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Role Description
This is a hands-on service role for experienced, licensed insurance professionals who are comfortable handling property policies and customer requests independently. You’ll be part of a structured service team responsible for:
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Processing endorsements and policy changes
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Handling billing and renewal questions
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Communicating clearly with customers and carriers
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Maintaining accurate documentation in Salesforce
This role is ideal for someone who:
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Has solid insurance servicing experience
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Works well within defined processes
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Is comfortable managing a steady flow of cases and calls
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Takes pride in accuracy and responsiveness
You won’t be managing a book of business or responsible for sales quotas — this is a service-focused role where execution, consistency, and professionalism matter.
Qualifications
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4+ years working in the insurance industry (homeowners/property experience strongly preferred)
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2+ years in a customer-facing service role
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Active Property & Casualty insurance license (required before starting — non-negotiable)
Requirements
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Experience servicing HO3, DP3, or landlord policies
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Experience working in an MGA, agency, or carrier environment
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Strong understanding of endorsements and coverage structure
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Spanish fluency (preferred but not required)
Benefits
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Comprehensive health, dental, vision and life insurance
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Flexible paid time off including 12 week Paid Parental Leave
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Retirement savings plan with company match
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Equity participation opportunities
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Monthly stipends to support a healthy lifestyle and learning and development opportunities
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:
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Our company’s blog to learn more about the market we serve and the information our customers value.
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Check out our LinkedIn to see how people interact with our brand and product.
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Press and podcast features like Inc. 5000, TechCrunch, Innovate State, Uncontested Investing Podcast, Insurtech Amplified Podcast.
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.
Complete a Project Exercise: This role requires strong verbal and written communication skills, so we’ll ask you to complete a short exercise. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and organization skills. More details will come when you reach this step!
Meet the hiring manager: Next, you'll have a 45-minute video interview with the hiring managers, Ben Sax and Chrissy Palmer, to assess your technical skills for the role.
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.
Company Description
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.
