Top Tech Jobs & Startup Jobs in Chicago, IL

Lead sourcing and testing new revenue channels by opening early-stage conversations, validating monetization hypotheses, and identifying scalable growth paths. Focus on exploratory AI product monetization and non-core revenue experiments to diversify and accelerate revenue streams.

Own decision quality by evaluating AI-generated decisions, identifying reasoning failures, designing feedback and training loops, defining decision-quality metrics, and collaborating with Product, R&D, and Engineering to improve robustness, explainability, and drift detection.

Execute end-to-end recruiting: source and build pipelines, conduct structured screens, coordinate interviews, maintain pipeline metrics and candidate experience, and improve hiring velocity while preserving hiring standards.

Design and formalize decision frameworks, signal mappings, configuration schemas, and evaluation criteria to produce reusable, system-native decision logic. Collaborate with Product, AI, and Engineering to encode reasoning, identify failure modes, and produce artifacts that inform product and model development.

Lead new enterprise subscription sales and expand ARR across the Middle East. Own full-cycle land-and-expand sales, close multi-year contracts, manage complex buying committees, maintain pipeline and forecast discipline, and engage executive buyers to drive larger deal sizes and market penetration.

Qualify enterprise demand through structured discovery, filter and maintain high-quality pipeline opportunities, and ensure pipeline hygiene before Account Executive engagement to improve close rates and AE productivity.

Support the CEO with documentation, meeting structuring, tracking cross-functional commitments, preparing board and planning materials, scheduling, and maintaining execution dashboards to reduce CEO cognitive load.

Lead design and execution of Rwazi's ecosystem strategy, building network architecture that connects contributors, mappers, clients, and partners. Strengthen multi-stakeholder relationships, create product feedback loops, protect trust capital, and support strategic expansion to increase cohesion, loyalty, and long-term defensibility.

Hands-on director-level product designer for enterprise SaaS who owns the design system, user psychology, dashboards, data visualizations, and habit-forming product mechanics. Designs workflows to drive adoption, retention, referrals, and expansion while partnering with Product, Engineering, Sales, and Customer Success. Prototypes, tests, and refines UX based on analytics and A/B experiments to align design with revenue metrics.

Lead end-to-end design for Sena, an AI-native B2B enterprise platform. Shape product direction, design AI-first conversational experiences and dashboards, prototype with AI-assisted design-to-code tooling, craft data visualizations, run user research, and collaborate closely with product and engineering to drive adoption and business outcomes.