Jobs at Jerry

Handle inbound insurance sales and service calls, help customers select appropriate coverage, process policy changes and documentation, solve problems, and provide product feedback. The role serves auto, home, motorcycle, and other insurance customers. Prior customer service or sales experience is helpful but not required; training and P&C licensing support are provided.

Work directly with the CEO on high-leverage business problems during rapid company growth. The associate will evaluate opportunities, develop solutions, execute initiatives, and gain exposure to product, growth, operations, finance, engineering, and data. The role offers mentorship and broad operating experience, with potential progression into product, growth, or functional leadership.

Works directly with the CEO on high-impact business problems during rapid company growth. The associate will evaluate and execute initiatives across product, growth, operations, finance, engineering, and data, while developing broad leadership experience. The program seeks owners who think from first principles, act with urgency, and persist through ambiguity, with potential progression into product, growth, or functional leadership.

Handle inbound insurance sales calls, understand customer needs, explain coverage and savings opportunities, create tailored policies across 55+ carrier partners, and finalize coverage. Build trust through empathetic consultation, address purchasing concerns, provide exceptional customer service, and share customer feedback with the product team. The role includes paid P&C licensing, remote work, flexible scheduling, commissions, and benefits.

Leads insurance compliance operations, including complex customer escalations, state Department of Insurance complaints, carrier audits, regulatory correspondence, complaint logs, and audit-ready documentation. Partners with Legal, Product, and Engineering to address root causes, implement compliance controls, and improve operational processes. Provides coaching and quality oversight while managing regulatory deadlines, carrier relationships, and claims-related investigations.

Handle inbound insurance calls, assess customer needs, explain coverage options, create tailored policies across 55+ carriers, address purchasing concerns, bind coverage, and provide feedback to improve Jerry’s product and customer experience. The role offers paid P&C licensing, remote work, training, flexible scheduling, benefits, and uncapped commissions.

Manage day-to-day HR operations across the employee lifecycle, including onboarding, offboarding, benefits, employee records, compliance, HR documentation, and employee support. Research employment law, assist with policy development, support engagement initiatives, answer HR process questions, and improve workflows using HRIS platforms, automation, and AI tools. The role requires independent judgment, confidentiality, strong communication, and experience supporting HR operations in a growing organization.

Manage day-to-day people operations across onboarding, offboarding, employee files, benefits, compliance, HR documentation, and employee support. Research employment law, maintain compliant processes, draft policies, answer employee questions, support engagement initiatives, and improve HR workflows using automation and AI tools. Partner with hiring managers and HR colleagues while independently handling sensitive employee information and operational priorities.

Lead data-driven business operations initiatives, including customer and partner growth, product experimentation, acquisition strategy, and process automation. Partner with marketing, product, and business development teams; design and analyze A/B tests; use SQL and machine learning models to generate insights; and communicate recommendations to stakeholders from frontline teams through executives.

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; surface insights; and drive recommendations and decisions with cross-functional stakeholders. The role requires independent data work, strong analytical thinking, clear communication, and ownership of ambiguous problems that deliver measurable business impact.

Create authentic, educational Reddit content about automotive, insurance, and financial topics. Write posts, titles, guides, replies, and community engagement copy tailored to subreddit culture. Experiment with formats, hooks, and timing to increase organic reach, optimize content for search and AI citations, and collaborate with Content, SEO, and Product teams. The role requires strong Reddit expertise, three or more years of copywriting experience, and the ability to translate complex subjects into clear, useful writing.

Own the analytical function for a business unit across growth, product, AI, automation, or strategic partnerships. Define business questions and metrics, build reports, run analyses, design experiments, surface insights, and drive decisions through execution. The role requires independent data work, first-principles problem solving, persuasive communication, and ownership of ambiguous, high-impact initiatives.

Own the analytical function for a core business area such as growth, product, AI and automation, or strategic partnerships. Define business questions, metrics, reports, analyses, and experiments; surface insights; recommend actions; and drive execution with cross-functional stakeholders. The role requires solving ambiguous problems, influencing leadership decisions, and delivering measurable business impact.

Build and grow Jerry’s organic presence across Reddit, Quora, YouTube, and TikTok. Develop channel-specific community playbooks, grow trusted subreddits, and create scalable content and engagement strategies that preserve authenticity. Collaborate with Growth and Content teams, leverage AI, and measure sentiment, share of voice, referral traffic, and LLM citations. The role requires platform-native communication, strategic operations, SEO knowledge, and experience humanizing complex or regulated consumer categories.

Own the analytical function for a business unit spanning growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; surface insights; and drive data-informed decisions with cross-functional stakeholders. The role requires independent data work, strong analytical reasoning, persuasive communication, and ownership of ambiguous problems through measurable business impact.

Create educational, entertaining Reddit content about automotive and financial topics. Write authentic posts, replies, and SEO-optimized material; test hooks and formats; engage communities; and collaborate with Content, SEO, and Product teams to build trust and organic reach.

Drive data-informed decisions across business initiatives, including carrier growth, product launches, user acquisition, and partnerships. Lead A/B experiment design and analysis, identify profitable growth levers, generate customer and business insights, and automate manual processes to improve operational efficiency. Collaborate with marketing, product, and business development teams while communicating recommendations to audiences ranging from frontline employees to executives.

Own the analytical function for a business unit across growth, product, AI and automation, or strategic partnerships. Define business questions, metrics, reports, analyses, and experiments; surface insights; recommend actions; and drive decisions and outcomes with cross-functional leadership. The role requires strong independent data skills, first-principles problem solving, persuasive communication, and ownership of ambiguous high-impact initiatives.

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; influence leadership decisions; and drive initiatives through execution. The role requires strong analytical, communication, ownership, and problem-solving skills, with experience in consulting, investment banking, or high-growth technology.

Own Jerry’s Reddit presence across automotive, finance, and consumer communities. Develop platform-native content, community guidelines, reputation management, and crisis responses while building trust through helpful engagement. Track karma, sentiment, referral traffic, share of voice, search visibility, and LLM citations. Translate Reddit insights and car-owner pain points into feedback for Product and Content teams.