Customer Success 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. 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 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. Meet the hiring manager
   Next, you'll have a 45-minute video interview with the hiring manager to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong planning, collaboration, and leadership 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 how well you apply key project management strategies. More details will come when you reach this step!
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:

• Competitive salary
• Flexible time off with an encouraged minimum time away to support a healthy work-life balance
• 12 weeks of Paid Parental Leave
• Great health, dental and vision coverage
• Life Insurance
• Flexible Spending & Health Savings Accounts
• Stock Options
• 401k match
• Pet Insurance Reimbursement
• Health and wellness benefit
• Equipment budget - everything you need to do your best work
• Professional development support
• Summer hours

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.