[Remote] Strategic Lead Customer Service Representative

Note: The job is a remote job and is open to candidates in USA. Prestige Trucking Insurance is seeking a Strategic Lead Customer Service Representative to help lead its insurance servicing function. This key leadership role is responsible for overseeing the Customer Service team, supporting high-volume client accounts, and serving as the primary trainer for all new service hires.

Responsibilities

• Audit and redefine best practices for service
• Strategically lead and own the KPIs around service delivery
• Monitor departmental KPIs including response time, accuracy, and client satisfaction
• Assist in managing the Service Inbox (Service Box) and ensure timely and accurate task completion
• Oversee the COI Department to ensure timely processing and address escalations or special requests
• Support the CAB Reports process, ensuring proper follow-ups and compliance
• Identify and recommend process improvements and workflow enhancements
• Ensure all documentation and client records meet agency, carrier, and regulatory standards
• Assist with internal audits, quality assurance reviews, and compliance processes
• Provide guidance, coaching, and support to Customer Service Representatives and Account Managers
• Serve as a point of contact for team members’ questions, queries, and escalations
• Assist in resolving complex or disgruntled client issues professionally and efficiently
• Support the Customer Service Manager and Director of Operations in any areas needed, including reporting or administrative projects
• Serve as acting manager in the absence of the Customer Service Manager, including conducting departmental meetings, monitoring performance, and maintaining productivity standards
• Foster a positive, collaborative, and accountable work culture, leading by example
• Ensure compliance with company procedures, regulatory requirements, and service standards
• Establish best practices for providing high quality client support
• Provide operational and service support for high-volume and large client accounts
• Handle complex client inquiries, escalations, and service-related issues
• Ensure accurate processing of Certificates of Insurance (COIs), endorsements, coverage changes, cancellations, and reinstatements
• Maintain organized, compliant, and up-to-date client records, emails, and documentation in agency management systems
• Collaborate with MGAs, carriers, and internal departments to facilitate timely and effective resolution of client requests
• Conduct comprehensive onboarding and training programs for all new service hires across Prestige, including US-based and remote team members
• Responsible for training all Customer Service and Service Department new hires, assisting with their onboarding, and ensuring they understand workflows, procedures, compliance requirements, and agency standards
• Monitor and evaluate trainee performance, documenting progress and readiness for team placement
• Provide detailed reports on each trainee’s performance, strengths, and areas for development to the Customer Service Manager prior to transferring employees to their respective teams
• Continuously improve training materials and methods to maintain consistency, quality, and operational efficiency across all teams

Skills

• High school diploma or GED required
• 2–5 years of commercial/trucking insurance experience
• Prior leadership or senior CSR experience highly desirable
• 2-20 Property and Casualty License
• Strong leadership, mentoring, and team development abilities
• Strong understanding of trucking coverages, servicing workflows, and carrier requirements
• Resolves escalated issues effectively and knows when to involve management or producers
• Ensures accuracy in policy changes, certificates, endorsements, and documentation
• Communicates clearly and professionally with clients, carriers, and internal teams
• Manages multiple priorities while meeting turnaround and SLA expectations
• Handles sensitive client information with discretion and reliability
• Associate's or Bachelor's degree preferred
• Experience managing high-volume client accounts, including books of business exceeding $300K, preferred
• Experience in training, onboarding, or mentoring employees is strongly preferred

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