Jobs at Jerry

Owns the P&L, strategy, product development, customer growth, partnerships, and operations for a new business within Jerry.ai. The General Manager will scale an emerging product line, work closely with the CEO and executive team, and initially lead a small team. Candidates need 6+ years in venture capital, private equity, or hands-on startup operating roles, a bachelor’s degree, and the ability to work in person in Palo Alto.

Own the operating model, budgeting, forecasting, variance analysis, and executive financial reporting. Build financial cases for new products, markets, channels, partnerships, and vendor spending. Evaluate unit economics, capital allocation, and build-buy-partner decisions while supporting corporate development and investor diligence. Lead business reviews, improve planning systems, and establish scalable finance processes for a high-growth company.

Conduct legal research on regulatory, consumer protection, insurance, privacy, licensing, and other business issues. Draft and review partner and vendor contracts, support negotiations, product and compliance reviews, regulatory inquiries, licensing requirements, and legal policies. Translate complex legal analysis into practical recommendations, manage deadlines, investigate escalations, and help build scalable compliance systems for the business.

Own legal operations and compliance activities across the US and Canada, including entity filings, regulatory projects, contract reviews, IP protection, consumer escalations, product compliance reviews, and audits. Build AI- and low-code-enabled workflows to automate legal processes, maintain accurate deadlines, investigate compliance risks, and coordinate solutions with Legal, Engineering, Product, and company teams.

Own the operating model, budgeting, forecasting, variance analysis, and executive financial reporting. Build financial cases for new products, markets, channels, and partnerships; evaluate unit economics, capital allocation, and vendor spend. Support corporate development, investor diligence, and build-buy-partner decisions. Lead business reviews and help implement a planning system while partnering with executives and functional leaders.

Own legal operations including entity compliance, intellectual property protection, consumer escalations, product compliance reviews, audits, legal research, and contract reviews. Build AI- and low-code-powered workflows to automate manual legal tasks, maintain accurate filings and deadlines, investigate compliance issues, and partner with Engineering and Product to resolve risks.

Associate Counsel will draft and negotiate commercial agreements, advise on insurance, consumer protection, privacy, products, and regulatory requirements, investigate consumer escalations, support compliance and risk management, and handle licensing and corporate matters. The role requires independently managing legal matters, providing practical recommendations, coordinating with business stakeholders, improving legal processes, and escalating novel or higher-risk issues to Legal Counsel.

Own hands-on HR operations across multi-state compliance, policy drafting, payroll, benefits, leave escalations, audits, and handbook updates. The role will review HR administration work, improve processes using an AI-native approach, and gradually take ownership of daily HR operations. Candidates need at least two years of in-house HR generalist experience, direct multi-state compliance exposure, payroll and benefits experience, and a bachelor's degree.

Own the operating model, budgeting, long-range planning, forecasting, variance analysis, and executive financial reporting. Build financial cases for new products, markets, channels, and partnerships; evaluate unit economics, capital allocation, and build-buy-partner decisions. Support corporate development, vendor spend underwriting, planning-system implementation, and monthly business reviews. Partner closely with executives, founders, functional leaders, investors, and the CFO.

Own hands-on HR operations across multi-state compliance, policy drafting, payroll, benefits, leave escalations, audits, handbook updates, and process improvement. The role will lead the annual compliance audit and handbook refresh, review HR administration work, resolve complex employee questions, and help redesign HR operations using AI. Requires in-house generalist experience in a fast-paced, multi-state environment.

Own and redesign Jerry’s post-purchase customer experience across document verification, payments, policy changes, renewals, re-shopping, and issue resolution. The role focuses on improving retention and accelerating growth from 5 million to 50 million customers. Responsibilities require strong consumer product instincts, data-driven analysis, ownership, and collaboration with founders and cross-functional teams in a high-growth startup environment.

Own end-to-end data science for a business area such as growth, product, AI, or strategic partnerships. Define business questions, metrics, reports, analyses, and experiments; generate actionable insights; and influence product, growth, finance, and operations decisions. The role requires independently structuring ambiguous problems, using SQL or Python, communicating findings clearly, and driving measurable business outcomes.

Own end-to-end business operations and analytics for a core business area such as growth, product, AI, automation, or strategic partnerships. Define business questions, establish metrics, build reports, conduct analyses and experiments, communicate insights, influence leadership decisions, and drive initiatives through execution. The role requires strong analytical thinking, independent data work, persuasive communication, and ownership of ambiguous problems.

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

Own end-to-end data science for growth, product, automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; generate actionable insights; and influence product, growth, finance, and operations decisions. The role requires strong SQL or Python skills, independent analytical problem-solving, clear communication, and ownership of ambiguous initiatives.

Build and scale new product verticals under direct mentorship from the CEO. Identify customer problems, execute product and growth initiatives, navigate operational complexity, and collaborate across product, operations, finance, engineering, and data. The role offers broad exposure to startup strategy and execution, with potential progression into product or commercial leadership.

Work directly with the CEO on high-leverage business problems during Jerry's rapid growth. Rotate across product, growth, operations, finance, engineering, and data; develop broad business expertise; and help scale new business lines. The program is designed to prepare successful candidates to own P&L for a business line.

Own the full performance-creative lifecycle across paid social, CTV, and emerging channels. Develop concepts, scripts, hooks, briefs, and creative frameworks; direct production; edit video; interpret performance data; and iterate ads for measurable results. Manage agencies and production partners while elevating brand quality, visual storytelling, and creative volume. Use AI tools to accelerate ideation, scripting, editing, and asset generation.