Plan Document Specialist

We are… an employee health & benefits company with a tech-meets-service platform that simplifies and personalizes how employees and employers’ shop, enroll and live with their benefits. Our innovative technology makes it easy for employees to choose the right benefits plan while equipping HR with the tools they need through one partner, one service team, one platform, one portal.

Maestronites are… brought together with a passion to disrupt the status quo by reimagining employee health and benefits. This passion has driven us to create the first complete platform that optimizes the entire benefits experience for everyone. Our people, passion and platform are united by our mission: to make employee health & benefits people-friendly again.


The Plan Document Specialist supports the implementation of new clients and maintenance of existing clients under the supervision of our Director of Plan Consulting. The ideal candidate should possess a strong background that includes knowledge of Employee Benefits, ACA/CAA regulations as well as ERISA regulations.

  • Drafting Summary of Benefits & Coverage
  • Drafting Plan Documents utilizing a checklist style input
  • Drafting plan amendments
  • Manage ticket requests adhering to deadlines and work within allotted timeframes
  • Assist with ongoing department projects
  • Participates in industry-related continuing education offerings


  • Demonstrate accountability and integrity
  • Tackle tough assignments with initiative, creativity, a value-added mind-set, questioning nature, and a sense of urgency
  • You juggle multiple priorities and projects meeting all deadlines
  • You learn quickly and apply what you learn to what you do
  • You are recognized for one of our core values: Customer First. Integrity. Courage. One Maestro.


  • Degree preferred or equivalent combination of education, training or experience
  • Maintain a current knowledge of applicable ERISA, and ACA/CAA regulations
  • Detail oriented with excellent organizational skills
  • Thoroughness and follow-through
  • Strong verbal and written communication skills
  • Ability to prioritize and manage multiple tasks and activities
  • Ability to function in a high volume setting with tight deadlines
  • Research skills; strong analytical and problem-solving skills
  • Talent for quickly learning new tasks
  • Ability to work calmly under pressure
  • Strong character, team player, flexible
  • Strong understanding of principles of risk management and quality assurance
  • Excellent computer skills with a strong competency in Microsoft Office Apps


We have great benefits:

  • Personal, Vacation and Sick Time
  • Medical and Prescription
  • Dental
  • Vision
  • Life and Disability
  • Health and Wellness programs
  • 401k with Employee Match
  • Kashables
  • Figo – Pet Insurance

We have great perks in each of our offices, along with a fun, energetic and fast-paced environment, and what will really drive you is our vision. Maestro Health is making employee health & benefits people-friendly again by making healthcare easy to understand, tools easy to use, and costs easy to control. We are aiming to become a household name within the employee health & benefits space.

We can’t do that without great people. We want to hear “WOW! That was the best job and business experience I ever had!” from every Maestronite – past, present, and future. You should be personally challenged, laugh, work your tail off and look forward to coming to work.

Are you ready to become a Maestronite? Let’s do this.

Maestro Health is an equal opportunity workplace. We are committed to equal opportunity regardless of race, color, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, or veteran status.