Strategic Lead Customer Service Representative

Job Description

Job Description

Position Summary:

Prestige Trucking Insurance is seeking a Strategic Lead Customer Service Representative (CSR) / Assistant Customer Service Manager to help lead its insurance servicing function. The Lead Customer Service Representative / Assistant Customer Service Manager works closely with operations, finance, and sales to optimize the service experience for our customers. The ideal candidate will bring a blend of technical expertise, operational leadership, and a proactive mindset. The Strategic Lead Customer Service Representative (CSR) / Assistant Customer Service Manager is a key leadership role within Prestige, responsible for overseeing the Customer Service team, supporting high-volume client accounts, and serving as the primary trainer for all new service hires across Prestige, including US-based and remote team members. This position combines strategic growth, team leadership, client service management, and comprehensive training responsibilities. The ideal candidate is an experienced insurance professional with deep knowledge of trucking and commercial auto insurance, excellent problem-solving skills, and the ability to balance leadership responsibilities with hands-on support. The exact job grading will be commiserate with the candidates experience. The role is preferably on site but can be remote for the right individual.

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.
• 2-20 Property and Casualty License

Physical Demands & Work Environment:

• Office based role with extended periods of computer and phone use
• Professional office environment with moderate noise levels
• Fast-paced, deadline-driven environment with real-time problem-solving.
• Standard business hours with occasional extended hours during renewal or peak servicing periods. May involve extended hours, rotating shifts, or weekend coverage during peak periods.
• Frequent interaction with internal teams, carriers, and insured clients via phone and electronic communication
• May involve virtual or in person meetings as needed