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
- 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 GitHub Actions or similar CI/CD pipelines to facilitate fast feedback loops and maintain continuous quality standards.
- AI-Driven Efficiency: Ability to leverage AI tools and LLM prompt engineering to accelerate test case generation, implement self-healing scripts, and perform 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 within Salesforce, a Policy Administration System (PAS), GSuite and JIRA (or similar task management software).
- Toolchain Versatility: Experience using Java and Python, and tools such as Postman, Percy, and Playwright.
- Comprehensive Testing Coverage: Experience with accessibility testing, cross browser/platform testing, performance and security testing.
- Communication Excellence: Strong analytical techniques and technical communication skills with ability to communicate ideas 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 Mindset: 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.
- 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 forward:
- Our company’s blog to learn more about the market we serve and the information our customers value.
- Check out our LinkedIn 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 ObieYou'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 managerNext, 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 ExerciseThis 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 flex 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, empathy, general demeanor, and ability to leverage key QA strategies. More on this when you get there!Meet the TeamSince you'll be joining a close-knit team, we'll ask you to meet other people in the company so we get to know each other a bit better.Moving Forward with Obie
Obie is leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders nationwide. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we’re committed to driving progress 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 forward 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 equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the starting base 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 yearDuring your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.
