Senior Sales Analyst

 U.S. healthcare today is confusing, inefficient and expensive. Maestro Health is on a mission to change that by making health and benefits people-friendly again. Not only are we changing the way we view health and benefits, but also the way we shop, enroll, and live with our benefits using a tech-meets-service approach.  


An integral component of our market-facing Sales efforts, this position works hand in hand with the field Sales Directors to ensure delivery of timely and high-quality proposals to our new business prospects and enhances the Broker/Client relationships.

  • Working in tandem with assigned Sales Director(s) on all stages of an opportunity from start (prospecting) to finish (closed won).
  • Review all quote requests, inclusive of questionnaires to ensure all data is complete for submission. Work with the consultant/broker on missing items and complete quote request document.
  • Using RFP 360 for questionnaires, when needed collaborate with other department leads for answer(s).
  • Complete pricing for solution of services with Sales Director approval.
  • Ensure Salesforce is up to date with all prospects, brokers, opportunities and closed deals along with identify the proper stage of a deal.
  • Work closely with stop loss unit and maintain open communication with the Sales Director to inform on delivery dates, missing data and if there are any declines to quote.
  • Create and finalize proposals for Sales Director to deliver. This includes requesting needed reports with Network partners, Pharmacy Benefit Managers and other vendors Maestro offers.
  • Provide any relevant marketing materials to help the Sales Director.
  • Coordinating and planning any meetings that the Sales Director attends or hosts. This includes site visits, broker events or meeting and finalist meeting for prospects. Provide all post meeting deliverables and/or follow-ups after the meeting.
  • For new sales, request and complete the needed documentation. This includes but not limited to letters of Intent, disclosure statements, completion of scope of services document, contract request and new group forms for specified networks and services.
  • Coordinate handoff from Sales to Implementation.
  • Identify appropriate network strategy and understand network access geographically.
  • Understand the funding mechanics behind self-funding and have the ability to help educate prospects.
  • Ability to review proposal and provide a write up outlining competitive advantage for the seller to send when delivering the proposal.
  • Coordinating with broker offices and clients as part of the Sales team.


  • You will complete sales documentation from the prospect stage to a closed won stage.
  • You handle completion of proposals for delivery to broker ensuring consistently competitive positioning.
  • Working with our vendor partners (for example, networks, PBM’s, RBP vendors) to request the necessary information that needs to be included in our proposal.
  • You will coordinate and deliver all requested documents, proposals, reports and quotes on time.
  • Maintain the accuracy of Salesforce and ensuring timely updates to pipeline stages.
  • You will be responsible for ensuring you are up to date on all Maestro products and services.
  • You are client-focused and you have a passion to exceed all prospects, brokers and customers’ expectations.
  • Ensuring your Sales Directors have successful client engagements from initial meeting coordination to any deliverables after the meeting.
  • You contribute to Maestro revenue growth and provide recommendations for additional services (or vendors) to gain additional revenue.


  • 5+ years experience in broker or client-facing role
  • You are well organized and can think quickly and pivot if necessary
  • You have great time management skills and the ability to multitask
  • Preferably have knowledge of Salesforce
  • You understand the mechanics of a Self-funded Medical Plan
  • Experience working in a fast-paced Sales environment
  • You are professional and have good people skills
  • Proficient in Microsoft Office Suite
  • Proficient in Adobe Acrobat Pro
  • You are an effective communicator in written correspondence and in verbal conversations.
  • You have the skills needed to proactively educate across teams and clearly articulate timelines, milestones, challenges, capabilities and/or limitations
  • Ability to prioritize prospect needs


  We have great benefits:    

  • Generous PTO
  • Medical and Prescription 
  • Dental 
  • Vision 
  • Life and Disability 
  • Health and Wellness programs 
  • 401k with Employee Match 
  • FSA / HSA / Dependent Care
  • Kashable 
  • Figo – Pet Insurance 
  • LegalShield

Maestro Health offers many other perks! We also offer a fun, energetic, and fast-paced environment, but what will really drive you is our mission. We are on a mission to humanize employee health and benefits while lowering costs and improving outcomes. Isn’t that a mission we can all get behind?

Maestro Health believes that better benefits exist. We believe the healthcare system should be easy to navigate. We believe that health and benefits should come at a fair and reasonable cost. Our goal is to become a household name within the employee health & benefits space.  

We can’t do that without great people! Maestronites thrive from the innovative culture and work we get to do every day to support our clients. Our tech-meets service approach to self-funded benefits starts and ends with people. Great people, like you!

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