Underwriter, Home Insurance

Why Jerry.ai?

• Join a pre-IPO startup with capital, traction, and runway ($240M funded | profitable | 60X revenue growth in 5 years | $2T market size)

• Work closely with brilliant teammates from companies like McKinsey, BCG, Bain, GEICO, Lemonade, Better, Nerdwallet, a16z

• Opportunity to take us to a $5B business and a household name in the next few years

• Be immersed in a talent-dense environment, greatly accelerate your learning and career growth

About the role:

We are looking for our founding Underwriter, Home Insurance to help us build and scale our new home insurance product. We need someone with expertise in home insurance to guide our product research and development journey. This is a very cross-functional role that blends deep industry knowledge, operational attention to detail, and strategic thinking. You will work closely with product managers, designers, software engineers, data scientists and our operations teams. This is a big investment for our business to expand into the home insurance market so you will also work very closely with our executive leaders and founders. You'll be responsible for ensuring the quality and reliability of our home insurance experience, supporting underwriting accuracy and sales efforts, and helping us become a $10B company in the next few years.

How you’ll make an impact:

• Partner with Product, Data, and Engineering to build and maintain lovable home insurance product flows

• Research and provide strategic recommendations on home insurance product offerings, especially for products subject to complex regulatory requirements

• Support agents with product knowledge and training, resolve underwriting issues, and partner with agent leadership to identify opportunities and develop targeted training to enhance sales effectiveness.

• Lead regular quality reviews of the customer experience, proactively identifying opportunities for optimization—and partnering with Product and Operations to implement them.

• Stay on top of home insurance market trends, carrier strategies, and regulatory shifts to inform product and business decisions.

Key responsibilities:

• Strategic thinking

  • Apply a business-oriented mindset to help our Home Insurance Product team evaluate how product improvements impact customer experience, sales growth, and operational scalability.

  • Proactively identify opportunities to enhance our home insurance product strategy in line with broader company objectives.

  • Bring data, research, and user insights to support strategic recommendations.

• Provide subject matter expertise

  • Maintain a deep understanding of the U.S. home insurance market—including product types, pricing dynamics, and regulatory frameworks.

  • Stay current on major carriers, how they differentiate, their distribution strategies, and target segments.

  • Track market trends, emerging competitors, and macroeconomic factors shaping the home insurance landscape.

• Product quality oversight

  • Partner with Product, Data, and Engineering to build and maintain lovable home insurance product flows

  • Proactively monitor the home insurance experience across our app, phone, and web platforms to identify issues and escalate to the product lead to resolve product issues quickly

  • Conduct ongoing quality control audits to ensure the customer journey is seamless and all touch points function as intended.

• Support underwriting, sales and service agents

  • Act as a subject matter expert for home insurance to help agents succeed—by sharing product knowledge, carrier-specific insights, and compliance nuances

  • Partner with our sales team to support, monitor, and help optimize home insurance sales efforts.

  • Identify knowledge and capability gaps related to home insurance within the agent team and support the agent team leadership in the development of targeted training materials to address them.

  • Investigate and resolve home underwriting issues flagged by our agent team, including identifying whether problems are carrier-specific or systemic across the industry.

• Market & regulatory research

  • Conduct research and make recommendations on home insurance product offerings, especially for complex products

  • Stay up to date on state-by-state regulatory requirements impacting product design and distribution.

  • Collaborate with Legal team on compliance and mitigating risk in our product

What we're looking for:

• 4+ years of underwriting or operations experience in home insurance at a top home insurance carrier or insurtech company

• Strong sense of ownership — you're not just here to maintain the status quo; you're here to help us grow and improve.

• You obsess over the details because you know that’s the difference between good and great for both our customer and for our business

• You can effortlessly explain complex insurance topics to a wide range of audiences

• Prior experience weathering a scrappy startup is a bonus!

Why you’ll love it here:

• Opportunity to shape the future of a growing home insurance business at a fast-scaling, high-tech company.

• Work alongside smart, mission-driven teammates who care deeply about improving insurance.

• Competitive compensation and benefits.

• Remote-friendly with flexibility and ownership.

While we appreciate your interest and application, only applicants under consideration will be contacted.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai

About Jerry.ai:

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 their 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 Store. We have more than 5 million customers — and we’re just getting started. 

Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.

Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.