Software Engineer (Test Automation)

iManage•Chicago, IL

4d•$80,000 - $100,000•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

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)

Responsibilities

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

Benefits

Flexible work hours
Supportive, experienced team with an inclusive, encouraging, and vibrant culture
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
Internal development framework for career path ownership
Access to unlimited courses in LinkedIn Learning
Innovative, industry leading SaaS company that is continuing to grow & scale
Inclusive environment where employees can shape the culture
Market competitive salary
Annual performance-based bonus
Comprehensive Health/Vision/Dental/Life Insurance
401k Retirement Savings Plan with a company match up to 4%
HealthJoy, a healthcare concierge service
Enhanced leave for expecting parents; 20 weeks 100% paid for primary leave, and 10 weeks 100% paid for secondary leave
Flexible time off policy
Company wellness days
Free access to the Healthy Minds app