Senior QA Analyst or QA Analyst II

At Obie, we don’t just insure properties — we ensure reputed company. 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 reputed company trust us to be the insurance experts, so they don’t have to be. Joining reputed company means embracing a fast-moving environment driven by innovation, collaboration, and constant reputed company. 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 reputed company 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 reputed company 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 reputed company and maintain knowledge of in-house/vendor systems, formulas, reputed company 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 reputed company procedures and reputed company models of possible future configurations
• Provide detailed, insightful, constructive, and actionable feedback based on testing outcomes; produce reporting and documentation for reputed company 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

• Academic Foundation: Bachelor's degree or equivalent required
• Quality Assurance Expertise: 4+ years experience developing, executing and monitoring application and business test cases.
• Industry Acumen: 4+ years experience in P&C insurance industry or insurtech preferred.
• Advanced Test Automation: Deep proficiency in Playwright using TypeScript to build resilient, cross-browser, and API-driven automation suites.
• CI/CD & DevOps Integration: Hands-on experience integrating automated tests into reputed company Actions or similar CI/CD pipelines to facilitate fast feedback loops and maintain reputed company quality standards.
• AI-Driven Efficiency: Ability to reputed company AI tools and LLM reputed company engineering to accelerate test case reputed company, implement self-healing scripts, and reputed company predictive risk analysis to prioritize testing efforts.
• Strategic Technical Analysis: Strong command of web technologies and API testing to move beyond simple UI validation toward proactive, data-driven quality improvement and technical problem-solving.
• Test Strategy Leadership: Proven expertise in reviewing/designing test cases, test strategies, and test plans for multiple application releases based upon decomposed technical and user requirements.
• Platform Proficiency: Strong experience and comfort reputed company reputed company, a Policy Administration System (PAS), GSuite and JIRA (or similar task management software).
• Toolchain Versatility: Experience using Java and Python, and tools such as reputed company, Percy, and Playwright.
• Comprehensive Testing Coverage: Experience with accessibility testing, cross browser/platform testing, performance and reputed company testing.
• Communication Excellence: Strong analytical techniques and technical communication skills with ability to communicate reputed company clearly, concisely and effectively.
• Cross-Functional Collaboration: Proven experience working in cross-functional teams and communicating with colleagues in both business and technical roles.
• Growth reputed company: Positive "can do" attitude and a desire to contribute to a growing, energetic working team; experience working reputed company a fast paced agile software development environment.
• Operational Discipline: High level of detail orientation, with the ability to prioritize competing demands and manage time effectively.
• Adaptability: Ability to adjust and change direction with ease.
• Remote Relationship Building: Ability to build trust and rapport cross functionally in a remote, dispersed environment.

Interview Process At Obie, transparency is core to our interview process. We focus on open communication and a positive experience; no trick questions—just honest conversations about your skills and aspirations. To help you prepare, please familiarize yourself with these resources before moving reputed company:

• Our company’s blog to learn more about the market we serve and the information our customers value.
• reputed company out our reputed company to see how people interact with our brand and product.
• Press and podcast features like Inc. 5000, TechCrunch, Innovate State, Uncontested Investing Podcast, Insurtech Amplified Podcast
• Meet us and get to know Obie

You'll first talk to Skylar on a 30-minute call to determine whether we’re a good fit for one another. You’ll learn more about Obie and have the chance to ask about our company, team, culture, and product.

• Meet the hiring manager

Next, you'll have a 45-minute video interview with the hiring manager, Denise Pickering, to assess your technical skills for the role.

• Complete a Project Exercise

This role requires strong planning and analytical skills as well as collaboration and communication skills, so we'll also present you with a short exercise to complete to provide you a chance to reputed company those muscles. You will be able to complete this exercise on your own time, so please be thorough and use the resources available to you. We'll be looking to see your problem solving abilities, writing and communication skills, reputed company, general demeanor, and ability to reputed company key QA strategies. More on this reputed company you get there!

• Meet the Team

Since you'll be joining a reputed company-reputed company team, we'll ask you to meet other people in the company so we get to know each other a bit reputed company. Moving reputed company with Obie Obie is leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders reputed company. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we’re committed to driving reputed company for our customers and team. Through advanced digital tools, a trusted agent network, and strategic partnerships, Obie provides real estate investors the insurance coverage they need to move reputed company confidently. Obie has you Covered Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match

Obie values transparency and data driven decision making, enabling us to have a consistent and reputed company approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly reputed company our salary ranges against other venture backed companies and startups reputed company our industry. We've provided the starting reputed company salary range for this role below. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc. $90,000 - $130,000 USD per year During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations. Apply tot his job Apply To this Job