Insurance Program 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.

Brief Summary of Role

The Insurance Program Analyst will play a critical role in helping Obie build, manage, and optimize the insurance programs that drive our business.

Reporting to the Head of Rev Ops and Analytics, this role sits at the intersection of insurance, analytics, technology, and business strategy. You'll use data, SQL, AI, and business intelligence tools to understand product and portfolio performance, support product development and expansion, and help turn complex insurance questions into clear insights and action.

This is an opportunity for someone who enjoys getting into the details, solving problems, and seeing their work directly influence business decisions. The right person will bring strong technical skills, insurance curiosity, business judgment, and a willingness to take ownership from question through execution.

What you'll Do:

Analyze and Improve Insurance Program Performance

• Analyze insurance product and portfolio performance to identify trends, opportunities, and areas requiring attention.
• Support insurance product managers and program leaders with rate revisions, state expansion, product development, and other strategic initiatives.
• Conduct quantitative and qualitative analysis across products, states, customer segments, and other areas of the business to support profitable growth.
• Help translate portfolio performance into clear recommendations and actions.

Turn Data Into Insight

• Build and maintain dashboards, reporting, and analytical tools using Sigma and other business intelligence platforms.
• Develop and refine metrics that help the Insurance Programs team understand product performance, operational efficiency, and business outcomes.
• Answer complex reporting, metric, and data questions for insurance stakeholders across the organization.
• Perform data quality checks, reconciliations, and validation to ensure teams can confidently make decisions using the data available to them.

Build the Future of Insurance With Technology and AI

• Use AI tools, including Claude, to improve analytical processes, build more effective tools and frameworks, and accelerate how insurance products are developed and brought to market.
• Partner with Product, Engineering, Data, and Insurance teams to identify opportunities to automate work, improve workflows, and create better decision-making tools.
• Bring curiosity and experimentation to how emerging technology can improve the way Obie operates.

Partner Across the Business

• Work closely with Insurance Product Managers, Underwriting, Compliance, Data Engineers, Data Analysts, Distribution, and other business partners to solve complex problems.
• Translate technical analysis and business logic into clear, actionable insights for both technical and non-technical audiences.
• Serve as a trusted resource for insurance stakeholders seeking to better understand data, metrics, and performance.
• Help build a culture of data literacy and evidence-based decision-making across the Insurance organization.

What you'll Bring:

Insurance and Business Acumen

• 1–3 years of experience in an analytics, insurance, underwriting, product, or related role within the property insurance industry.
• Experience with or knowledge of surplus lines insurance is strongly preferred.
• Understanding of insurance product principles and the factors that influence product and portfolio performance.
• Interest in using data to solve business problems and support profitable growth.

Technical and Analytical Skills

• Experience using SQL to analyze and work with data.
• Experience with data visualization and business intelligence tools; Sigma experience is a plus.
• Ability to conduct quantitative and qualitative analysis and turn findings into clear business recommendations.
• Curiosity and enthusiasm for using AI and emerging technology to improve how work gets done.

Collaboration and Ownership

• Ability to explain complex business logic and analytical findings to both technical and non-technical audiences.
• Strong ownership mindset with the ability to move from identifying a problem to helping drive a solution.
• Comfortable working across teams and with stakeholders at all levels of the organization.
• Detail-oriented with the ability to manage competing priorities and maintain a high standard of quality.

You'll thrive in this role if you:

• Are naturally curious and enjoy figuring out how things work.
• Don't stop at identifying a problem—you want to help solve it.
• Can move comfortably between detailed analysis and big-picture business questions.
• Enjoy collaborating with people who have different areas of expertise.
• Are comfortable with ambiguity and willing to learn as the business evolves.
• Use data to challenge assumptions while applying sound business judgment.
• Care about the quality of your work and take pride in making the people around you more effective.

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. Meet us and get to know Obie
   You'll first talk to Kara 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.
2. Meet the hiring manager
   Next, you'll have a 45-minute video interview with the hiring manager, Sam Isken, to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong technical, analytical and communication skills, so we’ll ask you to complete a short exercise to flex those muscles. You can take your time and use the resources available to you. More details will come when you reach this step!
4. Meet the Team
   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
• 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 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.