Jobs at Jerry

Own the post-purchase customer experience for Jerry’s insurance marketplace, including document verification, payments, policy changes, renewals, re-shopping, and issue resolution. The role focuses on redesigning the customer journey, using data to identify opportunities, and accelerating growth from 5 million to 50 million customers. The ideal candidate brings consumer product instincts, analytical ability, ownership, urgency, and experience in consulting, finance, venture capital, or high-growth startup product development.

Lead a newly launched business, owning its P&L, strategy, product development, customer growth, partnerships, and operations. Report to the CEO and scale the business with support from a small team. Candidates should bring at least six years of venture capital, private equity, or hands-on startup operating experience, a bachelor’s degree, and the ability to work in person at the Palo Alto office.

Work directly with the CEO on high-leverage business challenges during Jerry’s rapid growth. The GM-in-Training will gain exposure to product, growth, operations, finance, engineering, and data; help scale new business lines; and develop the skills to eventually own P&L for a business.

Own the operating model, budgeting, forecasting, variance analysis, and executive financial reporting. Evaluate new products, markets, channels, partnerships, and vendor spend through financial modeling and unit economics. Support corporate development, capital markets, investor diligence, and build-buy-partner decisions. Partner with executives and functional leaders to improve capital allocation and planning processes, including evaluating and implementing a planning system.

Own hands-on HR operations, including multi-state compliance, policy updates, annual compliance audits, handbook refreshes, payroll and benefits escalations, leave questions, and process improvement. The role also reviews HR administration work, helps integrate AI into HR operations, and grows into broader day-to-day HR operations management. Candidates need in-house generalist experience, strong judgment, and comfort handling payroll, benefits, and compliance in a fast-paced, multi-state environment.

Own the operating model, budgeting, long-range planning, forecasting, variance analysis, and executive reporting. Evaluate new products, markets, channels, partnerships, and vendor spend through financial modeling and unit economics. Support corporate development, capital allocation, planning-system implementation, and business reviews while partnering with executives and functional leaders.

Own the operating model, budgeting, forecasting, variance analysis, and executive financial reporting. Evaluate new products, markets, channels, partnerships, and vendor spending through financial modeling and unit economics. Support corporate development, capital markets, and build-buy-partner decisions. Lead business reviews, improve planning processes, and translate complex analysis into actionable insights for executives, founders, the board, and investors.

Own hands-on HR operations, including multi-state compliance, policy drafting, annual audits, handbook updates, payroll, benefits, leave escalations, and process improvement. Review and unblock payroll and HR administration work while helping redesign HR operations with an AI-native approach. The role requires in-house generalist experience and will grow into broader day-to-day HR operations ownership.

Own legal operations including entity compliance, intellectual property protection, consumer escalations, product compliance reviews, regulatory research, contract reviews, and audits across the US and Canada. Build AI- and low-code-enabled workflows to automate legal processes, track deadlines, reduce errors, and improve operational efficiency while partnering with Legal, Engineering, Product, and other teams.

Own and scale a new product bet from concept or early launch through product-market fit. Responsibilities include researching customer pain points, analyzing quantitative and qualitative data, prioritizing high-impact opportunities, defining the roadmap, shipping products, gathering feedback, and iterating rapidly. Products may include home, motorcycle, boat, RV, property tax, or other asset-related offerings.