Jobs at Jerry

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 the architecture and production deployment of next-generation AI agents and workflow automation. Own conversational interfaces, voicebots, computer-use agents, document validation, transaction orchestration, and external system integrations. Evaluate emerging AI technologies, optimize LLM systems for reliability, latency, cost, and failure handling, and partner with OpenAI on advanced voice and automation models.

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 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.

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.

Lead the architecture and development of Jerry.ai’s next-generation AI agents and workflow automation platform. Own conversational interfaces, voicebots, computer-use agents, document validation, transaction orchestration, and integrations with external insurance systems. Evaluate emerging AI technologies, deploy production LLM systems, and partner with OpenAI on next-generation voice and automation capabilities. The role requires end-to-end software ownership, attention to evaluation, latency, cost, reliability, and failure handling.

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.

Lead Jerry’s end-to-end partnerships strategy for new product lines, including pipeline development, partner outreach, complex deal structuring, negotiation, closing, onboarding, and post-close success. The role focuses on insurance carriers, product providers, and distribution partners, while contributing market insight to vertical strategy. Success requires building partnerships from zero, navigating complex multi-stakeholder organizations, and collaborating across product, engineering, data science, legal, finance, and executive leadership.

Own end-to-end data science for growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; generate actionable insights; and influence stakeholders and leadership decisions. The role requires independent data work, strong analytical thinking, persuasive communication, and ownership of ambiguous problems through measurable outcomes.

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; surface insights; and drive data-informed decisions and outcomes. The role requires independently structuring and interpreting data, communicating findings to leadership, and solving ambiguous problems using SQL or Python.

Own the end-to-end customer journey for Jerry’s insurance marketplace, from landing pages and signup through quote shopping and cross-product integration. Lead growth product strategy, simplify complex insurance experiences, personalize funnels, build customer trust, and deliver measurable business impact. Partner with Engineering, Design, Analytics, Marketing, Leadership, and the CEO to identify opportunities and rapidly ship products. The role requires strong customer insight, analytical ability, communication, and coordination across global time zones.

Own the customer journey from initial impression through insurance purchase and related product adoption. Lead improvements to landing pages, signup funnels, quote shopping, customer communications, personalization, and integrations with insurance carriers and adjacent products. Partner with Engineering, Design, Analytics, Marketing, and leadership to identify opportunities, interpret customer and business data, simplify complex experiences, and rapidly ship products that drive sustainable customer growth.

Own the strategy, architecture, evaluation, and production deployment of Jerry.ai’s next-generation AI agents and workflow automation platform. Lead conversational agents, voicebots, computer-use agents, document validation, transaction orchestration, and external insurance-system integrations. Evaluate emerging AI technologies, make technical investment decisions, partner with engineering and OpenAI, and ensure systems meet requirements for reliability, latency, cost, regression prevention, and failure handling.

Build and lead next-generation AI systems for automated insurance quoting, customer support, document validation, voice interactions, and external system navigation. Set technical direction for chatbot architecture, evaluate emerging AI technologies, and deploy production LLM systems. Own automation outcomes end to end, including evaluation, regression prevention, latency, cost, and failure handling, while partnering with OpenAI on voice models and workflow automation.

Own end-to-end performance creative across paid social, CTV, and emerging channels. Responsibilities include developing concepts, scripts, briefs, hooks, and creative frameworks; directing production; editing video; translating performance data into creative direction; managing agencies and production partners; tracking platform and cultural trends; and using AI tools to accelerate ideation and asset production.

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.

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.