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 were 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 a motivated, customer-oriented Site Reliability Engineer. This engineer will be responsible for the health and performance of all server environments, controlling the software release process and bridging gaps between the development, quality assurance and operations teams.

  • Closely monitor the performance of company infrastructure and make recommendations of preventative maintenance or upgrades
  • Quickly respond to and resolve server outages
  • Design and implement automations for routine processes
  • Roll-out new virtual server hardware in the cloud
  • Have an open line of communications with operations to ensure their needs are met
  • Ensure all security and compliance requirements are met
  • Develop and test disaster recovery plans on production environment 
  • Work closely with the software development, quality assurance and operations teams to improve on the software release process
  • Safely deploy software on a regular release schedule with a minimal production environment impact
  • Collaborate with the SRE team and provide code review and sanity checks
  • Provide design reviews and feedback for new and existing systems
  • Build monitors and alerts to ensure the health of critical systems



  • You have a low Average Incident Response Time and Average Incident Resolution Time
  • Your Percentage of Failed Deployments is close to zero
  • You are recognized for one of our core values: Fun. Preparedness. Teamwork. Humility. Urgency. Bold Thought. Honesty. 



  • Bachelor’s degree in information technology, computer engineering or related field
  • 5+ years of experience working in complex computer environments
  • 3+ years working with Linux servers
  • 2+ years working in a SRE/DevOps/SysAdmin or similar role
  • Thorough knowledge of command-line Linux, and a working knowledge of most other operating systems
  • Thorough understanding of the SDLC
  • Knowledge of various SQL languages
  • Familiarity with at least one industry-standard CI tool or framework
  • Experience with server virtualization
  • Proficiency with TCP/IP networks, including secure wireless networks
  • Ability to write scripts in a shell or dynamic language
  • Customer service-oriented attitude
  • Excellent interpersonal communication skills 


  • 2+ years of experience developing software, in any language
  • Experience with at least three CI tools or frameworks
  • Knowledge of web technologies
  • Database administration experience
  • Experience with Amazon Web Services
  • Code testing experience
  • Experience in a customer service or support role



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
  • 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, 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.