Medicare Insurance Field Agent
In-Store Enrollment Specialist — National Retailer Kiosk Program
AEP 2026 | Oct 15 – Dec 7 | Performance-Based Compensation | Path to Year-Round
Base Pay Per-App Bonus
$18/hr guaranteed
Per-App Bonus
$175 per enrollment
Schedule
32 hrs/wk · 32 hrs/wk
Season Length
54 days · Oct 15–Dec 7
About the Role
We are looking for high-energy, people-first sales professionals to join our Medicare enrollment program inside major retailer stores. This is not a desk job and it is not cold calling. You will be stationed at a branded kiosk inside one of the busiest retail environments in the country, meeting seniors where they already shop, having real conversations, and helping them find Medicare Advantage plans that fit their lives.
Think of the best field rep you have ever seen at a home improvement expo, a pest control table outside a hardware store, or a wireless carrier kiosk in a mall. That is the energy this role demands — approachable, confident, consultative, and relentless about hitting a number. If you have ever thrived in a high-contact, performance-driven sales environment, this role was designed for you.
This position runs through the Annual Enrollment Period (AEP) — the single most important selling window in Medicare. Top performers will be offered continued roles through the Open Enrollment Period (OEP) in January and beyond, with the path to a year-round position for those who prove themselves.
What You Will Do
- Engage seniors and Medicare-eligible shoppers on the retailer floor — start conversations, qualify interest, and guide enrollments from introduction to application
- Educate consumers on Medicare Advantage plan options, benefits, and how to compare coverage — no prior insurance experience required, we train you
- Complete enrollment applications on a tablet using carrier-approved software, ensuring 100% accuracy and CMS compliance on every submission
- Meet and exceed daily and weekly enrollment targets set by your field manager
- Track your own performance, report daily app counts, and participate in weekly team calls
- Maintain a clean, professional kiosk presence and represent the program with integrity at all times
- Follow all retailer conduct guidelines and CMS marketing compliance rules — these are non-negotiable
- Provide every consumer with required TPMO (Third Party Marketing Organization) disclosures before discussing any plan details
Keys to Success
This role operates under strict CMS marketing guidelines. You cannot approach shoppers unsolicited or station yourself outside your designated kiosk area. What this means in practice is that your enrollment volume will be almost entirely driven by two things: referrals from store staff and people who walk up to your kiosk on their own. That changes what this job requires at its core.
Your single most important non-enrollment activity is relationship building inside the store. The store manager, assistant managers, pharmacy staff, vision center team, and department associates all interact with Medicare-eligible customers every single day. An agent who earns their trust and stays top of mind will have a steady flow of warm referrals. An agent who sits quietly at a kiosk waiting for people to wander over will struggle. The best performers in this program treat the store like their territory and the employees like their partners.
Building your referral network inside the store
- Pharmacy staff — your highest-value internal referral source. Pharmacists and pharmacy techs interact directly with Medicare patients filling prescriptions every day. Build a genuine relationship, explain what you do, and make it easy for them to point someone your way when they hear “I’m trying to figure out my Medicare coverage.”
- Vision center staff — many Medicare Advantage plans include vision benefits. Vision center opticians and associates are natural allies. A customer asking about eyeglass coverage under Medicare is a warm referral waiting to happen.
- Store manager and assistant managers — introduce yourself early, be professional, and keep them informed about what you do. A store manager who understands your program and believes in it becomes an internal advocate. One who does not know who you are is a risk to your kiosk placement.
- Department associates and cashiers — associates in health and wellness, electronics, and customer service interact with seniors constantly. A simple “if anyone asks about Medicare, send them my way” conversation, done genuinely and repeatedly, adds up.
- Store employees, their families, and their networks — do not overlook the people you work alongside every day. The retailer employs a lot of people, many of whom have parents, grandparents, or spouses on Medicare or approaching Medicare age. A pharmacy tech who trusts you might mention you to her mother. A store manager who sees you helping customers might refer his father-in-law. The relationships you build inside the store are not just a referral pipeline — they are a client pipeline. Treat every employee like a potential customer and every customer like a potential referral.
What this means for your kiosk presence
Your kiosk should be the most welcoming, approachable spot in the store. Clear signage, a clean setup, and an agent who looks engaged and happy to talk. When someone makes eye contact or slows down near the booth, that is your moment. When a pharmacy tech sends someone your way, that person already knows why they are walking over. The agents who figure out how to manufacture those moments consistently — through relationships, through kiosk positioning, through energy — are the ones who hit Platinum. And because every enrollment counts toward your goals — whether it comes from the store floor, a phone call, a friend, a neighbor, or a family referral — your opportunity is not limited to the people who walk past your kiosk. Think of the kiosk as your base, not your ceiling.
Important: You’ll work within designated kiosk guidelines — staying in your area and letting conversations come to you through referrals and walk-ups. It’s a straightforward framework once you get the hang of it, and the agents who embrace it almost always outperform those who don’t. Build the right relationships in the store and you won’t need to do anything else.
Who We Are Looking ForYou are a natural on your feet
You do not wait for people to come to you. You initiate. You are comfortable walking up to a stranger, reading the room in two seconds, and opening a conversation that does not feel like a pitch. You know how to be warm without being pushy and direct without being aggressive.
