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. 



Maestro Health is looking for an intelligent, ambitious, thorough and detail-oriented person for the role of Project Manager/Scrum Master. Your primary role is to shepherd projects through to successful completion while coordinating resources, establishing timelines and identifying risks. You will work closely with stakeholders across our organization to ensure the efficiency and effectiveness of solutions deployed in support of business goals and objectives. Daily responsibilities include but are not limited to:

  • Manage all aspects of the project management lifecycle for multiple simultaneous projects

  • Facilitate project initiation by gathering & analyzing requirements, identifying stakeholders and establishing project objectives

  • Manage multiple concurrent sprints across multiple projects, lead retrospectives and sprint planning meetings

  • Deliver agile methodology process improvement across all projects

  • Design processes that promote simplicity, efficiency, scale and control

  • Identify and measure KPIs to drive project success

  • Identify continuous improvement opportunities and drive operational excellence

  • Motivate project stakeholders throughout the life of the project to maintain peak performance, momentum and quality

  • Identify and elevate risks to project stakeholders and develop mitigation strategies prior to becoming an issue

  • Communicate timely project status to the organization through different channels (e.g. dashboards, reports and meetings)

  • Provide input and recommendations to continue evolving the organization’s project management approach


We do not simply manage projects to fruition, but rather to a successful, exciting launch. You are responsible for not only keeping the project tasks on schedule but also keeping the team motivated through the end of the project to ensure a follow through.

As you become a part of the Maestro Health organization, it is important for you to build relationships and trust with your fellow Maestronites so that you can be effective in this role. We expect that in a very short time you will be recognized for exuding our core values: Fun. Preparedness. Teamwork. Humility. Urgency. Kindness. Bold Thought. Honesty.

Projects are an opportunity to learn as much as they are to execute and deliver.  You are charged with reacting to information quickly and continually improving your approach.


To perform this job successfully, an individual must be able to perform each essential duty masterfully. The requirements listed below are representative of the knowledge, skill, and/or ability required.

  • 3+ years of professional experience using Agile Methodologies to drive success across multiple concurrent projects

  • Confidence driving stand-ups, retrospectives and sprint planning meetings 

  • Excellent verbal and written communication skills and the ability to interact professionally with a diverse group - executives, managers and subject matter experts

  • Interviewing skills with the ability to talk with individuals and groups about their needs and ask the right questions to surface essential requirements

  • Listening skills with the ability to understand what people say and to detect what they might be hesitant to say

  • Analytical skills with the ability to critically evaluate the information gathered from multiple sources, reconcile conflicts and decompose high-level information into details

  • Observational skills with the ability to validate data obtained via other techniques and expose new areas for elicitation

  • Diplomatic skills with the ability to communicate respectfully and tactfully with project stakeholders to resolve conflicts


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 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.