About the Role
Service Lead – Billing
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