Insurance Customer Service Representative II Chicago, IL​/Remote

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.

While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, PA, SC, SD, TN, TX, UT, WI

Obie is looking for an innovative, bright, motivated and hard-working individual to join our team to help us accomplish our mission of combining insurance know-how, innovative technology and world-class service to delight our customers.

Those successful in this role have a strong sense of intellectual curiosity, the ability to think critically, and a desire to help others solve problems. Additionally, you'll be self motivated and directed with a strong ability to work autonomously as you'll be expected to succeed without heavy direction.

The hours for this role will fall within 10:00 AM - 8:00 PM EST, Monday - Friday. It is an 8-1/2 work day with 30 minutes for lunch.

• Resolve insurance requests quickly and accurately for our current clients through Salesforce cases, incoming phone calls, and other sources of customer requests
• Deliver top tier customer experience with every interaction
• Work closely with current customers to educate them on the benefits of our programs and products while ensuring all accounts are serviced in a timely manner
• Work closely with referral sources and carrier contacts to successfully deliver for our customers
• Adhere to our processes related to customer follow-up and data gathering
• Maintain the existing culture predicated on motivation and positive reinforcement while upholding a standard of accountability to self, team, and company
• Complete other duties as assigned

• 4+ years working in insurance, homeowner experience is preferred
• 2+ years in a customer service role
• Fearlessness and adaptability in a fast-moving, ever changing environment and a strong ability to multi-task
• Detail orientation in everything you do: there is a lot of customer and policy information flying by you – having a keen eye here is essential to your success
• Ability to demonstrate how to prioritize competing demands while managing your time effectively
• As the role is remote, the ability to collaborate in a virtual environment is a must
• Excellent verbal and written communication skills to assist with customer needs, problem solve, answer questions, and leave a positive impression.
• Strong sense of ownership and resourcefulness : comfortable working independently, using available tools, documentation, and subject-matter experts to solve problems efficiently.
• Experience and comfort using a variety of software tools from Salesforce, Excel and G Suite , to include but not limited to policy management and accounting systems
• Personal standard for excellence:
  strong process orientation and interest in finding better ways to do things
• Positive “can do” attitude and a desire to contribute to a growing, energetic work environment
• An active Property & Casualty insurance license is required before starting.

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 Linked In to see…