Top Tech Jobs & Startup Jobs in Chicago, IL

Own Headway’s provider lifecycle marketing program end to end, from segmentation and trigger design through campaign deployment in Iterable and Intercom. Build journeys that improve provider activation, product adoption, engagement, and retention. Develop experiments, define success metrics, analyze performance, and continuously optimize programs. Partner with Product, Product Marketing, Customer Success, and Creative to align lifecycle campaigns with product priorities and create consistent provider experiences.

Leads provider growth marketing to expand Headway’s provider network and improve acquisition efficiency. Owns paid, organic, lifecycle, referral, segmentation, experimentation, channel strategy, and performance measurement. Builds and manages the marketing team while partnering with Sales, RevOps, Finance, Product, and R&D to align growth goals, reduce CAC, optimize provider mix, and develop value-based acquisition frameworks.

Lead data recruiting across Data Science and Data Engineering, managing and developing a team of recruiters. Partner with senior data leaders to design hiring strategies, use metrics and market insights to improve recruiting funnels, and deliver high-quality hiring outcomes. Establish operational standards, prioritize critical hiring initiatives, remove obstacles, and serve as a trusted advisor while building a scalable, high-performing recruiting organization.

Own Headway’s enterprise payer product strategy, partnering with strategic payer accounts, Payer BD, Data, and Engineering. Translate commercial needs into reusable product capabilities, establish a repeatable enterprise product framework, and support procurement, legal, and multi-stakeholder buying processes. The role requires balancing enterprise rigor with startup speed while building the function from scratch.

Drive high-volume outbound outreach through phone, email, and LinkedIn to generate qualified meetings with care management leaders at health systems. Responsibilities include prospect qualification, contact-list development, CRM activity documentation, clean handoffs to the business development team, and collaboration on messaging and outreach strategy. The role also contributes insights on personas, objections, and conversion performance to improve the team's sales playbook.

Own third-party and vendor contracting, AI-assisted contract review, escalated disputes and regulatory inquiries, corporate insurance administration, and other corporate risk matters. Partner with Procurement, Finance, Customer Experience, and Communications in a fast-growing healthcare technology company. Translate legal risks into actionable guidance, manage complex processes, and resolve sensitive matters with sound judgment and strong cross-functional collaboration.

Own Headway’s cloud platform and infrastructure engineering strategy. Lead deployment isolation, container orchestration, AWS networking and compute, autoscaling, capacity planning, Terraform self-service infrastructure, cloud cost attribution, and Python runtime performance. Build reliable paved-road tooling that enables engineering teams to deploy safely and independently while improving scalability, observability, and operational resilience.

Own the roadmap for Headway’s go-to-market systems, automating provider acquisition and consolidating fragmented sales and marketing tools. Partner with sales, marketing, and engineering to improve growth efficiency through AI, automation, revenue feeds, audiences, attribution, data enrichment, and campaign management. Unite cross-functional teams around a shared vision, identify process bottlenecks, and determine when automation, staffing, or incentive changes are needed.

Own complex, senior-level product recruiting searches across Product Management, Product Design, and Product Analytics/Research. Partner with executive product and design leaders on hiring strategy, role definition, talent calibration, sourcing, market intelligence, funnel analytics, structured evaluation, and candidate experience. