Strategic Benefit Services Sales Leader

Cottingham & Butler; Dubuque (IA); On-site; USD 110,000 - 170,000; Full time

Job summary

HealthCheck360 is seeking a Benefit Services Sales Manager to lead a high‑performing team selling an integrated platform including SISCO, HealthCheck360, medical management, and HRIS/consolidated billing. You will grow the sales organization, nurture broker relationships coast‑to‑coast, and drive new business and retention.

You will hire, coach, and elevate sales executives, define strategy, and partner with executive leadership on product and marketing to accelerate growth.

Qualifications

• Minimum 5 years of sales management experience, preferably in the employee benefits industry.
• Strong leadership and coaching capabilities.
• Deep understanding of employee benefits offerings and market dynamics.
• Proficiency with CRM systems (HubSpot/Salesforce a plus).

Responsibilities

• Supervise all sales executives, set activity metrics and lead regular sales meetings.
• Accompany sales executives on calls to close business.
• Hire, train, and develop new sales executives with formal development plans.
• Define sales territories to prevent overlap and boost efficiency.
• Create policies for handling leads from portals, conferences, and web inquiries.
• Develop strategies to penetrate top brokers across the US.
• Provide product and pricing feedback to stay competitive.
• Collaborate on marketing budgets, priorities, and channels; master product differentiation.
• Handle other duties as assigned by the Executive Vice President.

Skills

Leadership

Sales management

Talent development

Employee benefits

CRM knowledge

Tools

HubSpot

Salesforce

Job description

HealthCheck360 is seeking a Benefit Services Sales Manager to lead a high‑performing team selling an integrated platform including SISCO, HealthCheck360, medical management, and HRIS/consolidated billing. You will grow the sales organization, nurture broker relationships coast‑to‑coast, and drive new business and retention.

You will hire, coach, and elevate sales executives, define strategy, and partner with executive leadership on product and marketing to accelerate growth.