Sr. Service Lead - CSR's

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

We are seeking a proactive and results-driven Sr. Service Lead to oversee performance management within our customer service team specializing in landlord insurance. The ideal candidate will bring a strong background in leadership, insurance operations, and data analysis to inspire a high-performing, collaborative team while ensuring efficient operations and exceptional customer experiences.

What you'll Do

• Monitor, analyze, and report team performance metrics to identify trends and areas for improvement
• Implement strategies to optimize productivity, quality, and customer satisfaction
• Provide regular quality monitoring audits, coaching, feedback, and development opportunities to team members
• Conduct team meetings, 1:1 sessions, and training initiatives to drive performance that aligns with company goals
• Track attendance, time-off requests, and adherence to schedules to ensure proper staffing levels
• Co-manage workflow priorities and resolve operational bottlenecks with leadership peers
• Utilize performance data and customer feedback to drive continuous improvement
• Handle customer escalations and complaints with professionalism and urgency
• Create and maintain a collaborative, motivating, and inclusive environment

What you'll Bring

• Experience: 5+ years of leadership experience in customer service, with at least 2 years in the insurance industry. Effectively managing a team of 5 or more customer facing associates.
• Insurance Expertise: Knowledge of landlord insurance, with P&C insurance is preferred. Experience at an MGA/MGU/Program Administrator and/or insurtech is preferred. P&C license required.
• Analytical Skills: Ability to analyze data, interpret performance trends, and develop actionable strategies.
• Leadership Abilities: Proven track record of fostering collaboration, driving motivation, and managing performance. Prior co-managing experience is preferred. Team-oriented mindset with the flexibility to adapt to evolving business strategies and priorities.
• Organizational Skills: Strong capability to track attendance, manage schedules, and prioritize tasks effectively. Ability to work independently, prioritize tasks, and manage multiple projects simultaneously in a fast-paced environment, ensuring timely delivery of results.
• Communication Skills: Excellent verbal and written communication skills for engaging with team members and leadership.
• System Knowledge: Proven track record utilizing Salesforce to measure and drive individual and team KPIs, with a focus on optimizing performance and enhancing customer service

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