Jobs at Jerry

Handle inbound customer calls for auto, home, motorcycle, and other insurance policies. Recommend suitable coverage, identify discounts and coverage gaps, process policy service requests, solve customer problems, learn evolving insurance products and the company app, and provide feedback to improve the product. The role offers sales and service paths, with training and payment for a P&C insurance license if needed.

Owns hands-on HR operations, including multi-state compliance, policy and handbook updates, payroll, benefits, leave escalations, and annual compliance audits. Reviews HR administration work, improves processes with an AI-native approach, and grows into broader day-to-day HR operations ownership. Requires in-house generalist experience in a fast-paced, multi-state environment.

Own hands-on HR operations, including multi-state compliance, policy drafting, annual audits, handbook updates, payroll, benefits, leave escalations, and process improvement. The role also reviews HR administration work and develops AI-native approaches to streamline operations. Candidates need at least two years of in-house HR generalist experience, multi-state compliance expertise, and comfort working directly across payroll, benefits, and compliance in a fast-paced startup.

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; surface insights; make recommendations; and drive decisions and outcomes with cross-functional leaders. The role requires strong analytical problem-solving, independent data interpretation, persuasive communication, and ownership of ambiguous, high-impact initiatives.

Leads strategic business development and partnership growth by managing existing relationships, securing new collaborations, negotiating mutually beneficial deals, developing partner business plans, analyzing performance data, identifying growth opportunities, and resolving operational issues. The role collaborates with product, operations, data, and sales teams and reports to the VP of Partnerships.

Own end-to-end analytical work for a business unit spanning growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, experiments, and analyses; surface insights; communicate recommendations; and influence product, growth, finance, and operations leaders to drive measurable outcomes.

Own the end-to-end customer journey from discovery through insurance purchase and beyond. Lead growth initiatives across landing pages, signup funnels, quote shopping, app downloads, personalization, customer communications, and cross-product integrations. Partner with Engineering, Design, Analytics, Marketing, and leadership to identify opportunities, interpret customer and business data, simplify complex insurance experiences, and rapidly ship products that improve customer growth and trust.

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; communicate recommendations; and drive decisions and measurable outcomes with cross-functional stakeholders.

The Business Operations Associate will drive data-informed decisions across acquisition, partnerships, and product initiatives. Responsibilities include analyzing customer and business performance, designing and evaluating A/B experiments, identifying growth and profitability levers, and automating manual processes to improve operational efficiency. The role partners with marketing, product, and business development teams and communicates insights to audiences ranging from frontline employees to executives.

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

Own the analytical function for a core business area such as growth, product, AI, or strategic partnerships. Define business questions, metrics, reports, analyses, and experiments; surface insights; make recommendations; and drive decisions and execution with cross-functional leadership teams. The role requires independent data work, first-principles problem solving, persuasive communication, and ownership of ambiguous, high-impact initiatives.

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

Leads insurance compliance and regulatory operations, including complex complaint escalations, Department of Insurance responses, carrier audits, complaint-log controls, regulatory reporting, and audit-ready documentation. Partners with Legal, Product, Engineering, and Operations to resolve systemic issues, implement compliance improvements, support claims investigations, and coach team members. Requires P&C licensing, substantial insurance and state regulatory compliance experience, knowledge of NAIC regulations and state insurance codes, and strong executive communication skills.

Own end-to-end performance creative for paid social, CTV, and emerging channels. Concept, script, produce, edit, and iterate ads while translating performance data into creative direction. Develop hooks, angles, and frameworks; monitor platform and cultural trends; direct agencies and production partners; maintain high visual and brand standards; and use AI tools to accelerate ideation and production. The role connects creative craft, media strategy, analytics, and scalable growth outcomes.

Own the end-to-end customer acquisition and purchase funnel for Jerry’s insurance marketplace. Lead improvements to landing pages, signup flows, quote shopping, customer communications, personalization, and cross-selling adjacent products. Partner with Engineering, Design, Analytics, Marketing, and leadership to identify opportunities, understand customer needs, simplify complex insurance experiences, and rapidly ship products that drive durable customer growth.

Manage and grow strategic partnerships, serving as the primary partner contact, developing business plans and OKRs, optimizing KPIs through data analysis, negotiating new opportunities, delivering actionable insights, and resolving operational challenges. Collaborate with product, operations, data, and sales teams to execute partnership strategies and accelerate business growth.

Lead data-driven analysis and business operations initiatives across marketing, product, and business development. Design and evaluate A/B experiments, identify acquisition and partnership growth levers, generate customer and performance insights, and automate manual processes. The role requires strong quantitative problem-solving, advanced SQL and data analysis skills, and the ability to communicate recommendations effectively from frontline teams to executives.

Handle inbound insurance sales calls for auto, home, motorcycle, and specialty coverage. Educate customers on policy options, identify savings and coverage gaps, tailor packages across 55+ carrier partners, address concerns, bind policies, and share customer feedback with the product team. The role includes paid property and casualty licensing, remote work, flexible scheduling, training, mentorship, and uncapped commissions.

Own the operating model, annual budget, long-range plan, forecasts, variance analysis, executive reporting, and monthly business reviews. 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 development of scalable finance processes for a high-growth company.

Manage Jerry’s Reddit presence across automotive, financial, and consumer communities. Develop subreddit-specific content, educational guides, memes, and community engagement strategies; handle reputation and crisis management; monitor karma, sentiment, referrals, share of voice, SEO, and LLM citations; and relay customer insights to Product and Content teams. The role requires authentic Reddit fluency, empathy, strategic thinking, and the ability to build trust without overtly promotional messaging.