Insurance Product Analyst

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, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NY, NC, OH, OR, PA, SC, SD, TN, TX, UT, WI

Brief Summary of Role

We are seeking a strong individual contributor to join our growing insurance product team as an Insurance Product Analyst focused data analysis by analyzing competitive positioning and loss performance to make recommendations for adjustments.

Those successful in this role will have knowledge in the property insurance space, preferably surplus lines, with a passion for driving profitable growth and utilizing insurance expertise to solve challenges.

Additionally, you’ll be self-motivated and directed. An ability to collaborate is a must, but you will be autonomous and expected to succeed without heavy direction and being an expert.

What you'll Do

• Assist the insurance product managers in developing and implementing rate revisions, state expansion, and product development plans that enable Obie to meet our goals
• Leverage analytical and communication skills to collaborate across teams to develop insurance products and services
• Partner closely with Technology Product and Engineering teams to articulate, develop, and validate technology features and enhancements
• Use customer and data insights from the market, our sales funnel, competitors, and claims to inform insurance product development
• Enhance tools, processes, and frameworks to bring insurance products to market

What you'll Bring

• 1-3 years working in a property insurance product management role
• We are looking for someone who has experience with several of the following:
• • forms development, underwriting knowledge, business case development, writing specs for engineering, start-ups, MGA’s, and non-admitted lines
• Knowledge of insurance product management principles, frameworks, and best practices
• Ability to conduct quantitative and qualitative analysis to evaluate performance across various products and segments
• Ability to explain business logic to technical and non-technical team members
• Positive “can do” attitude and a desire to contribute to a growing, energetic work environment
• Detail oriented with the ability to prioritize competing demands and manage time effectively

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