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. 



Maestro Health is growing, and we are looking for great QA Automation Architect to join our Chicago office. We need someone to join the team to help us create a test automation framework from the ground up. Quality is a very important part of our work, and we want someone with a passion for testing software applications to be part of our team. Daily responsibilities include but are not limited to:

  • Help identify tools, frameworks and processes for automation of our software testing

  • Implement and automate framework to help us accelerate our new feature testing as well as regression test cycles

  • Work with our development teams to provide top QA testing for our applications

  • Troubleshoot and resolve reported issues related to the automation system

  • Collaborate with diverse project members, voice your opinion and contribute to a high performing team


  • Experience with desktop apps across multiple devices and screen sizes

  • Relational database experience

  • Coding experience in a language similar to Python, C# or Java

  • Web service experience (both SOAP and REST)

  • Web page automation experience (including single page and session-based applications)

  • Continuous integration experience with systems like Hudson, Jenkins, Circle CI or Wercker

  • Experience working in both an Agile and Waterfall development environment

  • Experience with White Box and Black Box testing approaches

  • Experience with ticket tracking systems and testing systems such as Jira, QTP, Team Foundation Server, Selenium, Mercury or Rational

  • A team-centric style, great attitude and energy and a passion for testing and quality

  • Ability to teach others to write tests which can be executed automatically

  • Strong written and verbal communication skills

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



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.