Jobs at Jerry

Work directly with the CEO on high-impact business challenges during Jerry’s rapid growth. The role provides exposure to product, growth, operations, finance, engineering, and data, with responsibility for executing company-wide strategies and scaling new business lines. Successful candidates may eventually own P&L for a business line.

Own the end-to-end creation of performance-driven advertising across paid social, CTV, YouTube, and emerging channels. Responsibilities include concepting, scripting, directing production, video editing, developing performance-focused creative frameworks, interpreting data, managing agencies, and using AI tools to accelerate production. The role combines elevated visual taste, brand development, creative experimentation, and measurable growth outcomes.

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 the analytical function for a business unit spanning growth, product, AI and automation, or strategic partnerships. Define business problems, establish metrics, build reports, run analyses and experiments, surface insights, and drive decisions through execution. The role requires solving ambiguous problems, independently structuring and interpreting data using SQL or Python, communicating findings clearly, and influencing leadership and cross-functional stakeholders.

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.

Conduct legal research and translate regulatory, consumer protection, insurance, privacy, and licensing requirements into practical business recommendations. Draft and review partner and vendor agreements, support negotiations, product and compliance reviews, regulatory inquiries, consumer escalations, policies, procedures, and compliance systems. Collaborate with Legal, Product, Engineering, Operations, and business leaders while managing multiple matters, deadlines, and emerging legal issues.

Own end-to-end data science and analytics for growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, analyses, reports, and experiments; surface insights; and influence product, growth, finance, and operations decisions. The role requires independently structuring data, solving ambiguous problems, communicating findings clearly, and driving measurable business outcomes.

Lead insurance compliance operations, including critical complaint escalations, state Department of Insurance responses, carrier audits, complaint-log controls, regulatory reporting, and claims support. Partner with Legal, Product, and Engineering to resolve systemic issues, implement compliance improvements, maintain audit-ready records, and coach teams. The role requires strong knowledge of P&C insurance regulations, NAIC standards, state insurance codes, and market conduct examinations.

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 end-to-end data science for growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; generate insights; and drive recommendations and decisions with cross-functional stakeholders. The role requires strong SQL or Python skills, independent analytical problem-solving, ownership of ambiguous initiatives, and persuasive communication with leadership.

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.

Develop product-building skills while working directly with the CEO to build and scale new product verticals. Responsibilities include identifying customer problems, executing growth and operational strategies, collaborating across product, engineering, data, finance, and operations, and helping scale new businesses. The role is an intensive pathway toward product or commercial leadership.

Own the analytical function for a business unit spanning growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, experiments, and analyses; surface actionable insights; communicate recommendations; and drive decisions and execution with cross-functional stakeholders. The role requires independent data skills, first-principles problem solving, persuasive communication, and ownership of ambiguous initiatives.

Associate Counsel will draft and negotiate commercial agreements, advise on insurance, consumer protection, privacy, product, and regulatory matters, handle consumer escalations and inquiries, support compliance and risk programs, and manage licensing and corporate legal issues. The role requires independent matter ownership, practical legal judgment, strong communication, and collaboration with business stakeholders in a technology company.

Build and scale new product verticals while working directly with the CEO and executive team. Identify customer needs, execute product strategies, collaborate across product, growth, operations, finance, engineering, and data, and help drive rapid company growth. The role offers mentorship from a serial founder and a path toward product or commercial leadership.

Lead a newly launched business, owning its P&L, strategy, product development, customer growth, partnerships, and operations. Report to the CEO and scale a new product line within a fast-growing startup, potentially managing a small team. The role requires hands-on ownership, urgency, resilience, and the ability to operate across functions. Candidates need 6+ years in venture capital, private equity, or hands-on operating roles at fast-growing startups, plus a bachelor’s degree and availability to work in person in Palo Alto.

Own the strategy, execution, and scaling of emerging consumer products across insurance, property taxes, and asset ownership. Responsibilities include ramping quickly in new domains, analyzing quantitative and qualitative insights, prioritizing product opportunities, building and launching products, gathering customer feedback, iterating, and driving product-market fit. The role requires strong ownership, analytical thinking, consumer product instincts, empathy, and diligent follow-through.