Obie · 1 month ago
P & C Licensed Insurance Customer Service Representative II
United States
Full-time
Remote
Mid Level
4+ years expObie is a company focused on providing insurance solutions for real estate investors and landlords. They are seeking an experienced insurance professional to help customers retain their insurance policies and navigate challenging situations with empathy and expertise.
Commercial InsuranceCommercial Real EstateInsuranceInsurTechReal Estate
Responsibilities
Partner directly with existing customers to retain policies and accounts through empathetic communication, education, and expert objection handling
Confidently navigate rate increases, coverage questions, life changes, and cancellation requests, turning risk into opportunity
Educate customers on the value of their coverage, available programs, and alternative solutions to prevent unnecessary lapses or cancellations
Resolve customer requests quickly and accurately through Salesforce cases, inbound calls, and digital channels
Deliver a top-tier customer experience on every interaction—especially during emotionally charged or time-sensitive situations
Collaborate with carrier partners, referral sources, and internal teams to ensure the best possible outcomes for customers
Follow established processes for customer follow-up, documentation, and data integrity
Contribute to a culture built on motivation, accountability, and continuous improvement
Take on additional responsibilities as business needs evolve
Qualification
Required
4+ years of experience working in the insurance industry, with a strong preference for Property & Casualty and homeowners insurance exposure
2+ years in a customer service role, ideally supporting retention, renewals, cancellations, or escalations
Proven ability to de-escalate difficult conversations, handle objections, and retain customer accounts
High ownership mentality—you proactively seek answers, leverage resources, and solve problems end-to-end
Strong time-management skills with the ability to prioritize competing demands in a fast-paced environment
Comfort operating in ambiguity—you adapt quickly as processes, tools, and customer needs evolve
Exceptional attention to detail when handling policies, coverage data, and customer documentation
Ability to work both independently and collaboratively in a fully virtual environment
Clear, confident verbal and written communication skills that build trust and credibility with customers
Experience using Salesforce, CRM platforms, Excel, and Google Workspace (or similar systems)
Personal standard for excellence: strong process orientation and interest in finding better ways to do things
An active Property & Casualty insurance license is required before starting
Benefits
Comprehensive health, dental, vision and life insurance
Flexible paid time off
Retirement savings plan with company match
Company
Obie
Obie is an insurance company that specializes in rental property and landlord insurance services.
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$39MKey Investors
Battery VenturesY Combinator
2026-01-13Acquired
2023-05-17Series B· $25.5M
2021-05-26Series A· $10.7M
Leadership Team
Ryan Letzeiser
Co-Founder & CEO (Y Combinator S19)
Aaron Letzeiser
Co-Founder
Recent News
2025-12-13
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2025-04-02
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2025-01-22
Company data provided by crunchbase