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
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IMPORTANT NOTICE:
This position description is intended to describe the level of work required of the person performing in the role and is not a contract. The essential responsibilities are outlined; other duties may be assigned as needs arise or as required to support the organization. All requirements may be subject to reasonable accommodation to applicants and colleagues who need them for medical or religious reasons.
Click here for some insight into our culture!
The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.
The Baldwin Group Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about The Baldwin Group and has not been reviewed or approved by The Baldwin Group.
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Healthcare Strength — Health coverage includes flexible medical options, 24/7 telemedicine, mental health support, company‑paid life and disability, plus dental and vision. Feedback suggests these comprehensive offerings contribute meaningfully to total rewards.
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Leave & Time Off Breadth — Time‑off programs span parental leave, paid holidays, paid sick days, and flexible PTO, with some teams citing unlimited PTO. Feedback suggests flexible PTO depth is a valued element of the package.
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Equity Value & Accessibility — Equity grants are provided to all new hires. Feedback suggests broad‑based equity can enhance perceived fairness and long‑term value.
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What We Do
BRP is now The Baldwin Group! We’ve updated our name to reflect our unified group of talented teams across the country. The Baldwin Group is a cohesive group of experts in business insurance, employee benefits, retirement planning, and all areas of private and personal insurance. Since our founding in 2011, we’ve evolved from a local business into a national firm with a vast network of specializations and industry practices for the benefit of our more than two million clients across the country. In addition, we have built excellent relationships with a wide range of insurance company partners. These relationships, coupled with our entrepreneurial and family-oriented culture, and deep expertise enable us to seamlessly deliver a breadth of innovative solutions to clients. At The Baldwin Group, we help provide the solutions our clients need to have confidence and gain peace of mind as they pursue what’s possible for themselves, their families, and their businesses. Whether they are renting their first apartment or buying a larger home, opening a small business or taking their company public, we offer solutions to support them on every step of their journey. This has been our story since the beginning—we provide the indispensable expertise and quality insights that give our clients peace of mind to pursue their purpose, passion, and dreams. And that’s what The Baldwin Group will continue to do for years to come: we Protect the Possible℠.
