Top Tech Jobs & Startup Jobs in Chicago, IL

Owns the design, implementation, monitoring, and scaling of core operational workflows and processes. Identifies efficiency and automation opportunities, leads cross-functional initiatives with product, engineering, payer, and customer experience teams, and uses data analysis to drive actionable insights and business outcomes. The role serves as an operational bridge to product and data teams while supporting high-quality execution and company growth.

Lead compensation analysis and programs, including market pricing, pay ranges, compensation cycles, offers, promotions, equity, budget modeling, and process improvements. Build scalable compensation tools and frameworks, use AI and automation, improve data quality across Workday, Pave, and Carta, and advise HR, Talent Acquisition, Finance, and managers on compensation decisions.

Leads Headway’s consumer communications and social function, including earned media, organic social, content marketing, data storytelling, and cultural relevance. Builds media relationships, manages an agency partner, develops content across blogs, YouTube, and Substack, grows engagement, and leads a small team. Partners with Communications, Brand, Product Marketing, research, and analytics to increase awareness and strengthen Headway’s presence across press, search, social, LLMs, and consumer conversations.

Own the patient Home Base experience across Headway’s iOS, Android, and web platforms. Lead information architecture, navigation, messaging, notifications, app foundations, Android launch, web improvements, and partner-team integrations. Drive engagement and retention through experimentation, analytics, reliable performance, and reduced friction. Collaborate with engineering, design, research, clinical, legal, marketing, and other product teams while ensuring privacy, consent, accessibility, and a coherent patient experience.

Build and refine security detections, logging, telemetry, SIEM pipelines, and incident response capabilities across cloud, corporate, and SaaS environments. Conduct threat hunting, threat modeling, alert triage, and response engineering. Develop automation and AI-assisted security tooling, maintain runbooks and documentation, participate in on-call rotations, and collaborate with engineering and business teams on security initiatives.

Own the architecture and technical direction for provider-sourced client products, including lead management, caseload migration, AI-powered inquiry workflows, and provider marketing tools. Partner cross-functionally with product, design, data, sales, customer experience, and pricing teams. Build reliable user-facing systems, guide technical decisions across teams, measure product impact through experimentation, and influence teams without direct authority.

Lead financial decision-making for provider and patient growth engines. Own the revenue model, forecasting, capital allocation, unit economics, annual planning, monthly forecasting, and GTM headcount and capacity planning. Build and lead the GTM Finance function, including hiring, coaching, analytical infrastructure, dashboards, reporting, and AI-enabled workflows. Partner with business leaders to evaluate CAC, LTV, payback, channel performance, and growth investment decisions.

Leads and coaches a team of 6–7 recruiters supporting Provider Sales and Care Partnerships. Owns recruiting strategy, complex requisitions, sourcing, process design, pipeline health, offer closing, recruiting metrics, stakeholder partnerships, interviewer training, and process improvement. Serves as an executive-facing talent advisor while driving consistent, inclusive, data-informed hiring practices in a high-growth environment.

Own the strategy and execution of new payer partnerships with U.S. health plans. Lead contract expansion, including value-based arrangements and lines of business, while shaping scalable mental healthcare networks and expanding affordable coverage. The role requires deep payer economics knowledge, end-to-end business development experience, strong relationship-building skills, operational excellence, and the ability to navigate ambiguity and drive strategic outcomes.

Lead Headway’s Infrastructure team, owning AWS cloud infrastructure, deployment pipelines, LLM platform capabilities, databases, observability, reliability, and incident response. Hire and develop engineers, establish self-service platform practices, reduce incident blast radius, define production readiness for AI workloads, and partner with Security and product engineering teams. The role combines technical leadership, people management, platform strategy, design reviews, and hands-on incident response.