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Insurance Sales & Service Associate (Remote, Tech Startup)

Jerry - Remote - Remote - posted 2026-08-15

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Salary: USD 19 - 21 / hourly

Jerry is a tech-enabled insurance platform modernizing car and home insurance. As an Insurance Sales & Service Associate on the Customer Operations team, you'll be the trusted voice helping customers navigate insurance policies, coverage options, and service requests. Your day-to-day includes answering inbound calls from customers shopping for auto, home, motorcycle, and other policies, as well as supporting existing policyholders with changes and claims. You'll develop deep product knowledge across Jerry's panel of insurance carriers, identifying which policies fit each customer's needs. Beyond transactional support, you'll spot coverage gaps, highlight available discounts, flag upcoming renewals, and process service requests (vehicle changes, driver updates, policy documents). The role blends sales and service—you'll discover during the interview process whether you lean more toward new customer acquisition or retention/support. Either way, you're a problem-solver who catches what customers don't know to ask about. You'll have a direct feedback loop to the product team, seeing your suggestions shipped quickly. Jerry values warm, fast customer experiences and a collaborative team culture. The work is fast-paced and high-energy. You'll work fully remote with flexible scheduling (5-day 8-hour or 4-day 10-hour weeks), and the company provides work equipment. Ideal candidates have prior customer service, sales, or hospitality experience (not required), a genuinely friendly attitude, strong problem-solving and communication skills, and a solid work ethic. Jerry will pay for your P&C insurance license if you don't have one. Compensation for the sales path: $19–$21/hour plus uncapped commissions; top performers typically earn $100k+ annually. Full benefits include medical, dental, vision, 401(k) match, paid time off, and stock options.

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