Job Overview
Location
Remote
Job Type
Full-time
Category
Sales Manager
Date Posted
February 22, 2026
Full Job Description
đź“‹ Description
- • **Lead and Inspire a High-Performance Sales Team:** As a Supervisor, Insurance Sales at Jerry.ai, you will be at the forefront of scaling our rapidly growing sales organization. You will serve as a player-coach, directly responsible for the success and development of a dedicated team of Insurance Sales Agents. Your primary mission is to foster a culture of excellence, drive aggressive sales targets, and ensure every customer interaction is a positive and seamless experience.
- • **Drive Sales Performance and Customer Satisfaction:** You will meticulously track key performance indicators (KPIs), conduct regular call audits, and provide rigorous, constructive coaching to your team members. This hands-on approach to performance management will not only help individuals grow but also ensure the team consistently meets and exceeds its sales objectives. Your leadership will be instrumental in simplifying the complex and often stressful process of purchasing car insurance for our 5 million customers.
- • **Champion Operational Excellence and Product Enhancement:** You are more than just a manager; you are a vital link between front-line execution and strategic development. You will gather invaluable insights from your team's daily interactions and customer feedback, translating these into actionable recommendations for our Product Managers and Engineering teams. Your input will directly influence the enhancement of our internal Standard Operating Procedures (SOPs), the refinement of our GenAI tools, and the overall user experience of the Jerry super app.
- • **Engage Directly with Customers and Lead by Example:** To stay sharp and deeply connected to the customer journey, you will actively participate in direct customer engagement. This includes stepping onto the front lines to assist customers, simplifying complex insurance jargon, preparing quotes, and even binding policies. By leading through example, you will reinforce best practices, demonstrate empathy under pressure, and ensure the team consistently delivers a tailored and exceptional customer experience.
- • **Contribute to Strategic Growth Initiatives:** Collaborate closely with the broader insurance operations team to identify opportunities for growth. This involves pinpointing gaps in customer coverage, developing strategies to increase new business policy sales, and implementing initiatives to enhance customer retention. Your insights will be crucial in shaping the future growth trajectory of Jerry.ai.
- • **Foster a Culture of First-Principles Thinking:** At Jerry.ai, we value individuals who don't just follow processes but understand the fundamental 'why' behind them. You will encourage your team to question assumptions, identify inefficiencies, and propose innovative solutions. This approach is key to building better, more effective processes and staying ahead in a dynamic market.
- • **Onboard and Develop Top Talent:** You will play a critical role in identifying, recruiting, and onboarding new high-caliber sales agents. Furthermore, you will be responsible for conducting performance reviews and creating development plans to ensure continuous learning and career progression for your team members, contributing to a talent-dense environment that prioritizes rapid career acceleration.
- • **Navigate Ambiguity and Drive Execution:** As part of a pre-IPO startup experiencing exponential growth, you must be comfortable operating in an environment with inherent ambiguity. You will need to seamlessly transition between high-level strategic thinking and hands-on, day-to-day execution, ensuring that objectives are met efficiently and effectively.
- • **Be a Customer Advocate:** Champion a customer-first culture within your team. You will instill the importance of empathy, trust, and clarity in every customer interaction, ensuring that Jerry.ai is not just a service provider but a trusted partner in simplifying car ownership.
- • **Leverage Technology for Efficiency:** Become proficient with and advocate for the use of our CRM tools and omni-channel communication platforms. You will ensure your team effectively utilizes these technologies to streamline workflows, enhance customer communication, and improve overall productivity.
- • **Contribute to a Disruptive Vision:** Be part of a mission to disrupt a massive market and contribute to scaling Jerry.ai into a $10 billion business. Your role is pivotal in revolutionizing how people manage one of their most significant assets – their car.
🎯 Requirements
- • Minimum of 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 is required, or a strong willingness and ability to obtain one quickly.
- • Strong technical aptitude and comfort with CRM tools and omni-channel communication platforms.
🏖️ Benefits
- • Competitive compensation package including base salary and commission, ranging from $100,000 - $150,000 per year.
- • Comprehensive health, vision, and dental insurance plans.
- • Generous paid time off (PTO) and paid parental leave.
- • 401(K) plan with employer matching for retirement savings.
- • Remote work flexibility with provided equipment.
Skills & Technologies
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.
