Job Overview
Location
Remote
Job Type
Full-time
Category
Sales Manager
Date Posted
February 22, 2026
Full Job Description
đź“‹ Description
- • **Lead a High-Performing Insurance Sales Team:** Jerry.ai is seeking a dynamic and results-driven Team Lead for our Insurance Sales department. This is a unique opportunity to join a rapidly growing, pre-IPO startup that is revolutionizing the car ownership experience through its AI-powered super app. You will be instrumental in scaling our sales operations, reporting directly to the Director of Contact Center Operations. Your primary focus will be to serve as a player-coach, guiding a team of talented Insurance Sales Agents to achieve and exceed ambitious performance targets.
- • **Drive Excellence in Sales Performance and Customer Experience:** As a Team Lead, you will be the linchpin between our operational strategy and front-line execution. You will cultivate a culture of excellence by meticulously conducting call audits, rigorously tracking key performance indicators (KPIs), and providing consistent, constructive monthly coaching sessions focused on talent development and performance enhancement. Your leadership will directly impact our ability to provide a tailored, seamless, and exceptional experience for our 5 million customers, simplifying the often complex and expensive aspects of car ownership.
- • **Champion Operational Improvements and Product Innovation:** You will play a critical role in enhancing our internal processes and the Jerry app itself. By providing direct, actionable feedback to our Product Managers and Engineering teams, you will contribute to the refinement of our Standard Operating Procedures (SOPs), the optimization of our Generative AI (GenAI) tools, and the overall improvement of the Jerry app experience. Your insights from the front lines will be invaluable in shaping the future of our super app.
- • **Engage Directly with Customers and Lead by Example:** To stay sharp on the customer experience and to effectively coach your team, you will actively participate in direct customer engagement. This includes hopping on the front lines to assist customers, simplifying complex insurance jargon, preparing quotes, and binding policies. By leading through example, you will demonstrate best practices in customer interaction and reinforce our commitment to a customer-first approach.
- • **Contribute to Strategic Growth and Market Disruption:** Collaborate closely with the broader insurance operations team to identify opportunities for growth. This involves pinpointing gaps in customer coverage and developing strategies to increase new business policy sales and enhance customer retention. You will be a key player in our mission to disrupt the massive car ownership market and scale Jerry.ai into a $10 billion business.
- • **Foster a Talent-Dense and Growth-Oriented Environment:** Join a team comprised of high-caliber professionals from leading companies such as McKinsey, Amazon, BCG, and Nvidia. Jerry.ai offers an environment that prioritizes first-principles thinking, encourages rapid career acceleration, and provides unparalleled opportunities for professional development. You will be immersed in a culture that values curiosity, collaboration, and a passion for solving real-world problems.
- • **Manage Team Operations and Onboarding:** Oversee the daily operations of your assigned sales squad. This includes managing schedules, conducting performance reviews, and ensuring a smooth and effective onboarding process for new, high-caliber hires. Your ability to attract, develop, and retain top talent will be crucial to our success.
- • **Embrace a Player-Coach Mentality:** This role is designed for individuals who are energized by both strategic leadership and hands-on execution. You will be expected to manage your team's performance while also being ready to step in and contribute directly to sales activities, ensuring the team consistently meets its objectives. Your adaptability and willingness to engage at all levels will be key.
- • **Leverage Data to Drive Performance:** Utilize data analytics to understand team performance, identify trends, and implement data-driven strategies for improvement. You will be responsible for setting clear expectations and holding your team accountable to achieving key performance indicators (KPIs) related to sales volume, conversion rates, customer satisfaction, and policy retention.
- • **Innovate and Adapt in a Fast-Paced Startup:** Thrive in the dynamic and often ambiguous environment of a fast-growing startup. You will be comfortable navigating change, adapting quickly to new initiatives, and contributing to the continuous evolution of our sales processes and customer engagement strategies. Your proactive approach to problem-solving will be highly valued.
- • **Simplify Complex Insurance for Millions:** At Jerry.ai, we are not just selling insurance; we are simplifying one of the most significant and often frustrating aspects of car ownership. As a Team Lead, you will embody this mission, empowering your team to provide clear, concise, and valuable solutions to our customers, building trust and loyalty with every interaction.
- • **Contribute to a $2 Trillion Market Opportunity:** Be part of a company that is tackling a massive market opportunity. With significant funding, impressive revenue growth, and a clear vision for the future, Jerry.ai is poised for substantial expansion. Your contributions will directly fuel this growth and help us achieve our ambitious goals.
- • **Build the Future of the Jerry Super App:** Your feedback and insights will directly influence the development of the Jerry super app, ensuring it remains the most comprehensive and user-friendly platform for car owners. You will be a key stakeholder in shaping the technology and services that define the future of car ownership management.
🎯 Requirements
- • Minimum 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 (e.g., Team Lead, Senior Representative, or Manager).
- • Active Property & Casualty (P&C) license required, or a strong willingness and ability to obtain one quickly.
- • Strong technical aptitude, with comfort and proficiency in CRM tools and omni-channel communication platforms.
🏖️ Benefits
- • Competitive compensation package including base salary and commission ($100,000 - $150,000 per year).
- • Comprehensive health, vision, and dental insurance.
- • Generous paid time off (PTO) and paid parental leave.
- • 401(k) plan with employer matching.
Skills & Technologies
Senior
Remote
About Jerry Technologies, Inc.
Jerry is a technology company focused on simplifying and personalizing the car ownership experience. They offer a mobile app that acts as a digital assistant for car owners, providing services such as insurance comparison and purchasing, maintenance scheduling, roadside assistance, and parking assistance. Jerry aims to reduce the stress and cost associated with owning a vehicle by leveraging AI and data analytics to offer tailored solutions and competitive pricing. Their platform connects users with a network of service providers and insurance carriers, streamlining the entire car ownership lifecycle.
