Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Contract Technical Recruiter responsible for full-cycle technical hiring across engineering teams: sourcing, interviewing, closing candidates, partnering with hiring managers and TA team, building strong pipelines, improving processes, and delivering an inclusive candidate experience.

Act as embedded product attorney for engineering and product teams, advising on AI, data use, and multi-state healthcare regulations. Translate complex laws and guidance into practical controls, anticipate regulatory risks, and enable compliant product innovation while partnering cross-functionally.

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.

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.

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.

Full-cycle sales role responsible for recruiting and onboarding therapists and psychiatrists to scale Headway’s provider network. Serve as first point of contact for prospective providers, drive lead generation and conversion, provide product/process feedback cross-functionally, and use data-driven experiments to optimize growth. Compensation includes base salary plus monthly commission.

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 high-volume outbound outreach (phone, email, LinkedIn) to book intro meetings with care management leaders at health systems, qualify prospects, maintain contact lists, hand off leads with context to BD, and iterate on messaging and playbooks to grow Care Partnerships pipeline.

Lead and build Headway's payer marketing function: set strategy, craft positioning and narratives, commercialize payer solutions, translate clinical data into commercial proof, enable sales and field teams, run events and competitive intelligence, and measure relationship and commercial impact.