Top Tech Jobs & Startup Jobs in Chicago, IL

Lead product development and scaling of Jerry.ai's AI agent platform. Define roadmap, design prompt strategies and guardrails, partner with engineering and OpenAI, run experiments to improve automation, answer quality, and customer satisfaction, and establish platform standards and evaluation frameworks.

Lead development and scaling of an agentic AI platform that automates customer sales and service using LLMs, human-in-the-loop feedback, and APIs. Drive roadmap, prompt strategies, evaluation frameworks, guardrails, and partnerships (e.g., OpenAI) to improve automation rates, quality, and customer satisfaction.

Lead end-to-end partnerships for new product lines (home, motorcycle, etc.): build pipeline, structure complex deals with carriers and partners, close agreements, ensure partner onboarding and success, and inform vertical strategy while working cross-functionally.

Support BizOps & Analytics by driving data-driven decisions across growth initiatives: partner with product, marketing, and BD; design and analyze A/B tests; identify scalable acquisition levers; automate manual processes; and leverage advanced ML models to generate actionable insights that shape product and partnership strategy.

Lead Jerry's organic presence across Reddit, Quora, YouTube, and TikTok. Create community playbooks, grow subreddits, develop scalable authentic content and engagement strategies (using AI where helpful), collaborate with Growth and Content, and measure sentiment, share of voice, referral traffic, and LLM citation.

Embedded on a core business team, define the right problems, build metrics and reports, run analyses and experiments, surface actionable insights, and drive data-informed decisions end-to-end across growth, product, AI, or partnerships.

Lead development and scaling of Jerry.ai's customer-facing Agentic AI platform. Define roadmap, partner with engineers on prompt strategies, evaluation frameworks, and guardrails; optimize latency, cost, and accuracy. Drive experiments to improve automation, answer quality, and customer satisfaction, and collaborate with partners like OpenAI to deploy voice models and workflow automation.

Lead organic presence and community growth on Reddit, Quora, YouTube, and TikTok. Build community playbooks, grow subreddits, scale authentic engagement using AI, coordinate with Growth and Content, and track sentiment, share of voice, referral traffic, and LLM citation metrics.

Owner of the customer sign-up and purchase funnel for the car insurance marketplace. Conduct product walkthroughs, synthesize user feedback, triage bugs, run A/B tests and experiments, and lead end-to-end delivery of growth features and launches while coordinating across design, engineering, analytics, and marketing.

Embed within a core business area to define problems, build metrics, run analyses and experiments, surface insights, and drive data-informed decisions end-to-end across growth, product, AI/automation, or partnerships.