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.

While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, PA, SC, SD, TN, TX, UT, WI

Brief Summary of Role

As a QA Analyst II, you will be responsible for collaborating with leaders and stakeholders across the company to understand the business, product and system requirements. Using both business and technical specs, you will create and execute test plans and test cases, and will be responsible for creating and maintaining QA artifacts. The QA Analyst II will provide support for multiple testing phases such as Smoke testing, End to End testing, User Acceptance testing, and Regression testing. 

Those successful in this role will:  

• Be strategic thinkers who are also detail-oriented, organized, and collaborative
• Have the ability to negotiate skillfully with stakeholders to find common ground and acceptable alternatives that satisfy the needs of multiple end users
• Beadaptable in communication style to meet the needs of the intended audience (technical for engineers vs laymans terms for stakeholders vs executive summaries for leaders)
• Be familiar with agile methodologies and the SDLC/STLC for CI/CD

What you'll Do

• 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
• 3+ years experience developing, executing and monitoring application and business test cases; 
• 3+ years experience in P&C insurance industry or insurtech preferred
• 1+ years experience creating test automation suites on web services preferred
• Expertise in reviewing/designing test cases, test strategies, and test plans for multiple application releases based upon decomposed technical and user requirements
• Experience and comfort within Salesforce, a Policy Administration System (PAS), GSuite and JIRA (or similar task management software); 
• Familiarity with Java and Python, and tools such as Postman, Percy, and Playwrite 
• An understanding of 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
• Ability to work in cross-functional teams and communicate 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
• Detail oriented with the ability to prioritize competing demands and manage time effectively
• Ability to adjust and change direction with ease
• 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

1. Intro Chat (30 min.)
A conversation with Skylar to get to know you—and let you get to know Obie.

2. Hiring Manager Interview (45 min.)

You'll get to have a 45-minute video interview with the hiring manager, Denise Pickering. This discussion will be more technical in nature to ensure you have the skills needed to be successful in the role.

3. Take-Home 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 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!

4. Team Interview (1 hour)

Since 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 including 12 week Paid Parental Leave
• Retirement savings plan with company match
• Equity participation opportunities
• Monthly stipends to support a healthy lifestyle and learning and development opportunities

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 full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.

During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.