Top Tech Jobs & Startup Jobs in Chicago, IL

Lead development and scaling of Jerry.ai's customer-facing Agentic AI platform. Define roadmap, partner with engineers on prompt strategies, guardrails, and APIs, run experiments to improve automation and answer quality, and work with model partners to deploy next-generation voice and workflow automation.

Lead consolidation and platform strategy for prompt-driven AI products. Own prompt migration onto a unified platform, prioritize chatbot engineering work, define architecture, manage the OpenAI/ChatGPT integrations, and coordinate cross-functional teams to stabilize and evolve the agentic AI platform.

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

Grow Jerry's organic presence on Reddit, Quora, YouTube, and TikTok by building community playbooks, scaling authentic engagement using AI, expanding subreddits, coordinating with Growth and Content, and measuring sentiment, share of voice, referral traffic, and LLM citations.

Own end-to-end partnerships for new product lines: build pipeline, qualify and close complex carrier and distribution deals, design creative deal structures, and ensure partner onboarding and long-term success while informing vertical strategy.

Lead development and scaling of Jerry.ai's agentic AI platform and customer experiences. Define roadmap, design prompt strategies, evaluation frameworks, and guardrails. Partner with engineering and OpenAI to deploy voice and workflow automation models, drive experiments to improve answer quality, satisfaction, and automation rates, and establish AI platform standards.

Embedded in a core business area, you will define problems, build metrics and analyses, run experiments, surface insights, and drive data-informed recommendations end-to-end to improve product, growth, AI/automation, or partnerships metrics.

Embed with a core business unit to define problems, build reports and experiments, analyze data, and drive recommendations end-to-end to improve growth, product, AI/automation, or partnerships. Own metrics, surface insights, and partner with stakeholders to execute decisions and measure impact.

Lead end-to-end development and scaling of Jerry.ai's agentic AI platform. Define roadmap, design prompt strategies, evaluation frameworks, and guardrails. Translate technical requirements across teams, run experiments to improve automation and satisfaction, and partner with OpenAI on voice models and workflow automation.

Embedded in a core business area, own analytics end-to-end: define problems, build reports and experiments, define metrics, surface insights, and drive recommendations that inform product, growth, AI, and partnership decisions.