Customer Service Representative II

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.

What You'll Do

• 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

What You'll Bring

• 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

You'll Stand Out If You Have

• 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)

What Makes You Successful Here

• 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

Why Insurance Professionals Choose Obie

• 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

We are scaling quickly and looking to add multiple experienced professionals to the team. If you are licensed, experienced, and ready to contribute at a higher level — we want to meet you.

Click here for some insight into our culture!

The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.