Position Summary:
Prestige Trucking Insurance is seeking a Renewals and Retention Specialist to lead the agency’s renewals department and take direct ownership of protecting and growing its book of business. This is a role with measurable impact — the person in this position is accountable for retention outcomes, cancellation reduction, and year-over-year premium growth, making it a strong fit for someone who is equally comfortable managing client relationships and leading a team. The role spans the full renewal lifecycle — from proactively identifying at-risk accounts and executing retention strategies to negotiating with underwriters, managing cancellation-prevention workflows, and overseeing the 90/60/30-day communication cadence. In addition to day-to-day renewal management, the Renewals and Retention Specialist leads and develops the renewals team, conducts coaching sessions, builds SOPs, and collaborates cross-functionally with underwriting, sales, marketing, and service teams to ensure a seamless client experience. The ideal candidate brings a background in insurance renewals or account retention, strong leadership and communication skills, and the analytical mindset to track KPIs and continuously improve department performance.
Essential Duties and Responsibilities:
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Help oversee all renewal accounts and agency‑wide retention initiatives.
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Implement strategies to maintain a minimum 85% retention, with a target of 95%+ retention ratio.
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Proactively identify at‑risk accounts and create tailored recovery plans.
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Personally intervene on high‑value, complex, or escalated accounts to secure renewal.
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Develop and manage cancellation‑prevention workflows.
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Track and reduce mid‑term cancellations through proactive outreach.
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Delegate and distribute renewal assignments strategically for workload balance and efficiency.
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Maintain accountability using performance metrics, dashboards, and daily activity tracking.
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Conduct weekly retention performance meetings and coaching sessions.
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Train team members in objection handling, closing strategies, and retention best practices.
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Develop and maintain SOPs for renewal processes and retention workflows.
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Increase department book value by at least 20% annually.
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Identify and execute on cross‑sell and upsell opportunities during renewal conversations.
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Ensure proper marketing of risks to secure competitive carrier terms.
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Collaborate with Underwriting and Marketing to strengthen pricing leverage.
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Help oversee remarketing processes for non‑renewals or accounts needing improved terms.
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Market risks to carriers as needed to negotiate improved pricing or coverage.
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Negotiate renewal terms directly with underwriters.
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Maintain strong relationships with carrier partners to support retention and competitive positioning.
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Help monitor account loss ratios and coordinate risk‑mitigation strategies.
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Ensure a superior customer experience throughout the renewal cycle.
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Develop and implement standardized renewal scripts, service protocols, and communication guidelines.
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Oversee the 90/60/30‑day renewal communication cadence across the team.
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Conduct client audits when needed to eliminate exposure gaps and strengthen retention.
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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
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Provide weekly and monthly retention/renewal reports to executive leadership.
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Develop and maintain dashboards for transparency, performance visibility, and accountability.
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Provide ongoing training to: Renewal agents, Customer service representatives, and Sales agents on renewal positioning and closing
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Create scripts, objection‑handling guides, and closing frameworks.
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Coordinate with Marketing on renewal‑generated leads and retention‑focused campaigns.
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Manage the flow of referrals generated during renewal conversations.
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Collaborate with Sales to identify book optimization and revenue opportunities.
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Ensure smooth handoff and communication between New Business, Service, and Retention teams.
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Partner with the Service team to enhance client experience, reduce cancellations, and drive cross‑sell opportunities.
Key Performance Indicators (KPIs):
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Retention Rate: Maintain a minimum retention rate of 85%, with a strategic target of 95% or higher across the renewal portfolio.
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Annual Book Growth: Achieve 20% year-over-year growth within the retention department through renewal success, upselling, and cross‑selling initiatives.
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Cancellation Reduction: Demonstrate measurable decreases in mid‑term and renewal‑related cancellations through proactive outreach and save strategies.
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Cross‑Sell Performance: Increase cross‑sell revenue and improve the overall cross‑sell conversion rate during renewal interactions.
