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The Baldwin Group

via Workday

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Customer Service Representative II

Anywhere
Full-time
Posted 1/23/2026
Direct Apply
Key Skills:
Customer Support
SQL
Troubleshooting

Compensation

Salary Range

$70K - 120K a year

Responsibilities

Assist customers with insurance requests, educate clients, and manage policy information efficiently.

Requirements

Requires 4+ years in insurance, customer service experience, and an active property & casualty license; your experience aligns partially but lacks specific insurance licensing and direct insurance industry experience.

Full 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. 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 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 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. What You'll Do 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 a 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 What You'll Bring 4+ years working in insurance, homeowners 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. 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. The Baldwin Group (previously Baldwin Risk Partners) is a cohesive group of experts in business insurance, employee benefits, retirement planning, and all areas of private and personal insurance. Since 2011, we’ve evolved from a local business into a national firm with a vast network of specializations serving two million clients across the country. At The Baldwin Group, we provide solutions so our clients can pursue what’s possible for themselves, their families, and their businesses. Whether renting a first apartment, opening a small business or taking a company public, we offer solutions to support clients at every step of their journey giving them peace of mind to pursue their purpose, passion, and dreams. We Protect the Possible. The Baldwin Group is an equal employment opportunity firm and strives to comply with all laws prohibiting discrimination based on race, color, religion, age, sex (including sexual orientation and gender identity), national origin or ancestry, disability, military status, marital status, and any other category protected by federal, state, or local laws. All such discrimination is unlawful, and all persons involved in the operations of the firm are prohibited from engaging in this conduct.

This job posting was last updated on 1/24/2026

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