Seasonal Agent Support Representative Jobs (NOW HIRING)

About Us

Health and Medicare Agency, which is a full-service insurance brokerage focused on helping agents build independent, long-term businesses. We are a hands-on, growth-focused organization that values accountability, ownership, and results. Our agents rely on us not just for products but for structure, support, and strategy.

As we continue to grow, we are looking for someone who can help us scale without compromising the culture and high standards that set us apart.

Position Overview

This is not a typical administrative role.

We are seeking a high-ownership Operations & Agent Support Manager who can keep the business running smoothly, stay ahead of what’s coming next, and step in to support both the team and our agents when needed.

This role requires someone who naturally anticipates needs, takes initiative, and operates with a strong sense of ownership. You will be responsible for keeping projects on track, ensuring key reporting is handled proactively, and supporting agents—especially during high-volume seasons such as AEP and OEP.

Some days you will be managing priorities and ensuring accountability. Other days, you will step directly into execution—assisting with commissions, supporting agents on calls, or helping move critical work forward.

If you are someone who says, “I already took care of that,” this role is for you.

Key Responsibilities

1. Forward Planning & Operational Control

• Maintain and track key production metrics, including monthly award and recognition tracking
• Ensure accurate, up-to-date reporting so leadership is never behind or reacting last-minute
• Anticipate upcoming needs (AEP, OEP, events, recruiting cycles) and prepare accordingly
• Ensure the right agents are identified, recognized, and included in company initiatives
• Keep leadership informed with clear visibility into priorities, timelines, and progress

2. Agent Support (AEP/OEP & Ongoing)

• Assist agents with overflow calls and basic service-related needs
• Provide professional, responsive support to agents and clients
• Serve as a reliable point of contact during high-volume periods
• Represent NBP with professionalism, confidence, and accuracy

3. Execution & Operational Support

• Assist with commission processing and reconciliation during peak periods (Jan–Mar)
• Support recruiting coordination, including tracking candidates and scheduling
• Step in to complete high-priority work when workload exceeds team capacity
• Ensure all work is completed with a high level of accuracy and attention to detail

4. Team Coordination & Accountability

• Track active projects and ensure deadlines are met
• Follow up with team members to maintain accountability
• Identify bottlenecks and take initiative to resolve them

What We’re Looking For

Required Traits

• Highly organized with strong attention to detail
• Strong sense of ownership and follow-through
• Naturally proactive—anticipates needs rather than waiting for direction
• Comfortable managing multiple priorities in a fast-paced environment
• Confident communicator who can interact professionally with agents and team members
• Willingness to step in wherever needed to ensure results

Preferred Experience

• Operations, office management, or project coordination experience
• Experience in insurance, financial services, or a service-based industry (preferred but not required)
• Familiarity with CRM systems or tracking tools

What Makes Someone Successful in This Role

• You are already working on the next task before being asked
• You take pride in staying ahead and keeping others organized
• You do not wait for direction—you take initiative
• You are comfortable stepping in to help during busy seasons
• You represent the company with professionalism and confidence

We previously had someone in this role for many years who consistently stayed one step ahead. That is the standard we are looking to maintain.

What Success Looks Like (First 90 Days)

• Monthly tracking and reporting is accurate and up-to-date
• Projects move forward without constant oversight
• Leadership has clear visibility into priorities and progress
• Agents receive timely, professional support—especially during busy periods
• The organization is operating proactively, not reactively

Compensation

• Competitive salary based on experience ($45,000–$65,000)
• Performance-based bonus opportunities
• Opportunity for long-term growth within the organization

How to Apply

We are looking for someone who takes ownership, stays ahead, and follows through.

Please submit your resume along with a brief note answering this question:

“Tell us about a time you anticipated a problem or need before it happened and what you did to address it.”

We are an equal opportunity employer.