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Customer Satisfaction: Drive continuous improvement in customer satisfaction scores through enhanced service quality and client experience.
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Workflow Compliance: Ensure consistent adherence to all renewal workflows, communication cadences, SOPs, and compliance standards.
Knowledge, Skills, and Abilities (KSA’s):
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Customer Retention & Renewal Knowledge — Demonstrates a strong understanding of retention strategies, renewal workflows, client lifecycle management, and best practices for reducing churn and increasing long-term customer value.
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Insurance & Risk Management Knowledge — Possesses working knowledge of insurance products, underwriting considerations, carrier guidelines, risk evaluation, and the remarketing process to support effective renewal negotiation and retention outcomes.
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Customer Relationship Management Skills — Exhibits the ability to build trust, strengthen client relationships, and deliver a superior customer experience through empathy, active listening, and solution‑driven communication.
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Analytical & Data Interpretation Skills — Able to interpret retention metrics, identify trends, assess at-risk accounts, and make data‑driven decisions to improve performance and forecast retention outcomes.
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Sales & Negotiation Abilities — Skilled in objection handling, persuasive communication, upselling, cross‑selling, and negotiating renewal terms to achieve revenue and retention goals.
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Leadership & Team Development Skills — Demonstrates the ability to lead, coach, and motivate a team, establish performance expectations, conduct training, and foster a culture of accountability and continuous improvement.
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Operational & Process Management Knowledge — Understands how to create, implement, and manage SOPs, renewal workflows, compliance standards, communication cadences, and process improvements that support efficiency and consistency.
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Cross‑Functional Collaboration Abilities — Works effectively with underwriting, marketing, sales, and service teams to align strategies, resolve issues, and coordinate multi‑departmental efforts that support renewal success.
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Problem‑Solving & Critical Thinking Skills — Adept at identifying issues, evaluating options, resolving complex client challenges, and developing strategic retention solutions.
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Communication & Interpersonal Abilities — Demonstrates clear, professional communication (verbal and written), strong interpersonal skills, and the ability to convey complex information in a client‑friendly manner.
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Time Management & Organizational Skills — Capable of managing multiple renewal timelines, client follow‑ups, performance reviews, and reporting duties while maintaining accuracy, prioritization, and attention to detail.
Minimum Qualifications:
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Bachelor’s degree in Business, Marketing, Communications, Insurance, or a related field; or equivalent work experience in customer success, retention, or account management.
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Active Florida 2 20 General Lines Insurance License
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Minimum 3–5 years of experience in customer success, account management, renewals, or retention‑focused roles.
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Experience within the insurance industry or a similar regulated field preferred.
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Minimum 2 years of team leadership, supervisory, or coaching experience, preferably in a retention, customer success, or sales environment.
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Working knowledge of insurance renewal workflows, underwriting basics, risk evaluation, and carrier relations (or ability to learn these quickly).
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Strong verbal and written communication skills, with the ability to explain complex information clearly and professionally.
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Demonstrated ability to handle escalations, difficult conversations, and conflict resolution.
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Proven ability in upselling, cross‑selling, objection handling, and negotiating terms or pricing.
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Ability to analyze KPIs, identify trends, interpret customer data, and present insights to leadership.
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Proficiency with CRM systems, agency management systems (AMS), and Microsoft Office Suite (Excel, Outlook, Teams, etc.).
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Comfortable learning new tools and working within structured workflows.
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Ability to manage multiple priorities, deadlines, and renewal timelines simultaneously.
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Active insurance license (Property & Casualty) or willingness to obtain one within company‑defined timeframes.
Physical Demands and Work Environment:
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Requires extended periods of sitting, computer use, and handling digital documents, along with clear communication via phone and video.
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Professional office work setting with standard office equipment and moderate noise levels.
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Fast-paced, deadline-driven environment with frequent collaboration across departments.
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Requires handling confidential client information in compliance with privacy and security standards.
