Top Tech Jobs & Startup Jobs in Chicago, IL

Own and scale Headway's SEM program across Google and Microsoft Ads, driving campaign architecture, bidding, budget allocation, and performance toward $50M+ annual spend. Design incrementality measurement (geo-lift, holdouts, MMM), partner with Engineering and Data Science on tracking and attribution, optimize post-click conversion with Product, and leverage AI agents to automate keyword expansion, ad copy, and bid signals.

Own and evolve Headway's CX platform: configure voice/IVR and CCaaS routing, deploy AI agent tooling, scale Zendesk/CRM/WFM/QA integrations, run technical programs, and build dashboards to measure system performance and drive operational improvements.

Design, implement, and scale core operational workflows; drive execution strategy and automation; perform data-driven analyses; and lead cross-functional efforts with product, engineering, payer, and CX teams to improve efficiency and operational health.

Own partner health and growth for Headway27s care partnerships by managing executive relationships, running steering committees, leveraging data to identify growth opportunities, and collaborating cross-functionally with Product, Strategy, and Operations to improve partner experience and deepen health system and clinic relationships.

Build and lead Headway's procurement function: define procurement strategy and policy, manage vendor lifecycle, drive cost optimization and strategic sourcing, implement procurement tooling and reporting, advise leadership on governance and risk, and hire and develop a high-impact procurement team.

Run and scale Talent Acquisition enablement and AI-adoption programs: design training and onboarding for recruiters and hiring managers, define success metrics, build dashboards, document processes, and partner cross-functionally to measure and iterate program impact.

Serve as legal partner to the Payer contracting team: own payer contracting strategy, negotiate and review health plan agreements, build scalable legal processes and systems, and collaborate with outside counsel to unlock value while mitigating regulatory and commercial risk.

Lead GTM financial planning and analysis: build and maintain models, own GTM budgeting and forecasting, analyze KPIs and funnel data to evaluate unit economics and channel performance, partner cross-functionally, and produce dashboards and executive-ready reporting to guide resource allocation and growth decisions.

Own and grow a strategic payer commercial relationship by developing senior-level partnerships, shaping patient acquisition channel strategy, collaborating cross-functionally to inform product and operations, driving initiatives to expand demand and stickiness, and documenting scalable commercial playbooks for replication across accounts.

Provide strategic regulatory counsel to Clinical, Product, Engineering, and Operations teams on telehealth, clinical practice, and multi-state healthcare compliance. Draft policy, support audits and remediation, translate complex regulations into practical guidance, anticipate regulatory risks, and enable compliant product innovation while partnering cross-functionally.