Sales Trainer

Top Talent. Right Plan. Healthier You

Are you an entrepreneur at heart? Do you thrive on building your own success, taking ownership of your work, and making a real impact? At Wise Choice, we're looking for visionary self-starters to join our remote-first team—where you're in control of your growth, your income, and your future.

At Wise Choice, our mission is to expertly guide consumers through their health insurance and related options when, where, and how they prefer. We're creating a better way – one that's transparent and trustworthy for both our consumers externally and our employees internally.

We're seeking an experienced and energetic Sales Trainer to lead product education and sales skill development for new and tenured agents. This role is critical to our growth strategy and will play a hands-on role in building a scalable, high-performing sales training program from the ground up.

This position is fully remote

Quick Facts About Wise Choice Senior Solutions

• Founded:
  April 2024
• Mission:
  Redefining Medicare by putting people first (Talent & Senior), one Wise Choice at a time.
• Vision:
  Earn More. Work Less. No Micromanagement.
• Traction: One of the fastest-growing insure-tech start-up teams.
• Key investors: Innovative Financial Group (IFG), FYM Financial, Humana
• Team size: 45+ agents & full-time equivalents (April 2025) and targeting 300+ by end of 2026
• 
  
  Location:
  
  100% remote (US required, preferably Midwest/Eastern Time Zone)

What you'll do:

• Design and deliver engaging onboarding programs for Medicare and Final Expense sales agents (licensed and pre-licensed)
• Develop training content for products, sales scripts, objection handling, compliance, and CRM/enrollment tools
• Facilitate live virtual and/or in-person training sessions on sales techniques, industry updates, and carrier guidelines
• Support agents through licensing preparation, AHIP training, and carrier certifications
• Partner with Sales Leadership to assess training effectiveness and track agent performance metrics
• Create and maintain a centralized knowledge base and learning library
• Provide one-on-one coaching and skill refreshers to underperforming or new agents
• Stay current on CMS guidelines, state insurance regulations, and carrier updates
• Collaborate cross-functionally with Marketing, Compliance, and Tech teams to ensure alignment across the agent experience

Who are you:

• 3+ years of experience training licensed Medicare and/or Final Expense agents
• Strong understanding of Medicare Advantage, Medicare Supplement, and life insurance products
• Proven ability to teach complex topics in a clear, engaging, and compliant manner
• Experience with remote learning tools, LMS platforms, and CRM/enrollment systems
• Passion for coaching, mentoring, and developing others
• Excellent communication and facilitation skills
• Life & Health Insurance License required
• AHIP certification preferred

Why Wise Choice?

• Join an organization that values boldness, ambition, collaboration, and a customer-centric approach
• Work in a dynamic, entrepreneurial environment with a strong team spirit
• Career advancement opportunities in a high-growth startup
• Enjoy competitive compensation + performance bonus

About Us:

Wise Choice was founded in 2024, and we're more than just a company—we're a team dedicated to simplifying Medicare for seniors nationwide. Built by Agents for Agents. With a focus on integrity, innovation, and exceptional service, we empower our agents to succeed while making a real impact. Join us and be part of a supportive culture that puts you first. Ready to Get Started?

If you're driven to succeed and passionate about helping others, we want to hear from you!