Regional Sales Leader - Employee Benefits
About the job
- Five or more years of proven sales leadership experience within the employee benefits insurance industry.
- A strong track record of achieving sales targets and driving business growth.
- Ability to develop and mentor a high-performing sales team.
- Ability to translate strategic vision into action.
- Strong relationship-building skills with clients, insurance carriers, and vendors.
- Lead regional employee benefits sales efforts by 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.
- Execute and implement the employee benefits vision and strategy for the regional office, translating it into actionable annual operational plans.
- Promote identification and evaluation of new products, services, and processes to enhance practice performance.
- Ensure the Employee Benefits service model exceeds client expectations and revenue retention targets.
- Review work products to meet service standards.
- Develop relationships with insurance carriers and partners to offer unique benefits and differentiate from competitors.
- Achieve growth and profitability targets for the regional office.
- Drive initiatives to improve overall financial performance, including cross-selling.
About the company
Cottingham & Butler is a large, privately held U.S. insurance broker focused on property & casualty and employee benefits. It helps clients manage risk by assessing needs, designing and placing insurance programs with carrier partners, and providing ongoing advisory, service, and claims support. Compared with competitors, it differentiates itself through its independence (not owned by carriers), scale, and a promise of consistent, improved outcomes—articulated as Better Every Day: better advice, better service, and better ideas than peers. The company emphasizes challenging conventional wisdom, innovating its services, and improving client results as it grew from 1887 to become the 3rd largest independently held broker. Its goal is to deliver measurable value for clients every day, helping them reduce risk and optimize benefits while maintaining strong growth and industry expertise.
Company Size
501-1,000
Company Stage
N/A
Total Funding
N/A
Headquarters
Dubuque, Iowa
Founded
1987
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Simplify's Take
What believers are saying
- The September 2026 Transportation Summit signals active demand generation and client intimacy.
- A 1,300-person national platform gives Hessling immediate distribution and cross-sell capacity.
- July 2026 leadership promotions suggest internal bench strength and continued growth investment.
What critics are saying
- The 2025 Massachusetts data incident keeps creating legal and reputational exposure.
- Transportation concentration ties results to trucking cycles, fleet claims severity, and carrier pricing.
- If Hessling fails to scale beyond trucking, niche dependence limits growth and valuation.
What makes Cottingham & Butler unique
- Mike Hessling became president on January 19, 2026, sharpening strategic execution.
- C&B runs one of the largest specialized trucking practices nationwide, per July 2026.
- The firm serves employers across property, benefits, captive, claims, and safety consulting.
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Benefits
- Health Insurance
- Dental Insurance
- Vision Insurance
- Health Savings Account/Flexible Spending Account
- 401(k) Company Match
- Profit Sharing
- Unlimited Paid Time Off
- Paid Holidays
- Company-paid ST and LT Disability
- Maternity Leave
- Parental Leave
- Subsidized Parking