Supervisor, Insurance Sales

📋 Description

• • Are you a dynamic and results-driven leader with a passion for building and scaling high-performance sales teams? Do you thrive in a fast-paced, innovative environment where your contributions directly impact growth and customer success? Jerry Technologies, Inc. is seeking an exceptional Supervisor, Insurance Sales to join our pre-IPO startup and play a pivotal role in disrupting the massive car ownership market. This is a unique opportunity to be part of a rapidly growing company, backed by significant capital ($240M funded), experiencing explosive revenue growth (60X in 5 years), and operating within a $2T market. You'll collaborate with a world-class team comprised of talent from leading companies like McKinsey, Amazon, BCG, and Nvidia, all dedicated to scaling Jerry into a $10B business.
• • As a Supervisor, Insurance Sales, you will report directly to the Director of Contact Center Operations and serve as a critical player-coach. Your primary responsibility will be to guide and empower a team of Insurance Sales Agents to achieve exceptional results. At Jerry, our mission extends beyond simply selling insurance; we are dedicated to simplifying the most complex and often expensive aspects of car ownership for our rapidly growing base of over 5 million customers. You will be instrumental in ensuring your team delivers a tailored, seamless, and positive experience for every customer. This role acts as the vital link between front-line sales execution and overarching operational strategy. You will not only coach your team to meet and exceed aggressive sales targets but also partner closely with our Product and Engineering teams to shape and build the future of the Jerry super app.
• • Your impact will be multifaceted and significant. You will cultivate a culture of excellence through rigorous performance coaching, which includes conducting regular call audits, meticulously tracking key performance indicators (KPIs), and providing comprehensive monthly coaching sessions focused on talent development and skill enhancement. You will manage the day-to-day operations of your assigned sales squad, overseeing critical functions such as scheduling, conducting performance reviews, and ensuring a smooth and effective onboarding process for new, high-caliber hires. Furthermore, you will be a key contributor to operational excellence by providing direct, actionable feedback to Product Managers and Engineering teams. This feedback will be crucial for enhancing our internal Standard Operating Procedures (SOPs), refining our GenAI tools, and improving the overall Jerry app experience for both agents and customers.
• • To stay sharp and maintain a deep understanding of the customer journey, you will also engage in direct customer interactions. Leading by example, you will occasionally step onto the front lines to simplify complex insurance jargon, prepare accurate quotes, and bind policies. This hands-on approach ensures you remain acutely aware of the customer experience and can effectively guide your team. In terms of growth strategy, you will collaborate extensively with various insurance operations teams to identify potential gaps in coverage offerings and proactively seek opportunities to increase new business policy sales and enhance customer retention rates. You are a proven leader with a track record of coaching, mentoring, or managing sales teams in high-velocity environments. Your ability to think using first principles—understanding the fundamental 'why' behind processes and identifying areas for improvement—is essential. You are inherently results-oriented, driven by metrics, and adept at holding your team accountable to a high standard of performance. Your communication skills are exceptional; you can articulate complex insurance concepts with clarity and maintain a professional, empathetic demeanor, even under pressure. Adaptability is key, as you will thrive in the inherent ambiguity of a fast-growing startup, seamlessly transitioning between high-level strategic thinking and hands-on, tactical execution. Above all, you are customer-obsessed, genuinely committed to making the car ownership and insurance purchasing process less painful and more transparent for our users, championing a customer-first culture where every interaction builds trust and loyalty. You are excited by the prospect of joining a talent-dense environment that prioritizes first-principles thinking and offers rapid career acceleration.