Supervisor, Insurance Sales

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 McKinsey, Amazon, BCG, and Nvidia.

• 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:

We are looking for a Supervisor, Insurance Sales who is energized by the challenge of scaling a high-performance sales organization. Reporting to the Director, Contact Center Operations, you will be a player-coach responsible for the success of a team of Insurance Sales Agents.

At Jerry, we don’t just sell insurance; we simplify the most complex and expensive aspects of car ownership. As a Team Lead, you will ensure your team provides a tailored, seamless experience for our 5M+ customers. You will be the bridge between front-line execution and operational strategy, coaching your team to hit aggressive targets while partnering with Product and Engineering to build the future of the Jerry super app.

How You Will Make an Impact:

• Performance Coaching: Build a culture of excellence by conducting call audits, tracking key metrics, and providing rigorous monthly coaching for talent development.

• Team Leadership: Manage the daily operations of your squad, including scheduling, performance reviews, and onboarding new high-caliber hires.

• Operational Excellence: Provide direct feedback to Product Managers and Engineering to enhance our internal SOPs, GenAI tools, and the Jerry app experience.

• Direct Customer Engagement: Lead by example by hopping on the front lines, simplifying jargon, preparing quotes, and binding policies to stay sharp on the customer experience.

• Growth Strategy: Collaborate across insurance operations to identify gaps in coverage and find ways to increase new business policy sales and customer retention.

Who You Are:

• A Proven Leader: You have experience coaching, mentoring, or leading sales teams in a high-velocity environment.

• A "First Principles" Thinker: You don't just follow a script; you understand the "why" and can identify gaps to build better processes.

• Results-Oriented: You live for the metrics. You enjoy the challenge of hitting KPIs and holding your team accountable to a high bar of performance.

• An Expert Communicator: You can explain complex insurance concepts with ease and maintain a professional, empathetic attitude under pressure.

• Adaptable: You thrive in the ambiguity of a fast-growing startup and are comfortable moving between high-level strategy and hands-on execution.

• Customer-obsessed: You genuinely care about making the purchasing process less painful for customers and champion a customer-first culture where every interaction builds trust.

Compensation & Benefits:

• Pay: $100,000 - $150,000+ with commission per year

• 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 personal lines insurance sales or a high-volume contact center environment.

• 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, only applicants under consideration will be contacted.

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 [email protected]

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.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. 

Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.

We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. 

Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.

Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.