Top Tech Jobs & Startup Jobs in Chicago, IL

Build and own analytics and AI-driven reporting for Care Partnerships. Create self-service insights, predict partner health, prioritize outreach, instrument experiments and launch analytics infrastructure to scale referrals and partner relationships.

Lead cross-functional, high-impact initiatives across Product, Data, and Operations. Design and scale 0-1 initiatives, build repeatable processes, analyze complex data to set strategy, drive OKRs, and hire and manage a growing operations team to improve provider and patient outcomes.

Lead development of a unified billing platform and ledger to ensure correct appointment billing, reliable reconciliation, and trusted financial datasets and reports. Own architecture and roadmap for ledger, reconciliation, and data-integrity systems; partner with Engineering, Data, Finance, Accounting, and Compliance to improve payment health, automate reconciliation, and enable accurate, timely close and audit readiness.

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.

Lead development of Headway's brand strategy and creative direction across campaigns, product launches, and experiences. Partner with Customer Insights to ground briefs, run cultural listening, maintain competitive differentiation, steward brand systems and guidelines, build scalable brand tools (including AI agents), educate internal teams, and measure brand health and creative effectiveness to iterate on strategy.

Lead design and implementation of AI-assisted legal operations and knowledge-management workflows. Manage daily legal department operations, project-manage cross-functional company initiatives, evaluate and deploy AI tooling, and track adoption and efficiency. Drive process improvements and stakeholder alignment to scale legal support for a fast-growing healthcare technology company.

Own and publish enterprise contact-center schedules in Verint, manage rosters and headcount across internal and BPO teams, reconcile scheduled vs. invoiced hours, handle exceptions and intraday adjustments, drive quarterly scheduling optimization and policy, and govern AI-assisted scheduling drafts to improve staffing efficiency and agent wellbeing.

Lead design and implementation of Headway's insurance systems (eligibility, pricing, matching, claims). Build data-intensive, ML-powered platforms and automation, mentor engineers, write high-impact code, and improve accuracy and reliability across state and payer complexity to scale insurance-covered therapy.

Lead strategy and execution for Headway’s provider community and content programs. Define member journeys, manage channels and events, build an ambassador program, capture provider stories, and measure engagement to drive business outcomes and provider advocacy.

Owner of HR operations systems and automations enabling HRBPs and managers. Design agentic AI tooling, build dashboards and workflows, automate employee processes, establish AI/Legal/IT guardrails, measure adoption and impact, and iterate to improve org health and manager effectiveness.