Regional Sales Leader - Employee Benefits
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LocationDes Plaines, IL, Madison, WI, Des Plaines, Illinois, United States
Work modeon-site
Typefull-time
SeniorityLead
Experience5+ yrs
DepartmentBenefits Sales
Company size501–1,000 people
PostedJun 19, 2025 · 1y ago
Verified live4d ago
May no longer be actively hiring
Posted by the company on Jun 19, 202596% of this company's open roles have been listed for 90+ days
At a glanceSummarised by Seekless from the posting.
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
Benefits
Health insurance
Dental insurance
Vision insurance
Flexible spending account
Health savings account
401(k)
Profit sharing
PTO
Paid holidays
Maternity leave
Parental leave
Regional Sales Leader, Employee Benefits
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:
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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.
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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.
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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.
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Financial Management: Achieve growth and profitability targets for the regional office. Drive initiatives to improve overall financial performance, including cross-selling.
Qualifications:
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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.
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:
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Full annual salary and bonus opportunities
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Most Benefits starting day one
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Medical, Dental, Vision Insurance
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Flex Spending or Health Savings Account
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401(k) with company match
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Profit-sharing/Defined contribution (1-year waiting period)
•
PTO/Paid Holidays
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Maternity Leave & Parental Leave
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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? Follow us on www.CottinghamButler.com | LinkedIn | Facebook
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