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+ per year (including commission)

• 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 & Casua