Top Tech Jobs & Startup Jobs in Chicago, IL

Lead design and implementation of scalable backend systems that ingest, process, and serve high-volume health data. Own projects end-to-end, drive integrations with third-party APIs, improve data reliability and observability, mentor engineers, and partner with product, clinical, and data teams to deliver clinically meaningful insights.

Lead the technical development and automation of enrollment forecasting models, collaborating with various departments to enhance decision-making and forecast accuracy.

Lead enablement strategy and scalable operations for Customer Success Managers, translating customer and field feedback into roadmaps, resources, AI-enabled workflows, and self-serve tools. Partner cross-functionally to prioritize work that improves customer conversations, retention, and growth while modernizing knowledge management, communications, and intake systems to reduce manual work and increase team efficiency.

Design and build AI-augmented test tooling and automated test infrastructure across mobile, web, and backend. Integrate testing into engineers' workflows (IDE, CI, monitoring, chatops), define quality gates, instrument AI usage and costs, ensure secure handling of PHI, and produce reusable libraries, documentation, and training to help teams adopt automated quality workflows.

Lead national new business growth for enterprise employer segments at Omada Health, focusing on achieving revenue goals and strategic alignment across departments.

Lead cross-functional Engineering, Product, and Design execution for large, complex initiatives. Own integrated launch planning, risk and dependency management, metrics/OKRs, stakeholder alignment, and program rituals to ensure disciplined delivery and measurable business/member impact.

Lead design of AI-supported member and care experiences, defining interaction models, prototyping AI-driven flows, and designing service blueprints. Partner with product, engineering, data, clinical, and research teams to translate AI capabilities into trustworthy, clinically appropriate, and scalable experiences. Create prototypes, design artifacts, evaluation loops, and influence senior stakeholders to align user needs, business goals, and technical constraints.

Lead Omada's investor relations and capital markets strategy as a public company: craft and communicate the equity story, engage investors and analysts, manage earnings and disclosure processes, analyze investor models and ownership trends, and partner with Finance, Legal, and executives on guidance, investor targeting, and capital-markets activities.

Lead end-to-end product design for Omada’s care programs: define problems, create concepts and rapid prototypes, validate with research, and ship consumer-grade mobile (iOS/Android) experiences. Partner with product, engineering, clinical, and data teams, contribute to design systems, and design AI-powered features using AI tools as part of the workflow.

Part-time Director-level HR Business Partner supporting Commercial, Corporate Strategy & Ops, and Finance. Leads organizational design, workforce and capability planning, change leadership, and leadership coaching. Uses AI fluency and people data to inform strategy, redesign roles for human-AI collaboration, streamline HRBP workflows, and measure P&C impact. Partners with centers of excellence and employee relations; advises on complex people issues. Requires travel up to ~25-30% and work during core PST business hours.