Benefit Services Sales Manager - Wholesale Sales Manager
About the job
- A four-year degree is required.
- At least 5 years of sales management experience is required; experience in the employee benefits industry is preferred.
- Strong leadership skills and the ability to hold others accountable are required.
- Strong sales management skills and practices are required.
- The ability to hire and develop sales talent is required.
- A solid understanding of the employee benefits business is required.
- Knowledge of the wellness business and its applicability for companies is required.
- Basic knowledge of customer relationship management systems is required.
- Obtaining and maintaining a Life and Health Insurance License is recommended but not required.
- Supervise all sales executives by setting activity metrics, holding regular sales meetings, and ensuring the team has the necessary resources to succeed.
- Accompany sales executives on calls as necessary to close business.
- Hire, train, and develop new sales executives; implement formal development plans and ensure comprehensive training.
- Define sales territories to avoid overlap and inefficiency.
- Develop policies and procedures for handling incoming leads from national portals, conferences and events, and web-generated opportunities.
- Formulate strategies to increase penetration and engagement with top brokers in the United States.
- Provide feedback to the Executive Vice President on product and pricing requirements to remain competitive.
- Collaborate with the Executive Vice President on marketing budget, priorities, and conference attendance; suggest new target verticals and distribution channels.
- Become an expert in the company’s products and differentiation, and ensure all sales executives understand and can articulate these differences.
- Complete other duties as assigned by the Executive Vice President.
- Proficiency in HubSpot and/or Salesforce is a plus.
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