Customer Success Representative II
ObieAbout the role
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. The working hours for this role would be 11:30-8:00 PM EST or 10:30-7:00 PM EST.
While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, OR, PA, SC, SD, TN, TX, UT, WI
Brief Summary of Role:
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 the ability to critically think, have a strong intellectual curiosity and a desire to help others solve problems. Additionally, you’ll be self motivated and directed. An ability to work autonomously and collaborate in a virtual environment is a must. You will be expected to succeed without heavy direction.
What you'll Do
- Resolve insurance requests quickly and accurately for our current clients
- 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 appropriately
- Work closely with referral sources and carrier contacts to successfully deliver for our customers
- Crush individual, team and department goals
- 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
What you'll Bring
- 2+ years working in insurance customer service
- Fearlessness and adaptability in a fast-moving, ever changing environment and ability to work on multiple tasks at onceDetail orientation in everything you do: there is a lot of customer and policy information flying by you – having a keen eye here is essential
- Prior experience and the ability to demonstrate how to prioritize competing demands while managing your time effectively
- Excellent verbal and written communication skills to assist with customer needs, problem solve, answer questions, and leave a positive impression
- 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.
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
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