Strategic Lead Customer Service Representative

Position Summary

Prestige Trucking Insurance seeks a Strategic Lead Customer Service Representative (CSR) / Assistant Customer Service Manager to lead its insurance servicing function. The ideal candidate will bring a blend of technical expertise, operational leadership, and a proactive mindset.

Essential Duties and 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

Knowledge, Skills, and Abilities (KSA’s)

• Leadership & Team Support — Serves as a resource and mentor to CSRs; supports consistent service execution
• Strong leadership, mentoring, and team development abilities
• Commercial Trucking Insurance Expertise — Strong understanding of trucking coverages, servicing workflows, and carrier requirements
• Problem Solving & Judgment — Resolves escalated issues effectively and knows when to involve management or producers
• Attention to Detail — Ensures accuracy in policy changes, certificates, endorsements, and documentation
• Communication Skills — Communicates clearly and professionally with clients, carriers, and internal teams
• Time Management & Organization — Manages multiple priorities while meeting turnaround and SLA expectations
• Professionalism & Integrity — Handles sensitive client information with discretion and reliability

Minimum Qualifications

• High school diploma or GED required; Associate’s or Bachelor’s degree preferred
• 2–5 years of commercial/trucking insurance experience
• Prior leadership or senior CSR experience highly desirable
• Experience managing high-volume client accounts, including books of business exceeding $300K, preferred
• Experience in training, onboarding, or mentoring employees is strongly preferred