Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the architecture and development of next-generation AI systems for insurance automation. Build production automations for document validation, record disputes, voice interactions, and external system navigation. Set technical standards for chatbot systems, evaluate emerging AI technologies, partner with OpenAI on voice and workflow solutions, and ensure LLM systems handle evaluation, regressions, latency, cost, and failure scenarios effectively.

Lead the architecture and production deployment of next-generation AI and automation systems for insurance quoting and customer support. Build document validation, voicebot, workflow automation, and external-system navigation capabilities. Set technical standards for chatbot systems, evaluate emerging AI technologies, partner with OpenAI, and ensure reliable LLM operations through evaluations, regression management, latency optimization, cost control, 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 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 product, growth, finance, and operations decisions. The role requires independent data work, strong analytical and communication skills, first-principles problem solving, and ownership of ambiguous initiatives through measurable business impact.

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 insights; communicate recommendations; and drive decisions and measurable outcomes. The role requires independent data work, first-principles thinking, stakeholder influence, and end-to-end ownership of ambiguous problems.

Own end-to-end partnerships for Jerry’s new product lines, including pipeline development, partner outreach, complex deal structuring, negotiation, closing, onboarding, and long-term partner success. The role also contributes to vertical strategy and requires cross-functional collaboration with product, engineering, data science, legal, finance, and executive leadership. Candidates should have experience closing complex multi-stakeholder deals, building partnerships from zero to one, and engaging senior stakeholders.

Own the end-to-end partnerships motion for Jerry’s new product lines, including pipeline development, partner outreach, complex deal structuring, negotiations, onboarding, and post-close success. The role requires building new partnership categories, engaging senior stakeholders, collaborating cross-functionally, and shaping vertical strategy through partner insights. Candidates need 5+ years in business development, partnerships, or strategy consulting, experience closing complex deals, and a track record of building partnerships or functions from zero.

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 product, growth, finance, and operations decisions. The role requires independently structuring data, solving ambiguous problems, communicating findings persuasively, and driving measurable business outcomes.

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 and engagement strategies, collaborate with Growth and Content teams, and measure sentiment, share of voice, referral traffic, and LLM citation. The role requires authentic platform-native communication and experience making complex or stressful consumer categories engaging.

Own Jerry.ai’s end-to-end partnerships motion for new product lines, including pipeline development, partner outreach, complex deal structuring, negotiations, onboarding, and post-close partner success. Build 0-to-1 partnership categories, engage senior stakeholders, shape vertical strategy, and collaborate cross-functionally with product, engineering, data science, legal, finance, and executive leadership.