Staff Accountant

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

• The Staff Accountant is responsible for targeted activities within the accounting function. This role is responsible for ensuring timely payment of vendor invoices and expense payments, maintaining accurate records, control documentation and reconciliation preparation. This person will be responsible for the complete and accurate recording of accounts payable, accounts receivables and assigned expense accounts. The individual in this role will contribute to the project/department milestones/goals through ownership of assigned accounts. This position will report to the Head of Accounting and Finance. the role and team the candidate will be joining

What you'll Do

• Manages Accounts Payable and Receivable - monitor and reconcile client 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 is preferred
• 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