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 Role

Help 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 Do

• Partner directly with existing customers to retain policies and accounts through empathetic communication, education, and expert objection handling
• Confidently navigate rate increases, coverage questions, life changes, and cancellation requests, turning risk into opportunity
• Educate customers on the value of their coverage, available programs, and alternative solutions to prevent unnecessary lapses or cancellations
• Resolve customer requests quickly and accurately through Salesforce cases, inbound calls, and digital channels
• Deliver a top-tier customer experience on every interaction—especially during emotionally charged or time-sensitive situations
• Collaborate with carrier partners, referral sources, and internal teams to ensure the best possible outcomes for customers
• Follow established processes for customer follow-up, documentation, and data integrity
• Contribute to a culture built on motivation, accountability, and continuous improvement
• Take on additional responsibilities as business needs evolve

What You'll Bring

• 4+ years of experience working in the insurance industry, with a strong preference for Property & Casualty and homeowners insurance exposure
• 2+ years in a customer service role, ideally supporting retention, renewals, cancellations, or escalations
• Proven ability to de-escalate difficult conversations, handle objections, and retain customer accounts
• High ownership mentality—you proactively seek answers, leverage resources, and solve problems end-to-end
• Strong time-management skills with the ability to prioritize competing demands in a fast-paced environment
• Comfort operating in ambiguity—you adapt quickly as processes, tools, and customer needs evolve
• Exceptional attention to detail when handling policies, coverage data, and customer documentation
• Ability to work both independently and collaboratively in a fully virtual environment
• Clear, confident verbal and written communication skills that build trust and credibility with customers
• Experience 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 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, Insurtech Amplified Podcast

1. Meet 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.
2. 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 abilities, writing skills, empathy, demeanor, and organization skills. More details will come when you reach this step!
3. Meet the hiring manager
   Next, you'll have a 1 hour video interview with the hiring managers, Chrissy Palmer and Ben Sax, to assess your technical skills for the role.
4. Meet the Team
   Since you'll be joining a close-knit team, we'll ask you to meet other people in the company so we get to know each other a bit better

Moving Forward with Obie

Obie is leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders nationwide. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we’re committed to driving progress for our customers and team. Through advanced digital tools, a trusted agent network, and strategic partnerships, Obie provides real estate investors the insurance coverage they need to move forward confidently.

Obie has you Covered

Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match

Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.

During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.