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Entry Level Sales Executive - Employee Benefits

United States, Madison · Job Posted February 17, 2026
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Job Description

Cottingham & Butler is actively looking for ambitious and driven entry-level Sales Executives in our Madison, Wisconsin location! Seeking all sales minded, soon-to-be college graduates, recent college graduates, or individuals with 1-3 years of sales experience who are motivated by financial rewards. We are consultants, not just insurance shoppers. In addition to designing employee benefits packages, we help with strategic planning, analytics, cost containment, regulatory and compliance issues, and M&A/ due diligence, etc.

Job Responsibility

  • Learn the business and become a trusted advisor to company leaders
  • Identify, qualify, and close prospects
  • Manage and retain your book of business and actively work towards its growth to unlock substantial financial growth
  • Strategize and develop customized solutions for clients, leveraging available programs to deliver services that exceed client expectations
  • Cultivate strong relationships with top decision makers, ensuring long-term client retention
  • Collaborate with our service team to create compelling proposals and deliver impactful presentations to clients and prospects
  • Earn relevant designations and stay up-to-date on continuing education credits provided by the company to enhance your professional growth and earning potential

Requirements

  • Ambitious and driven
  • Sales minded
  • Soon-to-be college graduate, recent college graduate, or individuals with 1-3 years of sales experience
  • Motivated by financial rewards
  • Thrive in a fast-paced, competitive environment
  • Possess a relentless drive for success
  • Insatiable desire to succeed
  • Committed to growing
  • Thrive on challenges

What we offer

  • Comprehensive training
  • Unparalleled service support
  • Unique resources
  • Necessary tools
  • Access to experienced Account Management Teams
  • Access to in-house specialists in compliance, HR consulting, analytics, client communications, worksite products, stop loss and technology
  • Access to tools & resources such as assessments, checklists, audits
  • Access to partner companies providing additional resources such as ThinkHR and Zywave

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