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 Director of Implementation will be a lead member within our organization that will be responsible for managing and supporting the team that handles the requirements gathering process for the Benefits Administration area of our business.  The implementation team members are responsible for understanding our clients’ business needs and objectives and transforming them into successful outcomes. The team is responsible for initial and ongoing system set up design, benefit product templates, interpretation of SPD’s and other benefit materials that describe our clients’ plan behavior, ongoing process information and communication with the team on the transition of accounts or projects from implementation and beyond.

As we develop and grow as an organization, the Director of Implementation will be responsible for understanding the internal and external business needs for our clients’ implementation process and working to develop tools and efficiencies to help increase quality and scalability.

The position requires strong leadership and mentoring skills, an extensive knowledge of the benefits administration industry, benefit plan design elements, attention to detail, positive professional attitude and the ability to work in a team environment. You will get your hands dirty in our system and know it from beginning to end. Other responsibilities include but are not limited to the following:

  • Manage team of implementation specialists and project managers

  • Coach and mentor team members

  • Analyze current tools and processes and work to improve quality and to gain efficiencies and scalability

  • Understand our software front to back and how it interacts with our clients’ systems and adapt to change and figure out solutions to integration challenges

  • Obtain and analyze product and plan structure, rates and initial data specifications

  • Manage the effective and efficient collection of critical client configuration details for a broad range of insurance categories and products

  • Manage a busy calendar and client communication schedule

  • Coach clients on best practices and assist with system rule and date cycle definitions

  • Create and verify client configuration documentation

  • Communicate clearly with external clients and internal stakeholders to ensure accuracy

  • Work closely with the Development and Build teams to ensure client satisfaction and improve systems features, functionality and performance

  • Identify workflow/process improvements and work with supervisor and operations team to enact change


  • You create and nourish trust and teamwork amongst the team members

  • You are focused and committed to reaching our departmental goals

  • You are prioritizing, executing and ensuring your team’s projects meet all deadlines

  • You create a culture of continuous improvement

  • You learn quickly and apply what you learn to what you do

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


  • Adaptable skills to solve to problems as they arise. Demonstrated ability working in a customer facing software product.

  • Adept at using technology, especially interacting with data formats

  • A friendly, professional demeanor and the ability to excel in a team-oriented environment

  • Strong analytical and detail-oriented aptitude; a high degree of accuracy is required

  • Excellent communication and organizational skills

  • Ability to manage time effectively, set priorities and meet deadlines

  • Ability to learn and adapt to change


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.