Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Lead and scale a regional sales organization in Puerto Rico, managing Sales Managers and a broader sales team to drive new-business acquisition, retention, expansion, pipeline discipline, forecasting, and cross-functional GTM alignment to achieve multi-million dollar revenue targets.

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 strategy and execution for the digital storefront to optimize path-to-purchase and lifetime value. Coordinate cross-functional squads, run advanced A/B experimentation, define metrics and event tracking, prioritize roadmap based on user insights, and collaborate with engineering on technical tradeoffs to drive conversion and revenue.

Lead 0-to-1 retention product initiatives: run deep market and user discovery, validate hypotheses with rapid experiments and MVPs, define strategy and roadmap, partner cross-functionally on GTM and unit economics, mentor PMs, codify launch processes, and advise executives on Go/No-Go decisions.

Drive execution and optimization for Bold.pro by translating product strategy into predictable release cycles. Lead cross-functional teams through discovery, sprint execution, and global launches; analyze product and funnel data to scope feature improvements, define success metrics, and iterate post-launch. Manage dependencies, mitigate risks, and coordinate localization and go-to-market readiness for marketplace and monetization initiatives.

Lead mobile product vision and roadmap, prioritize and execute app features, drive cross-functional alignment, integrate AI/LLM capabilities, define KPIs, run A/B experiments, and deliver personalized mobile experiences that improve user conversion and retention.