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:
- Meet us and get to know Obie
You'll first talk to Mary 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 to assess your technical skills for the role. - Complete a Project Exercise
This role requires strong planning, collaboration, and leadership 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 project management strategies. 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
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:
- Competitive salary
- Flexible time off with an encouraged minimum time away to support a healthy work-life balance
- 12 weeks of Paid Parental Leave
- Great health, dental and vision coverage
- Life Insurance
- Flexible Spending & Health Savings Accounts
- Stock Options
- 401k match
- Pet Insurance Reimbursement
- Health and wellness benefit
- Equipment budget - everything you need to do your best work
- Professional development support
- Summer hours
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.