Driver Success and Retention Manager

Driver Success & Retention Manager

Ashburn, VA (In-Office)
Full-Time | Monday–Friday supporting 24/7/365 operation

Overview

We are hiring a Driver Success & Retention Manager to own the relationship, engagement, and retention of our independent contractor driver network.

This role is responsible for ensuring drivers are activated quickly, supported consistently, and retained long-term. You will work closely with Dispatch and Operations to keep drivers engaged, productive, and aligned with expectations.

Key Responsibilities

• Own the driver relationship from post-orientation through ongoing engagement


• Ensure new driver activation and early success (first 7/14/30 days)


• Coach drivers on performance, service standards, and expectations


• Partner with Dispatch to ensure driver utilization and engagement


• Resolve driver issues including settlement discrepancies and communication gaps


• Identify and address retention risks and disengagement trends


• Maintain consistent driver communication and follow-up


• Collaborate with Recruiting, Dispatch, and Operations for alignment


• Track and improve driver retention and engagement metrics


• Use systems and data to identify gaps and improve processes

Qualifications

• Experience working with independent contractors, field teams, or service-based workforce


• Strong communication and relationship-building skills


• Experience resolving performance, service, or operational issues


• Ability to work in a fast-paced, high-volume environment


• Strong problem-solving skills and initiative


• Comfortable using technology platforms and systems


• Experience in logistics, transportation, or courier operations preferred

What We’re Looking For

• High sense of ownership and accountability


• Ability to ask questions, push for clarity, and solve problems


• Strong follow-through and urgency


• Comfortable handling difficult conversations


• Ability to work cross-functionally and influence outcomes

Work Environment

• In-office role with frequent communication via phone, text, email, and in-person


• Fast-paced operational setting


• Occasional travel to customer or company locations


• Ability to lift up to 50 lbs. and work in office/warehouse environments

Compensation & Benefits

• Competitive salary


• Health, dental, and vision insurance


• 401(k)


• Paid time off

Why Apply

This is a high-impact role directly tied to driver performance, retention, and overall service quality. If you’re looking for a position where you can own outcomes and improve operations, apply today.