You have a track record in field or retail sales
We are not looking for insurance veterans — we are looking for sales athletes. If you have sold door-to-door, worked a retail kiosk, run a trade show booth, knocked on doors for solar or roofing, or worked lead-gen for any home services company, you already have the instincts this role requires. The insurance knowledge we will teach you.
You are motivated by performance pay
The base hourly is your floor, not your goal. The people who thrive here are the ones who see a $175 per-app bonus and start calculating how many conversations they need to have per shift. You are energized by a number on the board and you know how to push through slow hours to find your next enrollment.
You are coachable
The best agents in this program are open to feedback and willing to adjust. You will receive coaching from your field manager, participate in weekly calls, and be expected to incorporate what you learn quickly. If you can take direction, stay coachable, and keep improving through a fast-moving 54-day season, you will do very well here.
Compensation & Earnings
Base Hourly Rate
$18/hr guaranteed while on shift
Per-Enrollment Bonus
$175 for every completed Medicare Advantage application
Bronze Milestone
$2,500 bonus — reach 50 enrollments for the season
Silver Milestone
$5,000 bonus — reach 100 enrollments for the season
Gold Milestone
$7,500 bonus — reach 150 enrollments for the season
Platinum Milestone
$10,000 bonus — reach 200 enrollments for the season
In-Season Contests
Weekly cash prizes, gift cards, and leaderboard rewards announced each AEP
OEP Continuation
Top performers invited back for Open Enrollment (Jan–Mar) — same comp structure
What can you earn?
Season Total Apps
Base Pay
App Bonuses
Total Earnings
50 apps (Bronze)
$2,540
$8,750 + $2,500 milestone
$13,790
100 apps (Silver)
$2,540
$17,500 + $5,000 milestone
$25,040
150 apps (Gold)
$2,540
$26,250 + $7,500 milestone
$36,290
200 apps (Platinum)
$2,540
$35,000 + $10,000 milestone
$47,540
Note: Milestone bonuses are one-time payouts at whichever tier you finish the season. Base pay calculated at 32 hrs/wk x 7.71 weeks x $18/hr. Actual earnings vary by production.
Schedule & Location
- Season runs October 15 through December 7, 2025 (54 days — the Annual Enrollment Period)
- 32 hours per week — schedule set by your field manager based on store traffic and business needs
- 6 to 8 hour shifts — daytime hours, no nights
- You will be assigned to a specific retailer location near your home
- Your primary base is your assigned retailer kiosk — but every enrollment you write counts toward your goals, regardless of where it originates. Friends, family, neighbors, phone referrals, outside appointments — it all adds up and it all counts
- Top performers may be asked to cover additional stores or shifts during peak weeks
RequirementsRequired
- State health insurance license required
- Must pass AHIP (America's Health Insurance Plans) certification — required annually for all Medicare agents, approximately 4 to 8 hours online, cost covered by the program
- Must pass carrier-specific certifications for each plan we sell — completed online before the season starts
- Must pass a background check — required for both insurance licensing and Walmart in-store access
- Must be comfortable standing and engaging on a retail floor for full shift duration
- Must have reliable transportation to your assigned location
Strongly Preferred
- 1+ years of field sales, direct sales, retail sales, or lead-generation experience
- Experience in any of the following: home improvement sales, pest control, solar, roofing, wireless, financial products, medical devices, or any door-to-door / event sales role
- Bilingual (English/Spanish) strongly preferred in select markets — additional compensation available
- Prior Medicare, health insurance, or benefits experience — helpful but absolutely not required
What We Provide
- Full paid training — AHIP certification costs covered, carrier training completed before your first day
- Branded kiosk setup, approved marketing materials, and enrollment technology at your location
- A dedicated Field Manager who oversees your territory and is available for coaching and support
- Weekly team calls, performance coaching, and real-time leaderboard access
- Clear daily and weekly targets so you always know exactly where you stand
- Path to continued employment through OEP (January through March) and beyond for top performers
The Path to Platinum
At 200 enrollments for the season you earn Platinum status — $35,000 in per-app bonuses plus a $10,000 milestone check, on top of your base wages. That is $49.446 for 247 hours of work — the earning power of a $110,000 annual salary compressed into one enrollment season.
Platinum agents are first in line for OEP continuation, year-round roles, field manager consideration, and priority placement in premium store locations for next AEP.
Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. This role may be eligible for the following:
- Medical, dental & vision
- 401(k)/Roth
- Insurance (Basic/Supplemental Life & AD&D)
- Short and long-term disability
- Health & Dependent Care Spending Accounts (HSA & DCFSA)
- Transportation benefits
- Employee Assistance Program
- Time Off/Leave (PTO, Vacation or Sick Leave)
San Fran Candidates only: Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.
Los Angeles Candidates only: We will consider for employment all qualified applicants, including those with criminal histories, in a manner consistent with the requirements of applicable state and local laws, including the City of Los Angeles' Fair Chance Initiative for Hiring Ordinance.
Unincorporated Los Angeles County Candidates Only: Qualified applicants with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act. Where applicable, in accordance with the Los Angeles County Fair Chance Ordinance for Employers, Candidates must satisfy all pre-employment screening criteria and may be disqualified due to criminal history because the requirements of this position, as outlined above, may include: access to valuable company assets; exercise of good judgment and performance of duties safely under work conditions that may be stressful including under supervision of client; access to sensitive personal or financial information; and/or access to objects that may be used to inflict injury or harm to others.
Pay: $18.00 - $35.00 per hour
Work Location: In person
