Top Tech Jobs & Startup Jobs in Chicago, IL

Owns end-to-end accounts payable operations, including invoice processing, payments, accruals, prepaids, reconciliations, and month-end/year-end close. Supports audits, maintains audit-ready documentation, strengthens internal controls, and partners with Accounting and FP&A on accruals, cash forecasting, and vendor issues. The role also drives AP automation, standardizes procedures, optimizes NetSuite and Ramp workflows, and may mentor or manage additional resources as the function grows.

Drive complex cross-functional initiatives, identify operational opportunities, build scalable workflows, analyze data, and deliver measurable improvements. The role owns initiatives from scoping through execution, coordinates stakeholders without formal authority, designs scalable systems and processes, and provides structured recommendations to support pod and organizational priorities.

Leads high-impact business operations initiatives, builds scalable processes and systems, analyzes complex data, partners with Product, Data, and Operations leaders, manages cross-functional execution, mentors team members, and builds a growing operations team to deliver measurable business results.

Own the clinical safety strategy for Headway’s behavioral health platform. Define risk detection, escalation, severity taxonomies, and safeguards across patient and provider product surfaces. Partner with product, engineering, clinical operations, and AI teams to audit safety gaps, evaluate AI outputs, create clinical rubrics, and ensure policies accurately reflect risk ownership. Advocate for clinical rigor while translating complex safety requirements into actionable product systems.

Serve as a strategic finance partner to business functions, translating plans into financial forecasts, budgets, business cases, and investment decisions. Own planning, monthly forecasting, variance analysis, operating budgets, KPIs, and unit economics. Influence capital allocation across product, sales, marketing, operations, hiring, vendors, and build-versus-buy decisions. Apply AI tools to improve financial analysis and decision-making while communicating insights clearly to cross-functional leaders.

Source and engage technical talent, primarily for engineering roles, using LinkedIn Recruiter, Juicebox, Ashby, referrals, talent communities, market mapping, and creative outreach. Partner with recruiters and hiring managers to refine profiles, share market insights, build diverse pipelines, conduct initial candidate screens, and deliver a positive candidate experience in a fast-paced, metrics-driven environment.

Own the strategy and roadmap for patient-provider search, retrieval, ranking, and marketplace matching. Lead experimentation, objective functions, evaluation, and ML platform foundations while partnering with ML engineers, data scientists, design, clinical teams, and executives. Improve successful, lasting care matches rather than optimizing only clicks or bookings. Balance patient access, provider growth, clinical quality, and payer priorities, while setting the standard for technically grounded product management.

Lead Headway’s customer experience operation across Agent Success, Customer Care, Programs, and Systems, managing over 100 employees and 800 partner agents. Own end-to-end support quality, performance, staffing, forecasting, costs, training, QA, procedures, systems, and AI-enabled automation. Partner with Product and R&D to improve customer experience and reduce support demand while developing a high-performing leadership team.

Owns the full business development cycle for mid-market health system partnerships, including prospecting, qualification, pitching, closing, and launch. Builds relationships with care management, population health, and clinical operations leaders; develops account strategies; supports enterprise opportunities; and collaborates with Partner Success, Product, and Operations to ensure successful referrals and launches. Also mentors the BDR team.

Serve as the primary product attorney and regulatory advisor to Product, Engineering, and Operations teams. Provide practical guidance on AI, data use, healthcare technology, clinical modalities, and applicable regulations. Translate complex legal requirements into actionable tools, anticipate regulatory risks, support product innovation, and balance business objectives with risk. Build cross-functional partnerships in a fast-paced healthcare technology environment.