Senior QA Analyst or QA Analyst II

Obie
Chicago, IL$90k – $130kPosted 30 March 2026

Job Description

Senior QA Analyst or QA Analyst II At Obie, we don’t just insure properties — we ensure progress. With advanced technology, real-time data, and a vast network of agents and partners, we help real estate investors and landlords get insurance coverage whenever and wherever they need it. Thousands of owners nationwide trust us to be the insurance experts, so they don’t have to be. Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, and celebrate wins together. If you're passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you. Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays. Brief Summary of Role The Senior QA Analyst is responsible for working with cross-functional subject matter experts to document, deploy and monitor business and application test cases. This position will require the crafting and deployment of testing strategies and the presenting of strategic findings to leadership to move the organization to action. Those successful in this role will be strategic thinkers with the ability to negotiate skillfully with stakeholders to find common ground and acceptable alternatives that satisfy the needs of multiple end users. Additionally, you will help drive overall strategy and prioritization of work efforts. What you'll Do Be responsible for collaborating with leaders and stakeholders across the company to understand the business, product and system requirements. Thoroughly test software to ensure proper operation and freedom from defects utilizing knowledge of application architecture Maintain documentation of test results, assist in debugging and communicate to business stakeholders Utilize necessary analytical skills to develop and maintain knowledge of in-house/vendor systems, formulas, rate specifications, manual rules, and state filing information to identify unusual, inconsistent or error conditions Maintain a test repository and/or performance test results; identify and resolve problems in areas of test development/management; devise improvements to current procedures and develop models of possible future configurations Provide detailed, insightful, constructive, and actionable feedback based on testing outcomes; produce reporting and documentation for all testing efforts, results, activities, data, logging and tracking Create visibility and deepen collaboration during development to ensure more reliable releases Enhance tools, processes, and frameworks to bring insurance products to market What you'll Bring Bachelor’s degree or equivalent required 4+ years experience developing, executing and monitoring application and business test cases 4+ years experience in P&C insurance industry or insurtech preferred 2+ years experience creating test automation suites on web services preferred Proven expertise in reviewing/designing test cases, test strategies, and test plans for multiple application releases based upon decomposed technical and user requirements Strong experience and comfort within Salesforce, a Policy Administration System (PAS), GSuite and JIRA (or similar task management software) Experience using Java and Python, and tools such as Postman, Percy, and Playwrite Experience with accessibility testing, cross browser/platform testing, performance and security testing Strong analytical techniques and technical communication skills with ability to communicate ideas clearly, concisely and effectively Proven experience working in cross-functional teams and communicating with colleagues in both business and technical roles Positive “can do” attitude and a desire to contribute to a growing, energetic working team; experience working within a fast paced agile software development environment High level of detail orientation, with the ability to prioritize competing demands and manage ti ... (truncated, view full listing at source)
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