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 VP of Compliance personifies the Maestro Health culture to employees, clients and business partners.  As a direct report to the Chief Compliance Officer, you will serve as a Brand Ambassador for our culture and company, rolling up your sleeves to get things done. Specifics include a variety of compliance leadership initiatives, including but not limited to:

  • Overseeing and leading various aspects of our compliance and ethics programs

  • Partner with leaders to identify and mitigate risk exposure as compliance vulnerability and risk within the organization

  • Establish and maintain compliance oversight and monitor structures with robust reporting capabilities and training programs

  • Foster collaboration across the business with subject matter expertise

  • Serve as compliance lead for internal audit and external regulatory audits

  • Provide day-to-day leadership and support to the Chief Compliance Officer and executive team

  • Attending, and often leading, a variety of compliance and Maestro Health meetings

  • Traveling as needed but not excessively


  • The CCO, executive leadership and compliance team have a high level of confidence in you

  • Compliance programs are fully developed, administered and demonstrate organizational value

  • The compliance team rocks; successfully execute and share their knowledge

  • Effectively communicate inside and outside of the organization

  • You are recognized as demonstrating our core values: Fun. Preparedness. Kindness. Teamwork. Humility. Urgency. Bold Thought. Honesty.   


  • Rock solid integrity and ethics. These are non-negotiables.

  • Bachelor’s degree and 10 years of compliance leadership experience, or similar combination of education and experience in healthcare or other highly regulated environment

  • CPCO and CEBS certifications desired

  • Broad expertise in the compliance field, compliance program design and audit response with demonstrated strategic business savvy

  • Ability to interpret regulations and laws and disseminate the information

  • Successful track record managing high performing teams

  • Extensive knowledge of both fully insured and self-insured employee benefit plans

  • High degree of emotional intelligence and people skills. If you don’t know what that is, this isn’t the job for you.


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.