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Regional Sales Leader - Employee Benefits

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Cottingham & Butler

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Location:
United States , Des Plaines

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Category:

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Contract Type:
Not provided

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Salary:

Not provided

Job Description:

Cottingham & Butler is seeking an Employee Benefits sales leader for our Des Plaines, Illinois office. As the Sales Manager of our regional office, you will drive profitable growth in employee benefits, spearhead sales initiatives, and deliver exceptional value to our clients. Your leadership will be pivotal in developing a high-performing team that achieves sustained success. Don’t miss your chance to be part of one of the largest and fastest growing insurance brokerages in the nation.

Job Responsibility:

  • Sales Leadership: Take charge of the regional employee benefits sales efforts, combining marketing, sales, and analytical strategies to cultivate and close business with target customers
  • Drive new business through hiring, managing, and developing sales executives
  • Attend sales calls to assist in closing deals and build strong personal relationships with sales producers
  • Strategic Vision: Execute and implement the employee benefits vision and strategy for the regional office
  • Translate this vision into actionable annual operational plans
  • Promote the identification and evaluation of new products, services, and processes to enhance practice performance
  • Client Service & Partnerships: Ensure our Employee Benefits service model exceeds client expectations and revenue retention targets
  • Review work products to meet service standards
  • Develop strong relationships with insurance carriers and partners to offer unique benefits and differentiate from competitors
  • Financial Management: Achieve growth and profitability targets for the regional office
  • Drive initiatives to improve overall financial performance, including cross-selling

Requirements:

  • 5+ years of proven experience in sales leadership within the employee benefits insurance industry
  • Strong track record of achieving sales targets and driving business growth
  • Ability to develop and mentor a high-performing sales team
  • Excellent interpersonal and communication skills
  • Strategic thinker with the ability to translate vision into action
  • Strong relationship-building skills with clients, carriers and vendors
What we offer:
  • Full annual salary and bonus opportunities
  • Most Benefits starting day one
  • Medical, Dental, Vision Insurance
  • Flex Spending or Health Savings Account
  • 401(k) with company match
  • Profit-sharing/Defined contribution (1-year waiting period)
  • PTO/Paid Holidays
  • Maternity Leave & Parental Leave

Additional Information:

Job Posted:
February 17, 2026

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