Customer Support Team Lead, Insurance

You could lead a team anywhere. Why us?

• Join a pre-IPO startup with capital, traction, and runway ($240M funded | 60X revenue growth in 5 years | $2T market size).

• Work with a high-caliber team from companies like Lemonade, GEICO, Bain & Co, and McKinsey.

• Disrupt a massive market and help us scale to a $10B business in the next few years.

• Be immersed in a talent-dense environment that prioritizes first-principles thinking and rapid career acceleration.

About the Opportunity:

Jerry is growing fast, and more than 5 million customers count on us to make car insurance simple. As Team Lead on our Insurance Service team , you’ll work closely with the Manager, Contact Center Operations, to coach a team of 10 insurance agents and make sure every customer gets a white-glove experience.

Behind every great customer experience at Jerry is a team of licensed agents, ready on calls, chats, and digital channels. As their leader, you’ll raise that team’s game: coaching every agent to their best, setting a high bar for service, keeping the team compliant, and solving problems before customers ever notice them.

How You Will Make an Impact:

• Coaching & Performance: Lift team results through regular 1:1s, clear feedback, and performance reviews, and catch performance issues early.

• Operations & Compliance: Own staffing and coverage, quality reviews, timesheets, and PTO, and keep every agent compliant with insurance regulations and Jerry policy.

• Escalations: Resolve complex product, carrier, and system issues, and step in on customer calls when needed.

• Cross-Functional Impact: Work across the business to fix operational problems at the source and help shape the initiatives that scale Jerry’s customer experience.

Who You Are:

• A People Leader: You drive results by coaching consistently, not just when something goes wrong.

• An Insurance & Systems Expert: You know policies, regulations, and call center and CRM tools well enough to answer tough questions and troubleshoot complex issues.

• Customer-Obsessed: You hold a high bar for service, sweat the details, and fix issues fast.

• Truth-Seeking: You bring rigor to every part of the job, from your own work to your team’s. Resolving a customer’s issue is just the start; you aim to leave an impression that keeps them coming back.

Compensation & Benefits:

• Pay : $50,000 - $60,000 annual base

• Workplace : Remote (we will provide you with equipment)

• Benefits : Insurance (health, vision, dental), paid time off, paid parental leave, 401K with employer matching, etc.

Minimum Requirements:

• 3+ years of experience in a high-volume contact center in the insurance or financial services industry.

• Demonstrated experience in a leadership or "player-coach" capacity (Team Lead, Senior Rep, or Manager).

• Active Property & Casualty (P&C) license is required (or willingness to obtain one quickly).

• Strong technical aptitude and comfort with CRM tools and omni-channel communication platforms.

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at View email address on aiapply.co

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

About Jerry.ai

Jerry is building the first AI-powered advisor to manage all your physical assets.

Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.

We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.

Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.

We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.