Customer Service Representative II
About The Position
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 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: Processing endorsements and policy changes Handling billing and renewal questions Communicating clearly with customers and carriers Maintaining accurate documentation in Salesforce This role is ideal for someone who: Has solid insurance servicing experience Works well within defined processes Is comfortable managing a steady flow of cases and calls 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.
Requirements
- 4+ years working in the insurance industry (homeowners/property experience strongly preferred)
- 2+ years in a customer-facing service role
- Active Property & Casualty insurance license (required before starting — non-negotiable
Nice To Haves
- Experience servicing HO3, DP3, or landlord policies
- Experience working in an MGA, agency, or carrier environment
- Strong understanding of endorsements and coverage structure
- Spanish fluency (preferred but not required)
Responsibilities
- Resolve customer insurance requests via Salesforce cases, phone calls, and internal workflows
- Service property policies (coverage changes, renewals, endorsements, billing questions, etc.)
- Deliver high-quality customer experiences — especially in complex or time-sensitive situations
- Partner directly with carrier partners and referral sources to advocate for clients
- Maintain strong documentation and data accuracy within Salesforce
- Identify inefficiencies and suggest process improvements
- Operate with accountability and autonomy in a fully remote environment
Benefits
- Fully remote work environment
- Opportunity to influence process improvements
- Exposure to a fast-growing insurtech environment
- Work with experienced insurance leaders who understand the industry
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
Number of Employees
101-250 employees
