Renewals and Retention Specialist

Position Summary

Prestige Trucking Insurance seeks a Renewals and Retention Specialist to lead the agency's renewals department and protect and grow its book of business. This role involves managing retention outcomes, cancellation reduction, and year-over-year premium growth, making it suitable for someone who excels in both client relationships and team leadership.

About the Role

The role encompasses the entire renewal lifecycle, from identifying at-risk accounts to executing retention strategies, negotiating with underwriters, managing cancellation-prevention workflows, and overseeing the 90/60/30-day communication cadence. It also includes leading and developing the renewals team, conducting coaching sessions, building Standard Operating Procedures (SOPs), and collaborating cross-functionally with various teams.

Essential Duties and Responsibilities

• Help oversee all renewal accounts and agency-wide retention initiatives.
• Implement strategies to maintain a minimum 85% retention, with a target of 95%+ retention ratio.
• Proactively identify at-risk accounts and create tailored recovery plans.
• Personally intervene on high-value, complex, or escalated accounts to secure renewal.
• Develop and manage cancellation-prevention workflows.
• Track and reduce mid-term cancellations through proactive outreach.
• Delegate and distribute renewal assignments strategically for workload balance and efficiency.
• Maintain accountability using performance metrics, dashboards, and daily activity tracking.
• Conduct weekly retention performance meetings and coaching sessions.
• Train team members in objection handling, closing strategies, and retention best practices.
• Develop and maintain SOPs for renewal processes and retention workflows.
• Increase department book value by at least 20% annually.
• Identify and execute on cross-sell and upsell opportunities during renewal conversations.
• Ensure proper marketing of risks to secure competitive carrier terms.
• Collaborate with Underwriting and Marketing to strengthen pricing leverage.
• Help oversee remarketing processes for non-renewals or accounts needing improved terms.
• Negotiate renewal terms directly with underwriters.
• Maintain strong relationships with carrier partners to support retention and competitive positioning.
• Help monitor account loss ratios and coordinate risk-mitigation strategies.
• Ensure a superior customer experience throughout the renewal cycle.
• Develop and implement standardized renewal scripts, service protocols, and communication guidelines.
• Oversee the 90/60/30-day renewal communication cadence across the team.
• Conduct client audits when needed to eliminate exposure gaps and strengthen retention.
• Monitor and report key retention KPIs, including: Retention Ratio (Goal: 95%+), Cancellation Rate, Renewal Conversion Rate, Premium Retained, Revenue Growth (20% YoY target), Cross-Sell Ratio, and Save Rate on Cancellations.
• Provide weekly and monthly retention/renewal reports to executive leadership.
• Create scripts, objection-handling guides, and closing frameworks.
• Collaborate with Marketing on renewal-generated leads and retention-focused campaigns.
• Manage the flow of referrals generated during renewal conversations.
• Collaborate with Sales to identify book optimization and revenue opportunities.
• Ensure smooth handoff and communication between New Business, Service, and Retention teams.
• Partner with the Service team to enhance client experience, reduce cancellations, and drive cross-sell opportunities.

Key Performance Indicators (KPIs)

• Retention Rate: Maintain a minimum retention rate of 85%, with a strategic target of 95% or higher across the renewal portfolio.
• Annual Book Growth: Achieve 20% year-over-year growth within the retention department through renewal success, upselling, and cross-selling initiatives.
• Cancellation Reduction: Demonstrate measurable decreases in mid-term and renewal-related cancellations through proactive outreach and save strategies.
• Cross-Sell Performance: Increase cross-sell revenue and improve the overall cross-sell conversion rate during renewal interactions.
• Customer Satisfaction: Drive continuous improvement in customer satisfaction scores through enhanced service quality and client experience.
• Workflow Compliance: Ensure consistent adherence to all renewal workflows, communication cadences, SOPs, and compliance standards.

Minimum Qualifications

• Bachelor’s degree in Business, Marketing, Communications, Insurance, or a related field; or equivalent work experience in customer success, retention, or account management.
• Active Florida 20 General Lines Insurance License.
• Minimum 3-5 years of experience in customer success, account management, renewals, or retention-focused roles.
• Experience within the insurance industry or a similar regulated field preferred.
• Minimum 2 years of team leadership, supervisory, or coaching experience, preferably in a retention, customer success, or sales environment.
• Working knowledge of insurance renewal workflows, underwriting basics, risk evaluation, and carrier relations (or ability to learn these quickly).
• Strong verbal and written communication skills, with the ability to explain complex information clearly and professionally.
• Demonstrated ability to handle escalations, difficult conversations, and conflict resolution.
• Proven ability in upselling, cross-selling, objection handling, and negotiating terms or pricing.
• Ability to analyze KPIs, identify trends, interpret customer data, and present insights to leadership.
• Proficiency with CRM systems, agency management systems (AMS), and Microsoft Office Suite (Excel, Outlook, Teams, etc.).
• Comfortable learning new tools and working within structured workflows.
• Ability to manage multiple priorities, deadlines, and renewal timelines simultaneously.
• Active insurance license (Property & Casualty) or willingness to obtain one within company-defined timeframes.

Physical Demands and Work Environment

Requires extended periods of sitting, computer use, and handling digital documents, along with clear communication via phone and video. Professional office work setting with standard office equipment and moderate noise levels. Fast-paced, deadline-driven environment with frequent collaboration across departments. Requires handling confidential client information in compliance with privacy and security standards.