Supervisor, Insurance Sales

Company Overview

• 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.

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.

• 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.

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

• 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.

• 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.

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 the 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…