Sales Leader - Wholesale Sales Manager

Job Title: Benefit Services Sales Manager

Reports To: Executive Vice President, Benefit Services

Position Summary: As our Benefit Services Sales Manager, you’ll lead a high‑performing team that sells an integrated solution—SISCO(medical TPA), HealthCheck360 (wellness & advocacy), medical management, and BCC (HRIS/consolidated billing). Your charter: grow a sales team, build broker relationships coast‑to‑coast, win complex business and scale a connected platform that lowers claims cost, boosts engagement, and simplifies administration. You’ll hire, coach, and elevate sales executives, set strategy, and partner with executive leadership on product and marketing to accelerate new business and retention.

Essential Functions:

• Supervise all sales executives, including setting activity metrics, holding regular sales meetings, and ensuring that the sales 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/events, and web-generated opportunities.


• Formulate strategies to increase penetration and engagement with top brokers in the US.


• 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; ensure all sales executives understand and can articulate these differences.


• Complete other duties as assigned by the Executive Vice President.

Metrics of Success:

• New business generated each year


• Business retention rates


• Number of successful sales executives


• Significant penetration of new brokers

Education: Four-year degree.

Experience: Minimum of 5 years of sales management experience, preferably within the employee benefits industry.

Specific Skills & Knowledge:

• Strong leadership skills with the ability to hold others accountable.


• Excellent sales management skills and practices.


• Ability to hire and develop sales talent.


• Solid understanding of the employee benefits business.


• Knowledge of the wellness business and its applicability for companies.


• Basic knowledge of CRM systems; proficiency in Hubspot and/or Salesforce is a plus.


• Obtaining and maintaining a Life and Health Insurance License is recommended but not required.

Supervisory Responsibility: This individual will manage the sales team, which includes 10+ sales executives.

About HealthCheck360:

At HealthCheck360, we turn our passion into your program. We’re leaders in population health management and well-being solutions. Our services are like a choose your own adventure book. Select the options you need to fill gaps in your current benefits or create a comprehensive program to fit your organization’s unique culture. We can even work with your brokers, third party administrator, insurance companies or other benefit provider for a complete integration of services.

The HealthCheck360 difference is our focus on you. Our approach includes developing a well-being strategy to address individual and population health and get you the data you need to take action. When your employees are healthy, we all win.

Want to learn more? Follow us on www.CottinghamButler.com | LinkedIn | Facebook