Senior Renewals & Retention Strategist

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: 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. Market risks to carriers as needed to negotiate improved pricing or coverage. 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. Develop and maintain dashboards for transparency, performance visibility, and accountability. Provide ongoing training to: Renewal agents, Customer service representatives, and Sales agents on renewal positioning and closing Create scripts, objection‑handling guides, and closing frameworks. Coordinate 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. Knowledge, Skills, and Abilities (KSA’s): 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. 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. 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. 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. Sales & Negotiation Abilities — Skilled in objection handling, persuasive communication, upselling, cross‑selling, and negotiating renewal terms to achieve revenue and retention goals. 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. 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. 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. Problem‑Solving & Critical Thinking Skills — Adept at identifying issues, evaluating options, resolving complex client challenges, and developing strategic retention solutions. 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. 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: 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 2 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. #J-18808-Ljbffr Prestige Trucking Insurance