Top Tech Jobs & Startup Jobs in Chicago, IL

Partner with product, marketing, and biz-dev to drive data-driven growth. Design, run, and analyze A/B tests; use ML and analytics to inform acquisition and partnership strategies; automate processes to improve operational efficiency.

Own analytics for a core business area (growth, product, AI, or partnerships): define problems, build metrics/reports, run analyses and experiments, surface insights, and drive cross-functional decisions to improve key business metrics end-to-end.

Lead consolidation and platform strategy for Jerry.ai's AI agent products. Own prompt consolidation, technical prioritization, API and system architecture decisions, OpenAI partnership and ChatGPT store presence, and coordinate engineering, data, and operations while maintaining the current AI platform and driving roadmap execution.

Drive Jerry's organic presence on Reddit, Quora, YouTube, and TikTok. Build community playbooks, grow and moderate subreddits, create scalable authentic engagement strategies using AI, collaborate with Growth and Content, and track sentiment, share of voice, referral traffic, and LLM citation.

Own the analytics function for an embedded business unit: define problems, build reports and experiments, analyze data, surface insights, and drive cross-functional decisions to improve product, growth, AI, or partnerships.

Lead end-to-end performance creative: concept, script, produce, edit, and iterate ads across paid social, CTV, and emerging channels. Translate performance data into creative direction, manage agencies and production partners, and leverage AI tools to speed production while elevating brand quality and measurement-driven results.

Lead end-to-end development and scaling of Jerry.ai's customer-facing Agentic AI platform. Own roadmap, partner with engineering on prompt strategies, evaluation frameworks, and guardrails, drive experiments to improve automation and satisfaction, translate technical concepts across the organization, and collaborate with partners (e.g., OpenAI) to deploy voice models and workflow automation.

Lead development and scaling of a customer-facing AI agents platform. Own roadmap, prompt strategies, evaluation frameworks, and guardrails. Partner with engineering and OpenAI to deploy voice and automation models, improve automation rates and answer quality, and drive experiments using data and SQL.

Lead end-to-end partnerships for Jerry's new product lines (home, motorcycle, etc.): build pipeline, qualify and negotiate with insurance carriers and partners, design creative deal structures, close complex multi-stakeholder deals, ensure partner onboarding and long-term success, and inform vertical strategy through cross-functional collaboration.

Lead consolidation and strategy for a fragmented AI prompt/platform ecosystem, prioritize chatbot work, own OpenAI/ChatGPT integrations, coordinate cross-functional teams, maintain current AI platform operations, and drive decisions on emerging tech like voicebots.