Customer Service Representative II - Obie Insurance
At Obie, wedon’tjust 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 bethe insuranceexperts, so theydon’thave 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. Ifyou'repassionate about driving change and eager toimpactthe real estate and insurance market, Obie is the place for you.
OurChicago basedemployees arehybrid, andexpected to be in office on Tuesdays and Thursdays.
Brief Summary of Role
This is a hands-on service role for experienced, licensed insurance professionals who are comfortable handling property policies and customer requests independently.
You’llbe part of a structured service team responsible for:
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Processing endorsements and policy changes
- Handling billing and renewal questions
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Communicating clearly with customers and carriers
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Maintainingaccuratedocumentation in Salesforce
This role is ideal for someone who:
- Has solid insurance servicing experience
- 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
Youwon’tbe managing a book of business or responsible for sales quotas — this is a service-focused role where execution, consistency, and professionalism matter.
What You'll Do (responsibilities) :
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Resolve customer insurance requests via Salesforce cases, phone calls, and internal workflows
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Service property policies (coverage changes, renewals, endorsements, billing questions, etc.)
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Deliver high-quality customer experiences — especially in complex or time-sensitive situations
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Partner directly with carrier partners and referral sources to advocate for clients
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Maintain strong documentation and data accuracy within Salesforce
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Identifyinefficiencies and suggest process improvements
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Operate with accountability and autonomy in a fully remote environment
WhatWe’reLooking For
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4+ years working in the insurance industry (homeowners/property experience strongly preferred)
- 2+ years in a customer-facing service role
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Active Property & Casualty insurance license (requiredbefore starting — non-negotiable)
You’llStand Out If You Have
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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 notrequired)
What Makes You Successful Here
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You can prioritize and manage multiple service requests without losing accuracy
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You understand that details matter — especially in property insurance
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You’recomfortable making decisions without constant direction
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You communicate clearly and professionally — even in challenging conversations
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You’retech-savvy (Salesforce experience is a plus)
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You enjoy improving processes instead of just following them
Why Insurance Professionals Choose Obie
- Fully remote work environment
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Opportunity to influence process improvements
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Exposure to a fast-growinginsurtechenvironment
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Work with experienced insurance leaders who understand the industry
Interview Process
At Obie, transparency is core to our interview process. We focus on open communication and a positiveexperience; no trickquestions—just honest conversations aboutyourskills and aspirations. To help you prepare, please familiarize yourself with these resources before moving forward:
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Our company’s blogtolearn 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 a