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. 


We are seeing growth in the enterprise relationships/voluntary insurance industry so we are adding new positions to our sales team. The Sales Associate - Voluntary Benefits will be responsible for developing relationships and business contacts in their territory and working in conjunction with the Regional Sales Director to drive value and assist in closing new business. Daily responsibilities include but are not limited to:

  • Developing great relationships and understanding the ABCs of sales. We’ll keep the coffee hot.

  • Providing quality consulting services to clients, understanding their needs and pain points and illustrating how Maestro Health can partner to provide those clients with meaningful solutions

  • Delivering value to brokers and clients on industry trends and new Maestro Health products and services

  • Promptly following up on leads and delivering exceptional customer service through inquisitive discovery

  • Identifying new service offerings and collaborating with key organization stakeholders in an effort to expand service and profitability

  • Providing monthly reports of our sales pipeline, forecasts and market analysis

  • Presenting and demonstrating Maestro Health services to a variety of client stakeholders in the executive suite



  • 1-3 years of previous sales and client relationship building experience

  • Bachelor’s degree in business, marketing, HR or equivalent experience

  • Proficient in Microsoft Office applications

  • Excellent communication skills (verbal and written)

  • Voluntary insurance experience

  • Health and Life License is a plus

  • Impeccable listening, analytical, and problem-solving skills

  • Salesforce or CRM experience

  • Ability to negotiate with and influence decision makers


  • Identifying and building relationships with key benefit specialists in your territory

  • Delivering over $350k in new revenue year after year

  • Adding 2 to 3 new clients to your portfolio of business per month

  • Responding to new leads consistently and promptly

  • You are recognized for one of our core values: Fun. Preparedness. Teamwork. Humility. Urgency. Kindness. Bold Thought. Honesty.  


We have great benefits:

  • Paid Time Off

  • Medical and Prescription

  • Dental

  • Vision

  • Life and Disability

  • Health and Wellness programs

  • 401k with Employee Match

  • Figo Pet Insurance

  • Kashable

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, 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 while having fun. 

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.