Strategic Benefit Services Sales Leader

HealthCheck360; Dubuque (IA); On-site; USD 90,000 - 130,000; Full time

Benefits offered by this job

Medical, Dental, Vision Insurance

401(k) with company match

PTO/Paid Holidays

Maternity Leave & Parental Leave

Flex Spending or Health Savings A/C

Job summary

HealthCheck360 seeks a Benefit Services Sales Manager to lead a high‑performing sales team selling SISCO, wellness, medical management, and HRIS/consolidated billing solutions. The role focuses on growing the broker network coast‑to‑coast, winning complex business, and scaling a connected platform to lower costs and boost engagement.

You will hire, coach, and elevate sales executives, set strategy, and align with product and marketing leadership to accelerate new business and retention.

Qualifications

• Five+ years of experience in employee benefits or related field.
• Experience leading a sales team and managing brokers or partners.
• Strong understanding of benefits programs and wellness services.
• Proven ability to hire, coach, and scale a sales force.

Responsibilities

• Supervise all sales executives and set activity metrics.
• Accompany executives on calls to close business.
• Train and develop new sales staff; implement development plans.
• Define sales territories to maximize coverage and minimize overlap.
• Develop policies for handling incoming leads from national portals and events.
• Formulate strategies to increase broker penetration and engagement.
• Partner with leadership on product pricing and marketing priorities.
• Become an expert on HealthCheck360 and SISCO products and differentiation.

Skills

Leadership

Sales management

Talent development

Employee benefits knowledge

Wellness industry knowledge

CRM proficiency

Life and Health Insurance knowledge (L

Education

Bachelor's degree

Tools

HubSpot

Salesforce

Job description

HealthCheck360 seeks a Benefit Services Sales Manager to lead a high‑performing sales team selling SISCO, wellness, medical management, and HRIS/consolidated billing solutions. The role focuses on growing the broker network coast‑to‑coast, winning complex business, and scaling a connected platform to lower costs and boost engagement.

You will hire, coach, and elevate sales executives, set strategy, and align with product and marketing leadership to accelerate new business and retention.