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.
Obie’s insurance production team is seeking a licensed insurance producer to help drive growth and expand our book of business. We’re looking for an innovative, motivated, and results-driven insurance professional who thrives in a fast-paced environment and brings strong insurance knowledge, proven sales skills, and a customer-first mindset.
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:
Obie is a leading insurance platform for real estate investors, combining proprietary technology with a modern insurance experience to simplify Home and Landlord insurance. Today, we serve customers nationwide through direct digital experiences, a growing network of insurance agents, and strategic partnerships with lenders, property management platforms, and real estate technology companies.
As part of The Baldwin Group, one of the nation's leading insurance distribution platforms and a USA TODAY Top Workplace, we're combining the agility of a fast-growing technology company with the scale, resources, and career opportunities of a larger organization as we shape the future of investment property insurance.
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:
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:
45,000 - 70,000 USD per year (Remote (United States))
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 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 three million clients across the country and worldwide.
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.
