Jobs at Jerry

Manage day-to-day people operations across onboarding, offboarding, employee files, benefits, compliance, HR documentation, and employee support. Research employment requirements, draft policies, maintain HR records, and partner with managers and HR colleagues. Support engagement initiatives and improve scalable HR processes using automation and AI tools. The role requires independent judgment, confidentiality, strong communication, and hands-on experience across the employee lifecycle.

Own the analytical function for a core business area such as growth, product, AI, or partnerships. Define business questions and metrics, build reports, conduct analyses and experiments, surface insights, and drive leadership decisions and outcomes. The role requires independently structuring ambiguous problems, communicating recommendations persuasively, and executing initiatives end to end.

Lead the architecture and development of Jerry.ai’s next-generation AI agents and workflow automation platform. Build conversational and computer-use agents, document validation, voicebot interactions, and integrations with external insurance systems. Evaluate emerging AI technologies, deploy production LLM systems, and improve reliability, latency, cost, evaluation, and failure handling. Partner with OpenAI on next-generation voice models and automation capabilities.

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 independent analytical problem-solving, strong SQL or Python skills, persuasive communication, and ownership of ambiguous problems with measurable business impact.

Lead the architecture and development of Jerry.ai’s next-generation AI and automation platform. Own conversational agents, voicebots, computer-use agents, backend workflow automation, document validation, transaction orchestration, and external insurance-system integrations. Evaluate emerging AI technologies, deploy production LLM systems, and partner with OpenAI on advanced voice and workflow solutions. The role requires end-to-end software ownership, strong architectural judgment, and experience managing evaluations, regressions, latency, cost, and failure handling.

Own Jerry.ai’s end-to-end partnerships motion for new product lines, including building the pipeline, developing partner value propositions, structuring complex deals, closing agreements, and ensuring post-close success. The role focuses on insurance carriers and distribution partners, contributes to vertical strategy, and requires independently managing senior stakeholders across product, engineering, data science, legal, finance, and executive leadership.

Own the analytical function for a business area such as 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 independently structuring data, solving ambiguous problems, communicating recommendations clearly, and delivering measurable business impact.

Own the analytical function for a business area such as growth, product, AI and automation, or strategic partnerships. Define business questions, metrics, reports, analyses, and experiments; surface insights; and drive data-informed decisions with cross-functional stakeholders. The role requires independent analytical problem-solving, SQL or Python proficiency, strong communication, and ownership of ambiguous initiatives through measurable business impact.

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

Leads data-driven business operations initiatives, including customer and partner growth, product experimentation, acquisition strategy, and process optimization. Partners with marketing, product, and business development teams; designs and analyzes A/B tests; applies machine learning and SQL-based analysis to generate strategic insights and improve operational efficiency.

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 while preserving authenticity. Partner with Growth and Content teams, and measure sentiment, share of voice, referral traffic, and LLM citations. The role requires strong platform fluency, authentic writing, strategic systems thinking, and experience in community management or organic social.

Drive data-informed decisions across growth, product, marketing, and business development initiatives. Responsibilities include analyzing customer and partner performance, designing and evaluating A/B experiments, identifying scalable acquisition and partnership levers, extracting insights with machine learning models, and automating manual processes to improve operational efficiency.

Own the end-to-end customer journey for Jerry’s insurance marketplace, including landing pages, signup and purchase funnels, quote shopping, personalization, customer communications, and cross-product integrations. Partner with engineering, design, analytics, marketing, and leadership to identify opportunities, simplify complex insurance experiences, and deliver products that drive sustainable customer growth.

Own the end-to-end customer growth journey, from landing pages and signup funnels through insurance quote shopping and cross-product integration. Lead discovery, define hypotheses, simplify complex insurance experiences, personalize customer journeys, and deliver high-impact products in partnership with Engineering, Design, Analytics, Marketing, and leadership. The role requires strong customer empathy, analytical ability, communication, and ownership in a fast-paced environment.

Own the strategy, architecture, evaluation, and production delivery of Jerry.ai’s AI agents and workflow automation platform. Lead chatbot, voicebot, computer-use agent, document validation, transaction orchestration, and external system automation initiatives. Evaluate emerging AI technologies, make technical investment decisions, partner with OpenAI, and collaborate closely with engineering and prompt engineering teams. The role requires hands-on experience launching LLM systems and managing evaluations, regressions, latency, cost, and failure handling.

Lead development of next-generation AI systems for insurance automation, including document validation, voicebots, computer-use agents, and complex workflow orchestration. Set chatbot architecture and technical standards, build and deploy production automations, evaluate emerging AI technologies, and partner with OpenAI on voice models. Own LLM system reliability, including evaluations, regression prevention, latency, cost, and failure handling.

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-building, creative experimentation, and measurable growth outcomes.

Manage day-to-day HR operations across the employee lifecycle, including onboarding, offboarding, employee records, benefits administration, compliance, HR documentation, and employee support. Research employment laws, help develop policies, support engagement initiatives, collaborate with HR team members, and improve processes through automation and AI tools.

Own Jerry’s Reddit presence across automotive, finance, and consumer communities. Develop a community voice, create educational posts and guides, manage reputation and crises, track engagement and referral metrics, and share customer insights with Product and Content teams. The role requires authentic Reddit expertise, strong writing, community marketing experience, search awareness, and the ability to handle public skepticism with empathy and transparency.

Create educational, entertaining Reddit content about automotive and financial topics. Write authentic short- and long-form posts, engaging replies, SEO- and LLM-optimized content, and experiment with hooks, formatting, and timing to increase organic reach and community trust. Collaborate with Content, SEO, and Product teams to translate company insights into accurate, Reddit-native messaging.