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 people, passion and platform are united by our mission: to make employee health & benefits people-friendly again. 



Maestro Health is growing rapidly, and we are looking for a key person to support our sales leadership through this rapid expansion. The Sales Assistant will have a challenging and unique position supporting the sales team, managing all aspects of sales operations. To be successful in this role, you must demonstrate initiative, drive, the ability to effectively multi-task, and a willingness to cheerfully roll up your sleeves and do whatever needs to be done to facilitate the company’s growth and success. 

  • Take initiative, understand our business, and know what it takes for our sales teams to be successful

  • Understand, update, and maintain financial reporting related to sales activity, pipeline, and client activity using and Microsoft Excel

  • Assist with travel, expense reporting and reimbursement

  • Assist with PowerPoint presentation creation and editing as needed

  • Attend sales and management meetings, take minutes and generate notes/reports

  • Assist in planning and coordinating sales-related initiatives and events

  • Handle other ad hoc projects as needed



  • You build relationships and are a pleasure to work with, even when having to hold people accountable

  • No one has to ask twice to get something done, and they are thankful that you have already thought two steps ahead

  • You anticipate the team’s needs and always make sure they are positioned for success

  • You have a great sense of how to build a presentation, along with the ability to create charts and graphics that communicate effectively to an international audience

  • You are the vault of knowledge, and none of it leaves without executive approval and, even then, you may have to eliminate the person you tell

  • You are adaptable and resourceful, able to handle anything that crosses your desk.  You make complex stuff seem simple.

  • You incorporate fun and humor into your everyday activities and make others feel comfortable and at ease

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



  • Hyper organized, capable of handling multiple projects at once, self-motivated, proactive, driven to own the role

  • ·Experience supporting a fast moving, high growth environment as an executive assistant

  • Requires professional experience working with senior level executives within and outside the company as well as clients, vendors and visitors

  • High level of proficiency in grammar, spelling, punctuation and excellent oral communication skills

  • High functioning skills with MS-Word, Excel, and PowerPoint, and You can bend, Excel and PowerPoint to your will.

  • The ability to compose a number of types of professional documents

  • Able to be poised under pressure with a wide variety of individuals, and be able to handle difficult personalities with tact and diplomacy

  • Must have good interpersonal skills, discretion, good judgment, organizational and management ability, initiative and the ability to work independently



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

  • Kashable

  • 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.