Sales Representative Target Area:
Position 1: Nebraska & Iowa
Position 2: Kansas & Missouri
Company Overview
WellGuard Assurance is a Tennessee health captive insurance organization within the VerraCare healthcare eco-system. WellGuard Assurance connects small businesses with comprehensive, affordable group health coverage and partners with employers across the United States to design benefit solutions that protect their teams and support business growth.
At WellGuard Assurance, people are a greatest asset, beginning with the advisors who represent the organization in the field and help brokers, consultants, employers, and small business leaders understand coverage options.
Position Summary
WellGuard Assurance is seeking a motivated and experienced Small Group Health Insurance Sales Representative to join the growing sales team. In this field-based role, the representative will prospect, develop, and close new group health insurance accounts with small businesses typically employing between 3 and 100 employees.
The role serves as a trusted advisor to independent brokers, agents, and HR consultants by guiding them through plan options and helping build benefit packages that meet the needs of their small group customers.
This is an opportunity for a driven sales professional who is passionate about health insurance and wants to make a meaningful impact in the small business community.
Essential Duties and Responsibilities
Sales Prospecting & Pipeline Development
· Prospect and develop a pipeline of small group employer accounts through cold outreach, referrals, broker partnerships, networking events, and community engagement.
· Identify and qualify opportunities within the assigned territory and maintain disciplined sales activity to support monthly and quarterly production goals.
· Track all sales activity, pipeline status, account details, and follow-up items accurately within the company CRM system.
Broker, Employer & Consultant Engagement
· Conduct in-person meetings and presentations with brokers, HR administrators, and key decision-makers to assess employee benefits needs.
· Serve as a trusted advisor to independent brokers, agents, and HR consultants by helping them evaluate benefit solutions for small group customers.
· Build and maintain strong relationships with local broker networks, chambers of commerce, small business associations, and community partners.
Plan Presentation, Quoting & Enrollment Support
· Present and recommend appropriate group health insurance plans, including medical, dental, vision, and ancillary products where applicable.
· Prepare accurate and competitive group quotes in coordination with internal underwriting and carrier partners.
· Guide clients and broker partners through the enrollment process to support a smooth and compliant onboarding experience.
Account Management, Retention & Growth
· Manage and grow a book of business by maintaining strong broker and client relationships, conducting annual renewal reviews, and identifying upsell or cross-sell opportunities.
· Collaborate with internal service and support teams to resolve client issues and support high levels of client satisfaction and retention.
· Meet or exceed monthly and quarterly sales targets and production goals established by sales leadership.
Compliance & Market Knowledge
· Stay current on state and federal regulations affecting small group health insurance, including ACA compliance requirements.
· Maintain strong knowledge of group health insurance products, plan design, carrier markets, and small employer group coverage options.
· Represent WellGuard Assurance professionally and ethically in the marketplace and escalate compliance or operational concerns appropriately.
Qualifications
Education & Experience
· 3 to 5 years of demonstrated experience in group health insurance sales, employee benefits sales, or a related field-based business development role.
· Active state health insurance license (Life and Health), or ability to obtain required licensure within 90 days of hire.
· Proven track record of meeting or exceeding sales quotas in a field-based, territory-based, or business development role.
· Experience working specifically with brokers in the 2-to-100 employee market segment preferred.
Technical & Professional Skills
· Strong knowledge of group health insurance products, plan design, and carrier markets serving small employer groups.
· Excellent communication, presentation, negotiation, and consultative selling skills with the ability to build rapport with business owners and decision-makers.
· Proficiency with CRM software and standard productivity tools, including Microsoft Office or equivalent platforms.
· Familiarity with ACA small group market rules and level-funded or self-funded plan alternatives preferred.
· Industry designations such as REBC or CEBS are a plus.
Territory & Relationship Management
· Self-motivated and highly organized, with the ability to manage a territory independently and prioritize a high-volume pipeline.
· Established relationships with local broker networks, chambers of commerce, or small business associations preferred.
· Ability to travel locally and regionally for field meetings, networking events, broker presentations, and community engagement.
Key Competencies
Sales Acumen
Builds and advances a disciplined, qualified pipeline.
Prospects consistently, qualifies opportunities, maintains follow-up, and converts new business within assigned production goals.
Consultative Benefits Advising
Connects small group needs with appropriate coverage options.
Assesses employer and broker priorities, explains plan options clearly, and recommends benefit solutions aligned with customer needs.
Broker Relationship Management
Develops trusted relationships with brokers, agents, referral partners, and small business networks.
Maintains proactive contact, supports renewal conversations, and serves as a responsive WellGuard Assurance partner.
Communication & Presentation
Explains complex insurance concepts in a clear, professional manner.
Delivers effective presentations to brokers, HR administrators, business owners, and decision-makers.
Negotiation & Influence
Positions value and navigates objections while preserving credibility.
Addresses questions, reinforces differentiators, and guides decisions through preparation and sound business judgment.
Compliance Judgment
Applies regulatory awareness and ethical sales practices.
Maintains awareness of ACA and state requirements, supports compliant enrollment, and escalates questions appropriately.
Results Orientation
Takes ownership of activity, outcomes, and follow-through.
Meets monthly and quarterly sales goals, keeps CRM records current, and follows through on client and broker commitments.
Territory Management
Plans and prioritizes work independently across a regional territory.
Balances prospecting, meetings, renewals, networking, account support, and travel requirements effectively.
Working Conditions and Physical Requirements
· Field-based sales role requiring regular local and regional travel for broker meetings, employer presentations, networking events, and community engagement.
· Requires use of standard office equipment, CRM systems, productivity tools, and virtual meeting technology.
· May require extended hours or occasional non-standard business hours to support client meetings, renewal cycles, enrollment activity, or sales events.
· Mileage reimbursement and business expense support are available for eligible field activities.
Compensation & Benefits
· Base salary plus an uncapped commission structure tied to new business production.
· Comprehensive health, dental, and vision insurance benefits for eligible employees and dependents.
· Paid time off, including vacation, sick leave, and company-observed holidays.
· Ongoing professional development, carrier training, and support for licensure and industry certifications.
· Collaborative team environment with leadership support and a clear path for career advancement.
Pay: From $110,000.00 per year
Benefits:
- 401(k) matching
- Dental insurance
- Disability insurance
- Health insurance
- Paid time off
- Vision insurance
- Work from home
Work Location: Remote
