Entry Level Enterprise Sales Specialist Jobs

About Goosehead

Since 2003, Goosehead Insurance has been disrupting the insurance industry by giving clients the power of choice, utilizing a smarter marketing approach, and delivering world class service. This is all powered by our focus on hiring and retaining extraordinary people. Our clients trust us with their most valuable possessions so, we’re more than just a bit selective when it comes to hiring new team members.

Job Summary

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.

Principal Duties And 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

Role Requirements

• Property & Casualty Insurance License
• Legally authorized to work the United States

Required Skills And Abilities

• Experience with managing customer relationships
• Experience with CRM systems
• Team-oriented
• Entrepreneurial spirit
• Problem-solving mentality

Compensation Summary

This position has a base salary of $48k in addition to a highly competitive commission structure.

Benefits Summary

• High-quality voluntary health, vision, disability, life, and dental insurance programs.
• 401K Matching Plan.
• Employee Stock Purchase Plan.
• Paid holidays, vacation, and sick leave.
• Corporate sponsored programs to enhance employee physical, financial, mental, and emotional wellness.
• Financial Solution Program.

Equal Employment Opportunity

Goosehead is an equal opportunity employer and complies with all applicable federal, state, and local laws, rules, guidelines, and regulations. Goosehead strictly prohibits and does not tolerate unlawful discrimination against employees, applicants, or any other covered person because of race, color, religion, creed, national origin, ancestry, ethnicity, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender, gender identity, transgender status, age, physical or mental disability, veteran status, uniformed service, genetic information, or any other characteristic protected by applicable law. All applicants for employment and all Goosehead employees are given equal consideration based solely on job-related factors, such as qualifications, experience, performance, and availability.

To learn more about our job opportunities, apply here. We look forward to speaking with you!