Founding Medicare Consultant

The Pocket Protector; United States; Remote; USD 79,000 - 159,000; Full time

Job summary

The Pocket Protector is creating a new kind of Medicare agency focused on trust and clarity. As an entry-level consultant, you will guide clients through complex Medicare options, contributing to the agency's foundational processes and shaping future advisory practices. This full-time position offers competitive pay, a focus on customer service, and opportunities for growth within the company.

Benefits

Generous PTO and paid company holidays

Company-provided equipment stipend

Residual income from recurring business

Qualifications

• Passion for customer-first service and proven sales performance.
• Experience in a fast-changing environment with process building.
• Comfortable with video calls and new software.

Responsibilities

• Conduct individualized needs analyses for Medicare plans.
• Maintain accurate customer records in the CRM.
• Translate Medicare rules into clear choices for clients.

Skills

Customer service

Consultative sales

Tech-savvy

Education

Active health-insurance license or significant Medicare sales experience

Tools

HubSpot

Job description

Help build the Medicare agency we’ve always wished existed.

Why ThePocketProtector is different

AtThePocketProtector, we believe Medicare advice should feel like a conversation—not a sales pitch. We’re creating a new kind of Medicare agency that prioritizes trust, clarity, and personal guidance over pressure and quotas. As one of our very first consultants, you won’t just serve clients—you’ll help design the processes, playbooks, and culture that future advisors will follow.

The impact you’ll have

• Shape the blueprint.As a founding team member you’ll co‑create workflows, sales scripts, and service standards that will scale with us.
• Guide seniors with empathy.You’ll meet clients via inbound calls, Zoom, chat, and email—never cold calling—and translate complex Medicare rules into clear, actionable choices.
• Influence future talent.Your feedback will inform how we hire, train, and coach the next generation of consultants.

What you’ll do

• Conduct individualized needs analyses and recommend Medicare Advantage, Supplement, and PartD plans.
• Complete all enrollments accurately and compliantly.
• Maintain meticulous notes in our CRM (HubSpot experience is nice to have—we’ll train you).
• Stay current on Medicare regulations and carrier updates.
• Represent the company on camera—comfortable, professional Zoom presence is essential.
• Collaborate cross‑functionally to iterate on scripts, job aids, and performance metrics.
• Work extended or weekend hours during the Annual Enrollment Period (Oct15–Dec7); expect up to 50–55 hours per week then, with overtime pay. Outside AEP, a standard 40‑hour week is typical.

What you’ll bring

• Passion for customer‑first service and a track record of meeting or exceeding consultative sales goals.
• Ability to thrive in an early‑stage, fast‑changing environment—process building excites you.
• Active health‑insurance license**or** significant Medicare sales experience (we can assist with licensing for the right candidate).
• Tech‑savvy: adept with video calls; comfortable learning new software quickly.
• Bonus points for prior HubSpot or similar CRM usage.

What’s in it for you

• Residuals from Year1 for recurring book of business.
• Competitive hourly base + carrier‑agnostic bonuses.
• Omni-Channel client engagement - no prospecting, cold calling, or taking unqualified/uninterested "transfers".
• 100% remote; company‑provided equipment stipend.
• Generous PTO and paid company holidays (additional floating days after AEP).
• Opportunity to grow into team lead or training roles as we scale.

Secure, professional remote setup

A private, quiet workspace with limited access, screen‑privacy measures, and lockable storage for any PHI is required to protect customer data and meet HIPAA standards.

• Ready to set a new standard for Medicare guidance—and leave the traditional call‑center vibe behind? Apply here: thepocketprotector.com

Seniority level

• Seniority level

  Entry level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Consulting, Information Technology, and Sales

• Industries

  Insurance Agencies and Brokerages

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