Top Tech Jobs & Startup Jobs in Chicago, IL

Leads the strategy, roadmap, and execution of search, ranking, matching, and recommendation products for a two-sided marketplace. Oversees algorithmic performance, resource allocation, experimentation, metrics, executive communication, and cross-functional alignment across consumer and enterprise experiences. Coaches product managers and establishes scalable operating rituals while connecting technical improvements to engagement, retention, customer value, and marketplace growth.

Own the end-to-end strategy and roadmap for ExpertApply, an AI-powered job application automation product. Lead mobile-first growth, experimentation, funnel optimization, retention initiatives, and revenue growth. Partner with Engineering, Design, Marketing, Analytics, and leadership to develop features based on market trends, user research, competitive analysis, and quantitative metrics.

Analyze large payment datasets to identify patterns in acceptance, chargebacks, and fraud. Monitor and forecast payment metrics, build financial and statistical models to assess KPI drivers, recommend processor allocation and anti-fraud improvements, and collaborate with development to implement platform changes and reporting tools to optimize e-commerce payment performance.

Lead prompt architecture, governance, and evaluation for consumer-facing career tools. Design multi-agent and chain-of-thought prompt systems, build CI/CD/versioning for prompts, align strategies with engineering and product, establish safety guardrails, evaluate models and tooling, and mentor the prompt management team.