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, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NY, NC, OH, OR, PA, SC, SD, TN, TX, UT, WI

Brief Summary of Role

As the Service Lead - Billing you will play a key role in managing a team of Virtual Assistants (VAs) responsible for billing operations. Your mission will be to establish a seamless operational structure, improve team engagement, and optimize performance management to ensure timely, accurate, and efficient service delivery in relation to billing functions.

You will report directly to the Head of Insurance Services and work closely with cross-functional teams to enhance our billing processes, ensure compliance, and deliver exceptional service.

What you'll Do

• Lead and coach a team of Virtual Assistants, providing clear direction and regular feedback
• Conduct regular 1:1 meetings and team huddles to foster engagement and accountability
• Drive engagement by addressing team needs, resolving friction points, and promoting collaboration
• Develop, maintain, and update Standard Operating Procedures (SOPs) in collaboration with the Service VA Lead
• Manage team schedules, time-off requests, and resource allocation to meet service level agreements (SLAs)
• Oversee distribution of cases, monitor team productivity, and address operational challenges proactively
• Analyze trends in productivity and quality, creating strategies for continuous improvement
• Document coaching notes and other administrative duties as required
• Handle customer escalations and complaints with professionalism and urgency

What you'll Bring

• 2+ years of service/sales management experience in a P&C call center or start-up environment, effectively managing a team of 6 or more customer facing associates, preferably in billing units
• Active P&C license required
• Commercial lines experience with a proven track record of excellent customer interaction
• Experience at an MGA/MGU/Program Administrator and/or insurtech is preferred
• Proven track record utilizing Salesforce to measure and drive individual and team KPIs, with a focus on optimizing performance and enhancing customer service
• Excellent communication and presentation skills, both verbal and written, to effectively convey strategies and drive results
• Analytical and problem-solving skills with the ability to identify billing opportunities for improving customer experiences, quality of work and productivity
• Team-oriented mindset with the flexibility to adapt to evolving business strategies and priorities, fostering a collaborative and supportive work environment
• Ability to work independently, prioritize tasks, and manage multiple projects simultaneously in a fast-paced environment, ensuring timely delivery of results

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, Dana Markel, to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong insurance service leadership and management experience, so you’ll be presented with a short exercise to complete to provide you a chance to flex those muscles. You will be able to complete this exercise on your own time, so please be thorough and use the resources available to you. More on this when you get there!
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.