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 RoleHelp customers stay protected when it matters most. We’re looking for an experienced insurance professional who thrives in high-stakes conversations, knows how to calm challenging situations, and can confidently guide customers to the right decision—even when cancellation is on the table.This role is ideal for someone with a strong background in customer advocacy, policy retention, and objection handling who wants to make a real impact on both customer outcomes and business results.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. They are self motivated 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 DoPartner directly with existing customers to retain policies and accounts through empathetic communication, education, and expert objection handlingConfidently navigate rate increases, coverage questions, life changes, and cancellation requests, turning risk into opportunityEducate customers on the value of their coverage, available programs, and alternative solutions to prevent unnecessary lapses or cancellationsResolve customer requests quickly and accurately through Salesforce cases, inbound calls, and digital channelsDeliver a top-tier customer experience on every interaction—especially during emotionally charged or time-sensitive situationsCollaborate with carrier partners, referral sources, and internal teams to ensure the best possible outcomes for customersFollow established processes for customer follow-up, documentation, and data integrityContribute to a culture built on motivation, accountability, and continuous improvementTake on additional responsibilities as business needs evolveWhat You'll Bring4+ years of experience working in the insurance industry, with a strong preference for Property & Casualty and homeowners insurance exposure2+ years in a customer service role, ideally supporting retention, renewals, cancellations, or escalationsProven ability to de-escalate difficult conversations, handle objections, and retain customer accountsHigh ownership mentality—you proactively seek answers, leverage resources, and solve problems end-to-endStrong time-management skills with the ability to prioritize competing demands in a fast-paced environmentComfort operating in ambiguity—you adapt quickly as processes, tools, and customer needs evolveExceptional attention to detail when handling policies, coverage data, and customer documentationAbility to work both independently and collaboratively in a fully virtual environmentClear, confident verbal and written communication skills that build trust and credibility with customersExperience using Salesforce, CRM platforms, Excel, and Google Workspace (or similar systems)Personal standard for excellence: strong process orientation and interest in finding better ways to do things.An active Property & Casualty insurance license is required before starting.Interview ProcessAt 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, Insurtech Amplified PodcastMeet us and get to know Obie You'll first talk to Mary on a 30-minute call to determine whether we’re a good fit for one another. You’ll learn more about Obie and have the chance to ask about our company, team, culture, and product.Complete a Project Exercise This role requires strong communication and analytical skills, so we’ll ask you to complete a short exercise. You can take your time and use the resources available. We’ll assess your problem-solving abilit