Cloud Operations Engineer

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

Our team of Maestronites (yep, that’s 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’re growing fast. Really fast. So, we’re looking for hard-working, talented, passionate and like-minded people who want to join us on our mission.

Sound like a team you’d love to join? Good news for you: we’re hiring.


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

  • Operate, monitor, automate, scale and maintain high availability of our products, running in a hybrid on-prem & AWS cloud environment
  • Work with team to establish service level objectives and monitor to ensure the objectives are met
  • Continually improve process and tooling of automation, monitoring, scaling, performance, etc.
  • Troubleshoot infrastructure and application issues, and work with the development team to resolve issues
  • Identify and improve on possible points of failure in the infrastructure/applications
  • Execute automation for known cloud-operations tasks, and create new automation for new situations or issues you encounter; automate everything
  • Facilitate blame-free, root cause analysis meetings in the event of a production-systems incident so that the team can learn from mistakes and improve our systems and run books
  • Participate in stress, security, and performance testing
  • Plan and perform security patches on our applications and underlying infrastructure
  • Help secure data and access policies to reduce risk
  • Participate in the team's production via 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'll have complete ownership over deliverables with support from the team. Setting realistic timelines and achieving them is a primary Key Performance Indicator.
  • You'll stay on top of industry standards, best practices, and new trends so that you can be an expert technical resource.
  • You'll 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)
  • You are recognized for one of our core values: CUSTOMER FIRST. INTEGRITY. COURAGE. ONE MAESTRO


  • 5+ years of production experience in both Windows & Linux server administration.
  • 5+ years of production AWS cloud experience.
  • 5+ years of production on-prem virtualization experience (VMWare, Nutanix, etc.)
  • 5+ years of production monitoring/alerting experience.
  • 2+ years’ experience running Kubernetes in production.
  • Experience with modern DevOps engineering practices.
  • Versed in infrastructure and config as code practices using technologies like Terraform, CloudFormation, Ansible, etc.
  • 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 have to do more than once.
  • Comfortable operating in environments subject to regulatory, compliance, and risk-based security requirements.
  • Enthusiastic about cutting-edge technologies and 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.
  • Working knowledge of ITIL/ITSM and the desire to work in that environment a plus.


We have great benefits:

  • Generous PTO
  • 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, laugh, work your tail off 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.