Staff Accountant at Obie – Chicago, Illinois

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 Staff Accountant is responsible for targeted activities within the accounting function, including: ensuring timely review/allocation of client payments, carrier reporting and payments, maintaining accurate/updated records, control documentation and reconciliation preparation. The individual in this role will be responsible for the complete and accurate recording of carrier transactions and will contribute to project and department specific milestones and goals.

This position will report to the Accounting Manager.

What you'll Do

• Monitor and reconcile client and carrier accounts to ensure receivables and payables are current and communicate with service team and management as necessary
• Reconcile payment remittances to the billing system of record
• Research and resolve inquiries concerning account status, invoice payments, and refund status
• Responsible for the preparation of Bank, AR, and AP reconciliations
• Responsible for monthly, quarterly, and annual financial statements in accordance with US GAAP
• Assist in the maintenance of a system of internal controls with detailed and targeted documentation of monthly, quarterly, and annual processes
• Provides accounting support to operations

What you'll Bring

• Degree in Accounting/Finance, or related degree or relevant work experience
• 1+ years of relevant work experience
• Excellent verbal and written communication skills
• Maintain a high level of integrity, confidentiality and professional skepticism
• Experience and skilled at working in a collaborative and fast-moving environment

Nice to Haves

• Insurance experience
• Public Accounting experience
• Experience working in Sage Intacct
• CPA

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, Heather, to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong planning, collaboration, and time management skills, so we’ll ask you to complete a short exercise. 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 accounting strategies. 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. This will be a 60-minute video interview.

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 starting base salary range for this role below. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.

$55,016 - $73,355 USD per year

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