Data Analyst R Programming Jobs in Chicago, IL (NOW HIRING)

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.

We are seeking an analytics individual to join the growing Revenue Operations (RevOps) and Analytics department’s Business Insights team at Obie. Those successful in this role will have a good mix of technical skills (SQL, python, data visualization, AI), business acumen, and insurance or financial services knowledge.

Strong ownership abilities and interpersonal skills are critical for the individual in this role. At the same time, they will be a team player who is comfortable collaborating within the analytics team and across departments, from individual stakeholders to executives. The person in this role must be a doer who can strategize through problems, have the flexibility to adapt to whatever is most critical, and have the technical skills and discipline to execute.

• Develop hypotheses to understand the state of the business, such as drivers of growth or stagnation
• Build and maintain dashboards / reports within our Business Intelligence / Data Visualization tool Sigma
• Align and support various analytics, metrics, data, and reporting needs at Obie across various departments like Growth & Channel Distribution, Product & Engineering, Insurance, Finance & Accounting, and the Executive team in collaboration with Data Engineers, Insurance Product Analysts, and Operations Analysts
• Support financial budgeting, forecasting, and tracking
• Perform data quality checks and reconciliations to datasets as needed
• Serve as a trusted advisor to all stakeholders of data, answering reporting, metric, and data questions, and facilitating a culture of data literacy and data-driven decision making

• Experience in data analytics or business analytics with strong SQL abilities
• Knowledge and interest in insurance
• Ability to drive initiatives start to end and manage competing priorities
• Ability to dive deep into the data and details while synthesizing the bigger picture for stakeholders
• Strong interpersonal, communication, and leadership skills
• Team player attitude with the desire to drive impact at a fast growing company

• Experience in insurance, financial services, or similar
• Experience with another analytics tool like python, R, or similar
• Experience working with AI (We use Claude), github, and dbt
• Experience in strategy, operations and analytics, GTM analytics, financial forecasting, consulting, or similar

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.
• 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.
• Meet the hiring manager
  Next, you’ll have a 45-minute video interview with the hiring manager, Claire Wang , to assess your technical skills for the role.
• Complete a Project Exercise
  This role requires strong analytical abilities and leadership skills, so we’ll ask you to complete a short exercise to flex those muscles. You can take your time and use resources available to you, however, we ask that you limit usage of AI when it comes to solving the problem, so we can best understand how you think through problems. We’ll primarily be assessing your technical skillset, problem solving abilities, and communication skills. More details will come when you reach this step!
• 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

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.

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:

• 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.

The pay range for this role is:

70,000 - 90,000 USD per year (Remote (United States))