New Job Opening: Insurance Sales Executive - Employee Benefits in Milwaukee, WI

Job Description

Insurance Sales Executive – Employee Benefits

Job Summary

Seeking high-performing, entrepreneurial Insurance Sales Executives to drive aggressive growth in the Midwest region. This role is ideal for professionals who thrive on autonomy, ownership, and the opportunity to build a successful career in a producer-led organization. If you are a motivated sales professional with a proven track record or the grit to succeed in a high-performance environment, want to hear from you.

Compensation Package

• Draw-Based Model: Compensation is structured on a draw equivalent to 25% of annual production potential. For example, a $300,000 base pay corresponds to $1.2M in annual production.


• Transition Period: Optional 1–2 year W2 transition period available, if needed.


• Long-Term Upside: Full partner economics over time, with significant flexibility in income allocation.


• Average Producer Book: ~$5M in revenue, with strong earning potential.

Responsibilities

• Generate new, qualified business through self-directed methods.


• Build and grow a long-term, high-quality book of business.


• Collaborate with a Unit Manager to allocate resources and manage growth effectively.


• Leverage dedicated service and associate teams for client servicing and execution.


• Strategically reinvest in business development, client engagement, and service excellence.

Qualifications/Requirements

• Proven track record as a high-performing producer with strong sales capabilities.


• Entrepreneurial mindset with a comfort level for financial risk and a drive for growth.


• Ability to operate with minimal top-down constraints and thrive in an autonomous environment.


• Strong cultural alignment with a producer-led organization.


• Open to candidates with non-insurance backgrounds who demonstrate exceptional sales acumen and resilience (e.g., former professional or collegiate athletes, military academy graduates, or individuals with similar high-performance backgrounds).


• Willingness to engage in a thorough vetting and evaluation process.

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