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Remote Inside Sales Associate (Insurance Tech Startup)

Jerry - Remote - Remote - posted 2026-09-17

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Salary: USD 19 - 21 / hourly

Jerry is an AI-powered insurance platform that simplifies car, home, and motorcycle insurance for customers. The company has grown to 5M+ customers, raised $240M+, and achieved profitability since 2024. You'll join the Customer Operations team in a fully remote role that blends sales and service responsibilities. In this position, you'll handle inbound customer calls from people shopping for auto, home, motorcycle, and other policies, as well as existing policyholders needing changes or support. Your responsibilities include taking excellent care of customers by identifying coverage gaps, uncovering discounts they qualify for, and catching renewal issues before they spike. You'll develop deep product knowledge across Jerry's large panel of insurance partners to match customers with the right coverage. You'll process service requests (vehicles, drivers, lienholders, policy documents), solve problems that remove barriers to proper coverage, and provide feedback to improve the product—with a short feedback loop so you'll see your suggestions ship. The role offers flexibility: choose between a 5-day 8-hour week or 4-day 10-hour week. Work equipment is provided. The company will pay for your P&C insurance license if you don't have one. You'll work alongside a team of talented, kind people from companies like Nvidia, Meta, Amazon, and McKinsey. Jerry is remote-first but also has offices in Palo Alto, New York City, Chicago, and Toronto if you prefer hybrid or in-person work. The company is backed by Y Combinator and consistently ranks among Y Combinator's Top Companies and Forbes/Statista's Best Startup Employers. Requirements: - Prior work experience in customer service, sales, or hospitality is a plus but not required - Genuinely friendly and positive attitude with willingness to work as a team - Strong work ethic - Strong problem-solving skills - Strong communication skills - Must currently reside in one of these states: AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada (full-time salaried); or AZ, FL, GA, NV, NY, NC, TN, TX, UT, VA (full-time hourly)

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