Enrollment Specialist

Come work with MyHealthily!

Experienced Group Health Insurance Sales – Enrollment Specialist

A little About MyHealthily

At MyHealthily we are obsessed. Obsessed with genuine Customer Service. Obsessed with solution focused thinking. Obsessed with driving positive change, and more importantly, producing mind boggling results.

This obsession starts at the beginning with our propriety platform that takes the frustration out of group health insurance. Small business owners, employees and the Brokers that serve them are stuck in an un-evolving loop. It’s no secret that small group health insurance isn’t the most advanced industry. We are working to fix that.

Who We’re Looking For

At MyHealthily we look for people who bring their whole genuine self-daily. You are self-motivated. You think like an entrepreneur. You crave being part of something different. You are detail oriented.

We are looking for that person that can lead a team of people whose objective is to provide that WOW customer service, whether it’s for direct business or assisting our partner Agency’s utilizing our proprietary software.

Company Culture Is Our Heart

  • We strive to deliver WOW customer service
  • Be creative, adventurous and open-minded
  • Bring passion and determination
  • Embrace and drive change
  • Pursue growth and learning

What we offer

  • Competitive salary
  • Remote work location of your choosing
  • Health benefits
  • Generous PTO
  • Stock Options
  • Fun and witty co-workers!


  • Act as player and coach as you support sales and business development for internal and partner Agents
  • Actively manage, lead, and perform hands on tasks to ensure accounts are successfully enrolled with insurance carriers
  • Interpret small group enrollment requirements across multiple carriers and multiple states to ensure accuracy of enrollments
  • Maintain an understanding of the product helping the team and customers maximize the use of the platform
  • Identify and play a leadership role in identifying gaps and improving department/company processes
  • Ensure customer inquiries are quickly and accurately satisfied with WOW satisfaction
  • Maintain documentation on workflows, procedures, and protocols
  • Maintain awareness on current and evolving health insurance industry standards and best practices


  • 10 years experience in services and enrollments, preferably in health and medical insurance
  • Health insurance license
  • Healthcare and Medical Insurance brokerage experience, preferred
  • College degree, preferred
  • Excellent verbal and communications skills
  • Must be good with technology
  • Experience with ZOHO, preferred

How to Apply

If you feel you would be a good fit for this role, email your resume and cover letter to jobs@myhealthily.com.

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