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Customer Service Team Lead - Life & Health

Brown & Brown · IL · Remote available · Full time

Posted Oct 5, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you trained or coached someone new on a team.

What they are checking: Experience supporting onboarding through shadowing and refresher sessions.

How do you stay friendly with teammates while still holding them to service standards?

What they are checking: The balance a team lead needs between peer and accountability roles.

Tell me about a process improvement you suggested and how it worked out.

What they are checking: Initiative and continuous improvement mindset the posting emphasizes.

What does excellent member service look like on a life and health call?

What they are checking: A clear personal standard for service that they can model for others.

What would you do

A CSR comes to you mid-call confused about a member's life policy. How do you help in the moment?

What they are checking: Quick, calm coaching as the first escalation point without taking over the call.

How would you give feedback to a CSR whose call quality scores are slipping?

What they are checking: Constructive feedback that is specific and helps the person improve.

How would you handle an angry member who asks for a supervisor and you are the first escalation?

What they are checking: De-escalation and problem solving that resolves issues before they go higher.

How would you handle it if a CSR kept asking you questions they should know by now?

What they are checking: Patience balanced with building independence in the team.

About the work

What compliance rules matter most when CSRs talk with members about life and health insurance?

What they are checking: Awareness of privacy and accuracy rules that protect members and the company.

How would you spot workflow problems in the team's daily operations?

What they are checking: Using queue data and patterns to find bottlenecks, part of workflow oversight.

Practice this interview out loud.

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The full job description

As published by Brown & Brown.

Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers. One80 Intermediaries is seeking a Customer Service Team Lead – Life & Health to join our growing team. The Customer Service Team Lead at Pearl Insurance supports the daily operations of the Affinity Customer Service team by providing frontline coaching, technical guidance, and workflow oversight, ensuring consistent execution of service standards and operational excellence. The Team Lead serves as a first‑level escalation point for Customer Service Representatives (CSRs), assists with training and quality activities, and reinforces departmental expectations for service excellence, accuracy, and compliance. Working under the general direction of the Customer Service Supervisor or Manager, the Team Lead promotes operational consistency, supports employee development, and helps maintain a positive, member‑focused environment. This role is expected to model organizational values, demonstrate accountability, and contribute to a culture of continuous learning, teamwork, and high‑quality service. How You Will Contribute: • Serve as the initial escalation resource for CSRs for procedures, systems, product knowledge, and member inquiries. • Support new hire onboarding and ongoing training through shadowing, refresher sessions, job aids, and side‑by‑side coaching. • Assist the Supervisor with monitoring queue activity, service levels, and workflow distribution. • Conduct call observations and participate in quality assurance (QA) reviews; document and elevate coaching insights. • Provide real‑time support using the Five9 and Synergy. • Review survey comments and member feedback, identifying trends for process or training improvements. • Reinforce departmental procedures, customer service standards, and HIPAA requirements. • Partner with Workforce Management to identify coverage needs, schedule adherence issues, and call‑volume trends. • Assist in developing and maintaining SOPs, training materials, workflows, and reference documentation. • Promote team engagement through effective communication, professionalism, peer support, and recognition. • Demonstrate dependable and punctual attendance to ensure consistent frontline support. Leadership Responsibilities: • Offering timely performance insights and development observations to the Supervisor. • Supporting consistent execution of departmental expectations, procedures, and service behaviors. • Modeling organizational core values, professionalism, accountability, and ownership of outcomes. • Contributing to a collaborative, inclusive, and continuous‑improvement‑focused culture. Skills & Experience to be Successful: • High school diploma required, associate or bachelor’s degree preferred. • Minimum of 3 years of customer service experience, preferably in the insurance industry. • Previous senior CSR, mentor, or informal leadership experience. • Technical experience with Five9 telephony platform. • Life & Health insurance licenses may be required for this role. About One80: One80 Intermediaries is part of Arrowhead Intermediaries, a global insurance distribution platform that offers deep specialization, scale, and innovation across wholesale brokerage, program administration, and specialty insurance. With more than 7,000 professionals worldwide and a collective portfolio exceeding $18 billion in premium placed in 2024, our combined organization delivers a diverse trading platform for insurance carriers as well as expanded access and niche solutions for brokers and customers navigating complex and hard-to-place risks. The platform combines entrepreneurial culture with operational excellence to deliver tailored solutions and long-term value across the insurance ecosystem. Pay Range 21.00 - 21.00 Hourly The pay range provided above is made in good faith and based on our lowest and highest annual salary or hourly rate paid for the role and takes into account years of experience required, geography, and/or budget for the role. Teammate Benefits & Total Well-Being We go beyond standard benefits, focusing on the total well-being of our teammates, including: • Health Benefits : Medical/Rx, Dental, Vision, Life Insurance, Disability Insurance • Financial Benefits : ESPP; 401k; Student Loan Assistance; Tuition Reimbursement • Mental Health & Wellness : Free Mental Health & Enhanced Advocacy Services • Beyond Benefits : Paid Time Off, Holidays, Preferred Partner Discounts and more. Not reflective of all benefits. Enrollment waiting periods or eligibility criteria may apply to certain benefits. Benefit details and offerings may vary for subsidiary entities or in specific geographic locations. Recruiting Vendor Disclosure Statement Brown & Brown does not accept unsolicited resumes from external recruiters, recruitment vendors or employment agencies ("Recruiting Vendors"). Recruiting Vendors must have a valid written agreement and received prior written authorization from an authorized Brown & Brown representative before submitting candidates for any publicly posted role. Any unsolicited resumes submitted to Brown & Brown or its employees become the property of Brown & Brown, and no fees will be paid for such submissions. Additional information regarding this policy can be found on our careers page. The Power To Be Yourself As an Equal Opportunity Employer, we are committed to fostering an inclusive environment comprised of people from all backgrounds, with a variety of experiences and perspectives, guided by our Diversity, Inclusion & Belonging (DIB) motto, “The Power to Be Yourself”.

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