Welcome to Bet On You LLC, an Allstate Insurance Agency. We empower our community and protect our tomorrow. We are a passionate, competitive, and highly motivated team that thrives on the success of each other and the success of our customers. Our employee and customer centered culture provides an excellent experience in every interaction.

The Retention & Winback Specialist plays a key role in maintaining client loyalty and re-engaging former customers. This position is responsible for proactively managing client relationships, addressing coverage concerns, resolving issues, and implementing targeted outreach to retain current policyholders and recover lapsed accounts.

Salary Range: $35,000.00 - $60,000.00 per year

Benefits

Annual Base Salary + Commission

Paid Time Off (PTO)

Flexible Schedule

Hands on Training

Mon-Fri Schedule

Career Growth Opportunities

• 2+ years of experience in insurance, customer retention, account management, or sales.
• Active insurance license
• Strong communication and interpersonal skills with a customer-first mindset.
• Proven ability to manage objections and negotiate solutions.
• Goal-oriented with experience meeting or exceeding retention or sales targets.
• Proficiency in CRM software and Microsoft Office Suite.
• High attention to detail and ability to work independently.

• Retain existing clients by delivering exceptional service, anticipating needs, and resolving concerns before renewal.
• Proactively identify cross-selling opportunities by analyzing client policies, lifestyle changes, and risk profiles.
• Recommend complementary products to strengthen protection and increase policy value.
• Use consultative sales techniques to explain product benefits, demonstrate cost savings through bundling, and align solutions with client priorities.
• Monitor upcoming renewals and coverage changes to present timely offers that expand client portfolios.
• Manage and optimize winback outreach flows to re-engage lapsed or canceled policyholders.
• Track and report on retention, cross-sell and recovery performance metrics.
• Maintain accurate client records and follow-up actions in the CRM.
• Collaborate with sales and service teams to refine strategies and improve results.

Welcome to an Insurance Agency. We empower our community and protect our tomorrow. We are a passionate, competitive, and highly motivated team that thrives on the success of each other and the success of our customers Our employee and customer centered culture provides an excellent experience in every interaction.