Cottingham & Butler
InsuranceDirect Greenhouse career site

Regional Sales Leader - Employee Benefits

Location
Des Plaines, IL · On-site
Job type
Full-time
Level
Lead / Staff
Experience
5+ years
Listed
31 days ago

Skills & highlights for this role

  • employee benefits insurance
  • sales leadership
  • carrier relationship management

Stated benefits & perks

  • Medical
  • Dental
  • Vision
  • 401k match
  • Pto

Location: Des Plaines, Illinois

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.

Key Responsibilities

  • 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.

Qualifications

  • 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.

Additional information

If you are a proven leader with a passion for sales and employee benefits, and a knack for driving team success, we want to hear from you! Apply now to join our team and lead the Des Plaines Regional Office to new heights.

Pay & Benefits

  • 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
  • and so much more!

About Cottingham & Butler

At Cottingham & Butler, we sell a promise to help our clients through life's toughest moments. To deliver on that promise, we aim to hire, train, and grow the best professionals in the industry. We look for people with an insatiable desire to succeed, are committed to growing, and thrive on challenges. Our culture is guided by the theme of "better every day" constantly pushing ourselves to be better than yesterday - that's who we are and what we believe in.

As an organization, we are tremendously optimistic about the future and have incredibly high expectations for our people and our performance. Our ability to grow as a company, fuels investments in new resources to better serve our clients and provide the amazing career opportunities our employees want and deserve. This is why we are a growth company and why we are committed to being better every day.

Want to learn more?

Read the original posting

From Cottingham & Butler's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

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Common questions

Where is the Regional Sales Leader - Employee Benefits job at Cottingham & Butler located?

This Regional Sales Leader - Employee Benefits position at Cottingham & Butler is located in Des Plaines, IL (On-site). Always check Cottingham & Butler's application page for specific state eligibility or relocation policies.

What qualifications are required for Regional Sales Leader - Employee Benefits at Cottingham & Butler?

For the Regional Sales Leader - Employee Benefits role, Cottingham & Butler highlights 5+ years of relevant experience; experience with employee benefits insurance, sales leadership, carrier relationship management. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Regional Sales Leader - Employee Benefits position at Cottingham & Butler?

This listing links directly to Cottingham & Butler's Greenhouse application page. You can apply directly on Cottingham & Butler's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Greenhouse application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.