Infrastructure Engineer

U.S. healthcare today is confusing, inefficient, and expensive. Maestro Health is on a mission to change that.

Our team of Maestronites (Yes, that is what we call ourselves) is revolutionizing not only the way we view health and benefits but also the way we live with our benefits.

We're owned by AXA, and we are growing fast. Really fast. So, we are looking for hard-working, talented, passionate, and like-minded people who want to join us in our mission.

Sound like a team you would love to join? Good news for you: we are hiring.


We are looking for a top-notch infrastructure Engineer to join our team and help drive us to the next level of visibility, efficiency, security, and scale.

  • Experience Operating, monitoring, automation, scaling, and maintaining high availability of our products running in a hybrid on-prem & AWS (Amazon Web Services) cloud environment
  • Familiar with industry operating systems (Windows and Linux) and middleware (App servers, web servers, databases, and others) services.
  • Continually improve processes, tooling of automation, monitoring, scaling, and performance using industry best practice.
  • Troubleshoot infrastructure and application issues, and work with the development team to resolve problems.
  • Identify and improve on points of failure and areas of improvement in the infrastructure and applications.
  • Knowledge of Hypervisors like VMware, Hyper-V, Acropolis (AHV) and network virtualization.
  • Experience with Microsoft 365 (Exchange, SharePoint, and Azure) and on-prem Active Directory services.
  • Participate in blame-free root cause analysis meetings in the event of a production-systems incident so that the team can learn from mistakes, improve our systems, and update or create run books.
  • Continuous review of infrastructure documentation and run books.
  • Plan and perform security patches on our applications and underlying infrastructure.
  • Experience with backup and recovery of systems and data.
  • Participate in the team's production on-call rotation.


  • A successful candidate will be able to drive a project through completion; from taking in initial requirements through design, implementation, documentation, training & testing phases. You will have complete ownership over deliverables with support from the team. Setting realistic timelines and achieving them is a primary Key Performance Indicator.
  • You will stay on top of industry standards, best practices, and current trends so that you can be an expert technical resource.
  • You will develop quality relationships within the team and other departments to help identify pain points and drive progress to eliminate them - the pain points, not the people (well, sometimes the people).


  • Minimum 5 years of production experience in Windows server administration.
  • Minimum 3 years of production on-prem virtualization experience (VMWare, Nutanix, etc.)
  • Knowledge of networking and security principles.
  • Proficient in scripting and developing automation in Python, bash, PowerShell, or similar programming languages.
  • Used to keeping everything you do in source control and automating any task you must do more than once.
  • Comfortable operating in environments subject to regulatory, compliance, and risk-based security requirements.
  • Enthusiastic about innovative technologies and the fresh challenges that come with them.
  • Possesses a service and customer-oriented mindset.
  • Possesses excellent written and verbal communication skills.
  • Able to work within a team and solo with equal success.


  • Familiar with Public Cloud services (Amazon Web Services).
  • Experience in DevOps and Continuous integration & delivery.
  • Working knowledge of ITIL/ITSM and the desire to work in that environment.


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
  • KashableFigo – 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.