Employment Type:

Full‑Time, W‑2

Compensation:

$35/hour + Bonus

Benefits:

Full benefits package, unlimited PTO, paid holidays, paid leave, stock option eligibility

About Insuranceease

Insuranceease is a modern, tech‑forward insurance organization dedicated exclusively to serving the Medicare population. We combine industry‑leading compliance standards, advanced technology, and a people‑first culture to deliver clarity and confidence to seniors navigating their Medicare options. Our mission is to elevate the consumer experience while empowering licensed agents and leaders with the tools, training, and support they need to build long‑term, high‑performing careers.

Position Overview

We are seeking a detail‑oriented, process‑driven Learning & Development Specialist to support the training, onboarding, and ongoing development of our Leadership team and Sales Agents. This role plays a critical part in ensuring agents are fully prepared to operate compliantly, confidently, and effectively within a highly regulated environment.

The L&D Specialist will collaborate closely with leadership, compliance, and sales management to deliver training programs, maintain curriculum, track completion metrics, and ensure agents meet all regulatory and organizational requirements. This role is ideal for someone who thrives in a structured environment, enjoys teaching and coaching, and is passionate about building high‑performing teams.

Key Responsibilities

• • Support the development, delivery, and maintenance of training programs for Medicare Sales Agents, including onboarding, product training, compliance modules, and skill‑based development.
  • Facilitate live and virtual training sessions that prepare agents for production, compliance expectations, and performance standards.
  • Track, monitor, and report on training completion, certification status, and ongoing L&D requirements for all team members.
  • Collaborate with Sales Managers to ensure agents complete required training and demonstrate competency in key areas.
  • Maintain and update training materials, SOPs, job aids, and knowledge‑base content to reflect regulatory changes and operational updates.
  • Partner with compliance teams to ensure all training content aligns with CMS regulations and internal quality standards.
  • Provide one‑on‑one coaching or refresher training for agents who need additional support.
  • Assist in evaluating agent performance trends to identify training gaps and recommend targeted development initiatives.
  • Support the rollout of new systems, tools, and processes by creating training content and facilitating adoption.

Compensation

• • $35/hour (W‑2)
  • Annual Bonus: tied to training outcomes, agent readiness metrics, and departmental performance

Benefits

• • Full medical, dental, and vision benefits
  • Unlimited PTO
  • Paid holidays and paid leave
  • Eligibility for company stock options (details provided in offer letter)
  • Career advancement opportunities within training, compliance, and leadership

Qualifications

• • Experience in Medicare insurance, health insurance, or a regulated sales environment preferred
  • Prior experience in training, coaching, instructional design, or L&D support roles
  • Strong understanding of compliance, quality assurance, and Medicare regulatory requirements (or willingness to learn quickly)
  • Excellent communication and presentation skills, both in live and virtual settings
  • Highly organized with strong attention to detail and documentation accuracy
  • Comfortable using LMS platforms, CRM systems, and digital training tools
  • Ability to collaborate cross‑functionally with sales, compliance, and leadership teams

Who Thrives Here

We’re looking for someone who is:

• • Patient, supportive, and passionate about developing others
  • Highly organized and process‑driven
  • Strong in communication and instructional delivery
  • Comfortable in a fast‑paced, metrics‑driven environment
  • Motivated by improving agent performance and compliance outcomes