Sales Leader - Benefits Wholesale Services
- Location
- Dubuque, IA · On-site
- Job type
- Full-time
- Level
- Lead / Staff
- Experience
- 5+ years
- Education
- Bachelor's degree
- Listed
- 31 days ago
Skills & highlights for this role
- sales team management
- employee benefits industry knowledge
- broker relationship development
Also useful
- wellness programs
- HubSpot
- Salesforce
Stated benefits & perks
- Medical
- Dental
- Vision
- 401k match
- Parental leave
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!
From HealthCheck360's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
Rolev.ai is a job search and application tool for US job seekers. For this Sales Leader - Benefits Wholesale Services role at HealthCheck360, it shows how your resume fits, tailors your resume to the posting, and prepares the application for you to review.
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Common questions
Where is the Sales Leader - Benefits Wholesale Services job at HealthCheck360 located?
This Sales Leader - Benefits Wholesale Services position at HealthCheck360 is located in Dubuque, IA (On-site). Always check HealthCheck360's application page for specific state eligibility or relocation policies.
What qualifications are required for Sales Leader - Benefits Wholesale Services at HealthCheck360?
For the Sales Leader - Benefits Wholesale Services role, HealthCheck360 highlights 5+ years of relevant experience; a bachelor's degree; experience with sales team management, employee benefits industry knowledge, broker relationship development. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.
How do I apply for the Sales Leader - Benefits Wholesale Services position at HealthCheck360?
This listing links directly to HealthCheck360's Greenhouse application page. You can apply directly on HealthCheck360's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Greenhouse application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.