Enterprise Cypress Automation Test Architect

Information Technology Chicago, Illinois


Company: Oak Street Health 

Title: Automation Test Architect

Role Description:

Are you enthusiastic about quality and leading individuals to do their best? Do you want to make an impact in both technology and business? Are you skilled in test automation? The Lead Engineer, Test Architect is a technical hands-on leader in the testing organization who is passionate about driving efficiency in the software development process. You provide overall leadership on test strategy, script design, script execution, automation framework, service virtualization, data virtualization, and environment design & advanced Test Management strategies all combined to improve effectiveness, costs and velocity.  

We are currently looking for a talented, experienced Test Architect with technical leadership/communication skills and a passion for testing software for our growing organization.  The Test Architect is responsible for working with leadership to build up core software QA practices for tools, automation, test data, DevOps and infrastructure that align with organizational goals around quality of technology delivery and meet defined metrics and outcomes. The individual will work collaboratively with all levels of leadership and departments to develop, build and maintain automation frameworks, tools, testing strategies, and best practices to be leveraged across all Oak Street Health platforms and systems ensuring high software quality.  

Core Responsibilities:

  • Overall leadership for software quality across the enterprise

  • Provide technical leadership around testing, automation frameworks, best practices and solutions. 

  • Assist with establishing the testing practice for the enterprise. 

  • Provide tooling solutions for any automation limitations.

  • Collaborate with delivery partners to build solutions on testing, automation to achieve CI/CD

  • Provide consultation on the most complex testing and automation strategies.

  • Assess the current state of automation and testing implementations, do a gap analysis and provide strategic direction.

  • Lead automation strategies across multiple applications and multiple testing teams

  • Collaborate with enterprise architect to ensure testable solutions are built following standard engineering practices.

  • Provide technical expertise and ownership in the diagnosis and resolution of issues, including the determination and provision of workaround solution or escalation to service owners.

  • Work with the Development team, QA and DevOps engineers and Product owners in both agile and waterfall methodologies.

  • Document and interact with business and technology stakeholders / team members as necessary.

  • Define and implement metrics and reporting at all phases of PDLC to track quality of software product delivery. 

  • Mentor and develop test engineers on the team

  • Partner with technical team to bring releases to life and ensure they meet our standards.

  • Other duties, as assigned.

What are we looking for?

We’re looking for motivated individuals with:

  • Minimum 10+ years’ experience in automation testing development

  • Strong hands-on, leadership skill, analytical problem-solving skills, quick to learn and adapt

  • Self-motivated, creative problem solver, organized, collaborative with excellent communication skills

  • Application testing experience with hands-on designing, testing complex applications leading into zero/minimum prod issues. Demonstrated ability to translate business requirements into test cases and through to implementation.

  • Deep understanding of design principles, Agile practices, QA theory, Automation practices and tools for consumer facing products and API’s.

  • Experience using Web Service Testing Tools (e.g. SoapUI, Jmeter, K6)

  • Experience with programming languages such as Javascript and test automation frameworks leveraging tools such as Cypress

  • 3+ years hands on experience with implementing Continuous Integration and build automation systems such as Jenkins, Octopus, Azure DevOps etc

  • Experience in architecting, implementing solutions/frameworks for front end and APIs  

  • Excellent coding skills

  • Experience implementing Azure DevOps QA pipelines is a plus.

  • Knowledge of Relational Database Management (Oracle, SQL, MySQL, Mongo db) SQL and Data Validation are essential.

  • Awareness to TDD/BDD approaches and relevant tools such as cucumber.

  • Excellent Communication, Time Management, Reporting and Analytical Skills

  • Experience with application testing in cloud environments

  • Experience with workflow tools and rules engines/processing is a plus.

  • Use of standards for automation testing, documentation, release and configuration management and expertise in CI/CD.

  • Understanding of Performance Testing

  • Strong team ethics and team player.

  • Focus and desire to deliver high quality service.

  • Published and presented technical articles/papers in conferences, journals etc

  • US work authorization

What does being “Oaky” look like?

  • Radiating positive energy

  • Assuming good intentions

  • Creating an unmatched patient experience

  • Driving clinical excellence

  • Taking ownership and delivering results

  • Being relentlessly determined

Why Oak Street Health?

Oak Street Health is on a mission to “Rebuild healthcare as it should be'', providing personalized primary care for older adults on Medicare, with the goal of keeping patients healthy and living life to the fullest. Our innovative care model is centered right in our patient’s communities, and focused on the quality of care over volume of services. We’re an organization on the move! With over 150 locations and an ambitious growth trajectory, Oak Street Health is attracting and cultivating team members who embody “Oaky” values and passion for our mission.

Oak Street Health Benefits: 

  • Mission-focused career impacting change and measurably improving health outcomes for medicare patients

  • Paid vacation, sick time, and investment/retirement 401K match options

  • Health insurance, vision, and dental benefits

  • Opportunities for leadership development and continuing education stipends

  • New centers and flexible work environments

  • Opportunities for high levels of responsibility and rapid advancement


Oak Street Health is an equal opportunity employer. We embrace diversity and encourage all interested readers to apply. 

Learn more at www.oakstreethealth.com/diversity-equity-and-inclusion-at-oak-street-health