Outside Sales Manager Business Insurance

Job Title: Outside Sales – Business Insurance

Company: The Chamberlain Agency

Location: Brookfield, WI (Hybrid)

Employment Type: Full-Time

Compensation and Benefits:

• On-Target Earnings (OTE): $50,000–$100,000 (commission-based with performance bonuses)
• Flexible  schedule 
• Professional development
• Leadership and advancement opportunities
• Recognition trips and incentive programs
• Supportive team culture with a growth mindset

Company Description

The Chamberlain Agency is a fast-growing insurance firm dedicated to helping businesses protect their people and operations. We provide tailored insurance solutions and believe in developing long-term client relationships while empowering our agents with tools and training for success.

Role Description

We are seeking a driven and professional Outside Sales Representative specializing in Business Insurance to serve clients in and around Brookfield, WI. This  role offers some  flexibility while focusing on B2B sales, insurance consulting, and account development. You’ll work directly with business owners and HR teams to deliver customized insurance solutions that protect their employees and operations.

Key Responsibilities

• Prospect and engage small to mid-sized businesses to assess their insurance needs
• Sell life and supplemental insurance products as part of comprehensive employee benefit solutions
• Build and maintain strong, consultative relationships with decision-makers
• Educate clients on policy options, compliance requirements, and claims processes
• Achieve or exceed monthly sales goals while maintaining detailed client records
• Stay up to date on industry regulations and product offerings
• Partner with internal teams to ensure client satisfaction and retention

Qualifications

• Experience in outside sales, B2B insurance, or financial services preferred
• Strong communication, consultative selling, and relationship-building skills
• Ability to explain insurance concepts in a clear and compelling way
• Detail-oriented with excellent time management and problem-solving abilities
• Self-motivated and results-driven
• Knowledge of insurance products and commercial insurance compliance
• Must obtain a state insurance license before starting (no college degree required)

Alternate Titles:

• Business Insurance Sales Representative
• Commercial Insurance Agent
• B2B Outside Sales Consultant
• Insurance Sales Executive
• Employee Benefits Sales Specialist

Keywords:

Business insurance, commercial insurance, outside sales, B2B sales, licensed insurance agent, employee benefits, insurance producer, hybrid sales role, Brookfield WI jobs, insurance sales, small business coverage, commercial policies, commission-based sales, client relationship management, insurance brokerage.