Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end product design for Jerry’s core offerings, ship 0→1 features, partner with research/product/data, build and evolve the design system, apply AI thoughtfully, and raise UX and visual design quality.

Lead and own the AI platform strategy: consolidate prompts across systems, prioritize chatbot work, drive architectural decisions, manage OpenAI/ChatGPT integrations, and translate technical tradeoffs into execution while learning prompt workflows and coordinating engineering, data, and operations teams.

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

Own end-to-end editing of high-volume performance video ads for paid social, CTV, and emerging channels. Cut with performance instincts, iterate quickly using data and feedback, handle motion graphics, basic color and audio mixing, leverage AI-assisted tools, maintain efficient project/version workflows, and QC assets to platform specs and brand standards while collaborating with creative and growth teams.

Lead development and scaling of an AI agent platform to automate customer interactions. Define roadmap, partner with engineering on prompt strategies, evaluation frameworks, and guardrails. Translate technical design across the org, run experiments to improve quality and automation, and work with OpenAI on voice and workflow model integrations.

Embed with a business unit to define problems, build metrics/reports, run analyses and experiments, surface insights, and drive recommendations and execution across growth, product, AI/automation, or partnerships.

Own end-to-end partnerships for new product lines (home, motorcycle, adjacent): build pipeline, structure and close complex multi-stakeholder deals, onboard and drive partner success, and feed partner insights into vertical strategy while working cross-functionally.

Own end-to-end product design for Jerry's consumer web and mobile products. Partner with PMs, engineers, and data teams to simplify data-heavy experiences, create user flows, wireframes, prototypes, and hi-fi UI, evolve the design system, and apply AI to personalize and automate experiences.

Lead consolidation and strategy for a fragmented AI prompt platform, prioritize chatbot and agent work, own OpenAI partnership and ChatGPT presence, and drive platform architecture, migration, and cross-functional execution to scale AI-powered customer experiences.

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