Customer Service Representative II - Obie Insurance

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 

This is a hands-on service role for experienced, licensed insurance professionals who are comfortable handling property policies and customer requests independently. 

You’ll be part of a structured service team responsible for: 

• Processing endorsements and policy changes 

• Handling billing and renewal questions 

• Communicating clearly with customers and carriers 

• Maintaining accurate documentation in Salesforce 

This role is ideal for someone who: 

• Has solid insurance servicing experience 

• Works well within defined processes 

• Is comfortable managing a steady flow of cases and calls 

• Takes pride in accuracy and responsiveness 

You won’t be managing a book of business or responsible for sales quotas — this is a service-focused role where execution, consistency, and professionalism matter. 

What You'll Do (responsibilities): 

• Resolve customer insurance requests via Salesforce cases, phone calls, and internal workflows 

• Service property policies (coverage changes, renewals, endorsements, billing questions, etc.) 

• Deliver high-quality customer experiences — especially in complex or time-sensitive situations 

• Partner directly with carrier partners and referral sources to advocate for clients 

• Maintain strong documentation and data accuracy within Salesforce 

• Identify inefficiencies and suggest process improvements 

• Operate with accountability and autonomy in a fully remote environment 

What We’re Looking For 

• 4+ years working in the insurance industry (homeowners/property experience strongly preferred) 

• 2+ years in a customer-facing service role 

• Active Property & Casualty insurance license (required before starting — non-negotiable) 

You’ll Stand Out If You Have 

• Experience servicing HO3, DP3, or landlord policies 

• Experience working in an MGA, agency, or carrier environment 

• Strong understanding of endorsements and coverage structure 

• Spanish fluency (preferred but not required) 

What Makes You Successful Here 

• You can prioritize and manage multiple service requests without losing accuracy 

• You understand that details matter — especially in property insurance 

• You’re comfortable making decisions without constant direction 

• You communicate clearly and professionally — even in challenging conversations 

• You’re tech-savvy (Salesforce experience is a plus) 

• You enjoy improving processes instead of just following them 

Why Insurance Professionals Choose Obie 

• Fully remote work environment 

• Opportunity to influence process improvements 

• Exposure to a fast-growing insurtech environment 

• Work with experienced insurance leaders who understand the industry 

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 

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. 

Complete a Project Exercise 
This role requires strong verbal and written communication skills, so we’ll ask you to complete a short exercise. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and organization skills. More details will come when you reach this step! 

Meet the hiring manager 
Next, you'll have a 45-minute video interview with the hiring managers, Ben Sax and Chrissy Palmer, to assess your technical skills for the role. 

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 including 12 week Paid Parental Leave 

• Retirement savings plan with company match 

• Equity participation opportunities 

• Monthly stipends to support a healthy lifestyle and learning and development opportunities 

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.