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Insurance Specialist

Obie - Chicago, IL, United States - Hybrid - posted 2026-10-08

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Obie is a leading insurance platform for real estate investors, combining proprietary technology with a modern insurance experience to simplify home and landlord insurance. The company serves 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, Obie combines the agility of a fast-growing technology company with the scale and resources of a larger organization. In this role, you will be a licensed insurance producer helping to drive growth and expand the book of business. You will take in sales leads, determine which type of policy will be needed, and effectively quote business (no cold calling required). You'll utilize Salesforce to track and manage new sales leads and metrics, conduct proactive and diligent client follow-up, follow underwriting guidelines and carrier standard operating procedures, and demonstrate mastery of diverse policy types including Builders Risk, Landlord (short-term and long-term), commercial property, General Liability, and Flood. Obie is seeking 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. Chicago-based employees are hybrid and expected to be in office on Tuesdays and Thursdays. The company values transparency and data-driven decision making, with a consistent and equitable approach to compensation informed by real-time benchmarking against venture-backed companies and startups in the industry. During your first interview, you can expect an open conversation with your recruiter regarding compensation expectations. Benefits include comprehensive health, dental, vision and life insurance; flexible paid time off; and a retirement savings plan with company match. REQUIREMENTS: - Active Property & Casualty License (required) - 2 or more years of insurance sales experience (Commercial, E&S, Builders Risk, or personal lines home/auto highly preferred) - Familiarity with Salesforce (preferred) - Ability to generate leads and close business - Highly organized and detail-oriented - Propensity and passion for delivering world-class customer service

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