledge of Company policies, procedures, and the specific challenges faced by professional drivers. Strong leadership skills with the ability to motivate a team in a high-pressure, goal-oriented environment. Exceptional listening and negotiation skills to handle high-stakes driver interactions. Advanced proficiency in CRM software (e.g., Salesforce) and data visualization tools. Ability to communicate in a courteous and professional manner with both drivers and executive leadership. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. Education & Experience: Minimum of high school diploma or General Education Degree (GED); Bachelor’s degree in Business, Communications, or Supply Chain preferred. 3–5 years of experience in transportation, driver relations, or high-volume customer retention. Prior supervisory or lead experience is highly preferred. In-depth understanding of the transportation industry and DOT regulations is a plus. 
We know benefits are critical and we are committed to offering comprehensive and affordable options for you and your loved ones. This position is eligible for benefits, which include medical, dental and vision plans. We also offer a 401(k) plan, stock purchase plan, paid time off, life insurance, disability plans and other optional supplemental coverage. Werner Enterprises provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, marital status, genetic information or veteran status or other status protected by law. We encourage applicants of all ages as we do not discriminate on the basis of an applicant's age. By clicking “Submit” you are expressly consenting to our Privacy Policy (available at https://www.werner.com/privacy-policy/) and to Werner Enterprises, Inc., its representatives, and affiliates (“Werner”) contacting you about your inquiry, and that Werner may collect sensitive information about you to consider your employment as explained further in our Privacy Policy. All information collected will be handled and retained as explained in the Privacy Policy.