Jobs at Jerry

Handle inbound insurance sales calls, understand customer needs, explain coverage and savings opportunities, recommend tailored policies across 55+ carriers, address objections, finalize coverage, and share customer feedback with the product team. The role includes paid P&C licensing, remote work, flexible scheduling, and uncapped commissions.

Own hands-on HR operations including multi-state compliance, policy drafting, annual audits, handbook updates, payroll and benefits escalations, and leave questions. Review HR administration work, improve processes with an AI-native approach, and gradually assume broader day-to-day HR operations ownership. Requires in-house experience managing compliance across multiple states in a fast-paced environment.

Own multi-state HR compliance, policy updates, annual audits, handbook refreshes, and escalated payroll, benefits, and leave matters. Review HR administration work, improve operational processes with an AI-native approach, and grow into managing day-to-day HR operations. The role requires hands-on in-house generalist experience in a small, fast-paced, multi-state environment.

Own the analytical function for a core business area such as growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; generate actionable insights; and influence leadership decisions. The role requires independently structuring data, solving ambiguous problems, communicating findings clearly, and driving recommendations through execution.

Drive data-informed business decisions across carrier growth, product development, user acquisition, and partnerships. Lead A/B experiments, analyze customer and business performance, identify scalable growth opportunities, and automate manual processes to improve operational efficiency. The role partners with marketing, product, and business development teams and requires strong quantitative analysis, SQL, structured problem-solving, and communication skills.

Manage and grow strategic partner relationships, develop business plans and OKRs, identify new partnership opportunities, negotiate mutually beneficial deals, analyze performance data, provide actionable insights, and resolve operational issues. The role collaborates with product, operations, data, and sales teams to execute partnership strategies and accelerate company growth.

Own the analytical function for a core business area such as growth, product, AI and automation, or strategic partnerships. Define business questions and metrics, build reports, conduct analyses and experiments, surface insights, and drive data-informed decisions with cross-functional stakeholders. The role requires independent problem solving, persuasive communication, and end-to-end ownership of ambiguous initiatives.

Own end-to-end data science for a core business area such as growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; generate actionable insights; and influence leadership decisions. The role requires independent analytical work, strong SQL or Python skills, first-principles problem solving, persuasive communication, and ownership of ambiguous problems. Candidates need 6+ years of experience in consulting, investment banking, or high-growth technology.

Own a 0-to-1 product bet across emerging insurance and asset-related products. Responsibilities include researching customer needs, analyzing quantitative and qualitative data, setting priorities, building and launching products, gathering feedback, iterating toward product-market fit, and scaling successful offerings. The role requires strong ownership, consumer product judgment, analytical thinking, and comfort navigating complex, ambiguous domains.

Create authentic, educational Reddit content about automotive and financial topics for relevant communities. Write posts, replies, and long-form copy in a native Reddit voice; simplify complex subjects; experiment with hooks, formats, and timing; optimize content for search and AI citations; and collaborate with Content, SEO, and Product teams. The role requires an active Reddit presence, strong storytelling, and at least three years of copywriting experience.

Own end-to-end analytical functions for growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; surface insights; and influence product, growth, finance, and operations decisions. The role requires strong independent data analysis, first-principles problem solving, clear communication, and ownership of ambiguous business challenges.

Build and grow Jerry’s organic presence across Reddit, Quora, YouTube, and TikTok. Develop channel-specific community engagement playbooks, grow trusted subreddits, create scalable content strategies, and collaborate with Growth and Content teams. Measure sentiment, share of voice, referral traffic, and LLM citation. The role requires authentic platform-native communication, SEO and LLM knowledge, and experience making complex or stressful consumer topics approachable.

Own the analytical function for a business unit spanning growth, product, AI and automation, or strategic partnerships. Define business problems and metrics, build reports, conduct analyses, design experiments, and deliver actionable insights. Partner with product, growth, finance, and operations leaders to influence decisions and drive initiatives from recommendation through execution. The role requires strong first-principles thinking, independent data skills, persuasive communication, and ownership of ambiguous problems.

Work directly with the Cofounder/CEO on high-impact business challenges during rapid growth. Associates will analyze ambiguous problems, develop strategic solutions, and execute initiatives across product, growth, operations, finance, engineering, and data. The program provides broad exposure to company leadership and is intended to accelerate progression into future product, growth, or functional leadership roles.

Own the analytical function for a business area such as growth, product, AI and automation, or strategic partnerships. Define business questions and metrics, build reports, analyze data, design experiments, communicate insights, and drive decisions and outcomes with cross-functional stakeholders. The role requires strong analytical thinking, independent problem-solving, persuasive communication, and end-to-end ownership of ambiguous business challenges.

Work directly with the CEO on high-leverage growth and operational problems across product, growth, finance, engineering, data, and operations. Associates will analyze ambiguous challenges, develop first-principles solutions, execute strategic initiatives, and gain broad exposure to a rapidly scaling startup. The role is designed to accelerate progression toward product, growth, or functional leadership.

Own the end-to-end analytical function for a business area such as growth, product, AI and automation, or strategic partnerships. Define metrics, build reports, analyze data, design experiments, generate insights, and influence product and business decisions. Partner with stakeholders to clarify ambiguous problems, communicate findings, recommend actions, and drive measurable outcomes.

Drive data-informed decisions across growth, product, marketing, and partnerships. Lead A/B experiment design and analysis, identify scalable acquisition and partnership levers, apply machine learning models to extract insights, and automate manual processes to improve operational efficiency. The role partners with cross-functional teams and communicates findings from frontline employees to executive leadership.

Own the analytical function for a business unit across growth, product, AI and automation, or strategic partnerships. Define business questions, metrics, reports, experiments, and analyses; generate actionable insights; communicate recommendations to leadership; and drive execution through measurable outcomes. The role requires independent problem-solving, strong analytical skills, persuasive communication, and ownership of ambiguous, high-impact initiatives.

Own the end-to-end customer journey from initial discovery through insurance purchase and cross-product adoption. Lead landing pages, signup funnels, quote shopping, personalization, customer communications, and carrier integrations. Partner with Engineering, Design, Analytics, Marketing, and leadership to identify opportunities, analyze customer needs, simplify complex experiences, and deliver high-impact products quickly. The role requires strong product ownership, analytical ability, customer empathy, communication, and comfort navigating ambiguity in a fast-paced environment.