Customer Service Representative II - Obie Insurance

Resonance CX Partners' mission is to help experienced professionals find opportunities that truly align with their values. We are not a staffing firm or agency. Resonance CX does not hire for these positions—we identify and validate them from customer-focused organizations directly.

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.

About the 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, and 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.

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

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)

Qualifications

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)

Skills

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

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

Interview Process

At Obie, transparency is core to our interview process. We focus on open communication and a positive experience; no trick questions—just honest conversations about your skills and aspirations. To help you prepare, please familiarize yourself with these resources before moving forward:

• Our company's blog to learn more about the market we serve and the information our customers value.
• Check out our LinkedIn to see how people interact with our brand and product.
• Press and podcast features like Inc. 5000, TechCrunch, Innovate State, Uncontested Investing Podcast, Insur #ResonanceCXPartners.