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: FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, PA, SC, SD, TN, TX, WI. For this position, we are looking for someone located within Eastern or Central timezones.

Brief Summary of Role

We are seeking an individual to join the Data Analytics team at Obie. Those successful in this role will have data analytics experience, finance and accounting reporting skills, and experience in P&C insurance. Those successful will also have stellar interpersonal skills and be comfortable communicating both within the data analytics team and with leadership across the company.

What you'll Do

• Perform daily data quality checks of all critical data sets and recommend required changes to the data (and potentially systems creating the data)
• Perform reconciliations between different critical data sets that contain similar data to identify and explain any discrepancies to VP of Finance
• Perform daily updates to our external reporting datasets to ensure data is accurate and complete
• Answer data quality/reconciliation questions from other departments and produce findings to the data team and inquiring party
• Lead data team automations, such as the implementation of data quality tools/automated data quality checks

What you'll Bring

• 2+ years of experience in data analytics, or an adjacent field
• Familiarity with accounting principles and financial reporting required
• Insurance experience required
• Strong SQL experience required
• Strong interpersonal and communication skills
• Strong time management skills and ability to manage competing priorities

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 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.
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 planning, collaboration, communication, and analytical 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. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and how well you apply key data analytics principles. 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 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.