Sales Leader - Benefits Wholesale Services

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

Job Title:

Benefit Services Sales Manager

Reports To:

Practice Leader, SISCO

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.
• 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 Practice Leader on product and pricing requirements to remain competitive.
• Collaborate with the Practice Leader 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 Practice Leader

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 experience in the employee benefits industry, preferably within the TPA and self-funding space.

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.

Pay & Benefits

• Full annual salary and bonus opportunities
• Most Benefits starting day one
  • Medical, Dental, Vision Insurance
  • Flex Spending or Health Savings Account
  • 401(k) with company match
  • Profit-sharing/Defined contribution (1-year waiting period)
  • PTO/Paid Holidays
  • Maternity Leave & Parental Leave
  • and so much more!