Customer Service Representative II - Obie Insurance

📋 Description

• • 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.
• • 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
• • Identifying inefficiencies and suggesting process improvements
• • Operating with accountability and autonomy in a fully remote environment
• • 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.
• • 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
• • We’re looking 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, and is tech-savvy (Salesforce experience is a plus).
• • You’ll stand out if you have experience servicing HO3, DP3, or landlord policies, experience working in an MGA, agency, or carrier environment, a strong understanding of endorsements and coverage structure, and Spanish fluency (preferred but not required).
• • You can prioritize and manage multiple service requests without losing accuracy
• • You understand that details matter — especially in property insurance
• • You’re comfortable making decisions without constant direction
• • You communicate clearly and professionally — even in challenging conversations
• • You’re tech-savvy (Salesforce experience is a plus)
• • You enjoy improving processes instead of just following them
• • 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.
• • Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:
• • Comprehensive health, dental, vision and life insurance
• • Flexible paid time off including 12 week Paid Parental Leave
• • Retirement savings plan with company match
• • Equity participation opportunities
• • Monthly stipends to support a healthy lifestyle and learning and development opportunities
• • Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry.