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Goosehead Insurance

Enterprise Retention Specialist I

Posted 5 Days Ago
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In-Office
Chicago, IL, USA
Entry level
In-Office
Chicago, IL, USA
Entry level
Entry-level retention specialist who re-markets expiring or at-risk policies, executes multi-carrier reshops, presents alternative coverage, and identifies cross-sell opportunities. Provides high-touch client service, documents interactions in agency systems, follows scripts and compliance standards, completes required training, and maintains an active state insurance license to support retention and agency revenue goals.
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The Retention Specialist I is an entry-‑level role responsible for re‑-marketing existing clients whose policies are expiring, experiencing premium increases, or facing adverse underwriting actions. This position blends sales expertise with high-‑touch service execution to ensure clients remain optimally placed with the right coverage solutions. Specialists conduct reshops, present alternative policy options, and proactively identify opportunities to cross-‑sell additional products. The role is central to preserving client relationships, stabilizing retention outcomes, and supporting agency revenue growth.

The Retention Specialist I serves as a front-line resource for clients requiring policy review, re‑marketing, or cancellation mitigation. When a client is price‑-sensitive or impacted by underwriting changes, the specialist evaluates available carrier options, reshops the policy, and presents tailored solutions that align with the client’s needs. This role requires balancing consultative sales skills with the precision and care of a service professional.

Specialists follow established workflows, scripts, and compliance standards while developing deeper insurance knowledge and autonomy. They are expected to identify cross‑-sell opportunities that enhance coverage and contribute to agency revenue. Performance is measured through retention outcomes, productivity metrics, and the ability to deliver a positive client experience during moments of potential attrition.

Job Responsibilities:

• Conduct outbound and inbound interactions with clients requiring policy reshops, renewal reviews, or cancellation mitigation
• Evaluate client needs and present alternative policy options when price sensitivity or underwriting changes occur
• Execute reshops across multiple carriers, ensuring accurate quoting and appropriate placement
• Deliver a concierge‑level service experience while applying sales techniques to retain and grow accounts
• Identify and pursue cross‑sell opportunities that enhance client coverage and agency revenue
• Document all interactions, outcomes, and next steps in agency systems
• Follow established scripts, workflows, and compliance guidelines
• Maintain active state insurance license and complete required training
• Collaborate with team members and leadership to meet retention and productivity goals

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