Outside Sales Agent

Outside Sales Insurance Manager Brookfield WI (Hybrid)

Ready to earn what youre truly worth and build a career with purpose flexibility and unlimited potential The Chamberlain Agencies is looking for driven motivated individuals to join our fast-growing sales team and make a real difference in the lives of working families and local businesses.

Why This Role Stands Out:

• Uncapped Commission Monthly Bonuses
• $50K - $100K First-Year Potential
• Training Pay Provided
• Career Advancement in 26 Months
• Warm Leads & Salesforce CRM Included
• Hybrid Schedule: Mondays in Office Rest Remote/Local Travel

About the Role:

As an Outside Sales Manager youll be the face of The Chamberlain Agencies. Youll work directly with local business owners to help their employees access affordable life and supplemental benefits at zero cost to the employer.

Your responsibilities will include:

• Building and maintaining strong business relationships
• Meeting with employers and employees to explain and enroll them in their benefits
• Managing your pipeline using Salesforce CRM
• Collaborating with leadership on strategy performance and client success

This is a 1099 commission-only opportunity ideal for professionals who thrive in a performance-based entrepreneurial environment.

Who This is For:

Were looking for candidates who are:

• Self-motivated competitive and coachable
• Capable of managing their time and pipeline independently
• Licensed or willing to become licensed in the state of Wisconsin
• In possession of a valid drivers license and reliable vehicle
• Able to pass a background check (no felony convictions)
• Comfortable working MF full time with Mondays in-office in Brookfield

If youre not comfortable in a commission-based environment or unable to work locally in the Brookfield WI area this role may not be the right fit.

What Makes The Chamberlain Agencies Different

Were not just another insurance agency. Our mission is to deliver affordable high-value benefits that protect families and empower business owners all with personalized service and zero employer cost.

At our core we believe in:

• Promoting from within (every leader started in sales)
• Paying people based on what they produce not time on the clock
• Giving our team the training leads and tools they need to win and grow fast

If youre hungry for more more freedom more income more meaning we want to meet you.

Ready to Build Something Big

If youre ready to take control of your income grow your career and make an impact apply now. This is more than a job. Its a pathway to leadership financial freedom and a community that backs your success.

Apply today and take the first step toward your future with The Chamberlain Agencies.

We are an Equal Opportunity recruiter and welcome applicants from all backgrounds without regard to race color religion sex sexual orientation gender identity national origin disability or protected veteran status. We may use automated tools including artificial intelligence (AI) to screen and assess candidates as part of our hiring process. These tools are used to support and not replace human decision-making.

By applying you consent to the collection and use of your personal information for recruitment purposes in accordance with applicable data protection laws based on your location. Employment may be at-will depending on state law and the employers terms. For 1099 opportunities applicants are considered independent contractors and not employees. If you require accommodation during the application or interview process please contact us directly. All applications are kept confidential.

Job Type: Full-time

Pay: $59400.67 - $93579.30 per year

Benefits:

• Work from home

Compensation Package:

• Commission pay

Schedule:

• 8 hour shift

Application Question(s):

• Do you already have or are willing to obtain an insurance sales license

License/Certification:

• Drivers license and Reliable Vehicle (Required)

Ability to Commute:

• Brookfield Wisconsin 53005 (Required)

Work Location: Hybrid remote in Brookfield Wisconsin 53005