Software Tester Jobs in Chicago, IL (NOW HIRING)

We offer a flexible working policy that supports a healthy balance between personal and professional well-being. This role requires in-office presence on Tuesdays & Thursdays to collaborate, connect, and learn from peers - while also maintaining the flexibility for meaningful work-life balance.

Being a Software Engineer at iManage Means…

iManage runs on trust in every release. Our automated test engineering team is what keeps that trust intact by building the frameworks that catch problems before customers ever see them. We are looking for a Software Engineer to join this team and help build out the automation that validates our desktop applications on Windows.

You are comfortable with Python scripting, debugging flaky tests, and picking up new tools as the job requires. You will make meaningful contributions from day one, whether you are new to test automation or have a couple of years of hands-on experience.

iM Responsible For…

• Designing, developing, and maintaining automated test scripts using Python for desktop application testing on Windows
• Building and executing UI automation test suites using tools such as WinAppDriver or Appium for Windows desktop applications
• Provisioning, configuring, and managing Azure virtual machines to support scalable, repeatable test execution environments
• Integrating automated test suites into GitHub Actions workflows for continuous integration and continuous testing
• Writing and maintaining PowerShell scripts to support environment setup, configuration, and test automation on Windows
• Developing and maintaining test cases using pytest or unittest frameworks
• Identifying, documenting, and tracking defects, and collaborating with development teams to reproduce and resolve issues
• Analyzing test results and CI pipeline logs to diagnose failures and flaky tests
• Participating in code reviews for test automation scripts and contributing to improving test framework architecture
• Maintaining clear documentation of test plans, test coverage, and automation framework usage
• Collaborating with QA, development, and DevOps teams to ensure test coverage aligns with product requirements and release schedules

iM Qualified Because I Have…

• A bachelor's or master's degree in computer science or a related field
• 2+ years of experience in software testing or test automation
• Working knowledge of Python for scripting and test automation
• Familiarity with Windows operating systems and desktop application behavior
• Exposure to or working knowledge of Azure virtual machines, including provisioning, configuration, and remote access
• An understanding of CI/CD concepts, with hands-on or academic exposure to GitHub Actions or similar tools such as Jenkins or Azure DevOps
• Comfort working alongside AI coding assistants (e.g., Claude, GitHub Copilot) as part of the daily development and testing workflow
• An ability to critically evaluate AI-generated code and test output rather than accepting it at face value — you verify, don’t just trust
• Basic PowerShell scripting ability
• Familiarity with pytest or unittest, or a willingness to learn quickly
• Strong analytical and debugging skills
• Good written communication for documenting test cases, defects, and results

Bonus Points If I Have…

• Hands-on experience with WinAppDriver, Appium, or similar UI automation frameworks for desktop applications
• Experience working with version control systems such as Git and GitHub
• An understanding of software testing methodologies, including functional, regression, smoke, and integration testing
• Curiosity about applying AI/LLM-based tooling to test automation problems — for example, generating test cases from requirements, summarizing flaky-test patterns, or auto-triaging CI failures
• Hands-on experience with cloud platforms (Azure, AWS, or GCP)

Don't meet every qualification listed above? Studies show that women and people of color are less likely to apply to jobs unless they meet all qualifications. At iManage, we are committed to building a diverse and inclusive environment, and encourage everyone to show up as their full authentic selves. We welcome those that come with a growth mindset and a hunger for learning; so, if you are excited about this role but your past experience doesn't align perfectly with every qualification we encourage you to apply anyways!

iM Getting To…

• Join a supportive, experienced team with an inclusive, encouraging, and vibrant culture.
• Have flexible work hours that allow me to balance my ‘me time’ with my work commitments.
• Collaborate in a modern open plan workspace, with a gaming area, free snacks, drinks and regular social events.
• Focus on impactful work, solving complex, real challenges utilizing the latest technologies and protocols.
• Own my career path with our internal development framework. Ask us more about this!
• Learn new skills and earn certifications with access to unlimited courses in LinkedIn Learning.
• Join an innovative, industry leading SaaS company that is continuing to grow & scale!

iManage Is Supporting Me By...

• Creating an inclusive environment where I can help shape the culture not just by fitting in, but by adding to it.
• Providing a market competitive salary that is applied through a consistent process, equitable for all our employees, and regularly reviewed based on industry data.
• Rewarding me with an annual performance-based bonus.
• Offering comprehensive Health/Vision/Dental/Life Insurance, and a 401k Retirement Savings Plan with a company match up to 4%.
• Giving access to HealthJoy, a healthcare concierge service, to help me maximize my health benefits.
• Granting enhanced leave for expecting parents; 20 weeks 100% paid for primary leave, and 10 weeks 100% paid for secondary leave.
• Providing me with a flexible time off policy to take the time off that I need. Be it for vacation, volunteering, celebrating holidays, spending time with family, or simply taking time to recharge and reset.
• Caring for my mental health and well-being with multiple company wellness days and free access to the Healthy Minds app for mindfulness, meditation and more.

About iManage…

iManage is dedicated to Making Knowledge WorkTM. Over one million professionals across 65+ countries rely on our intelligent, cloud-enabled, secure knowledge work platform to uncover and activate the knowledge that exists inside their business content and communications.

We are continuously innovating to solve the most complex professional challenges and enable better business outcomes; Our work is not always easy but it is ambitious and rewarding.

So we’re looking for people who love a challenge. People who are happiest when they’re solving problems and collaborating with the industry’s best and brightest. That’s the iManage way. It’s how we do things that might appear impossible. How we develop our employees’ strengths and unlock their potential. How we find meaning in everything we do.

Whoever you are, whatever you do, however you work. Make it mean something at iManage.

iManage provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.

Learn more at: www.imanage.com

Please see our recruitment privacy statement for more information on how we handle your personal data.

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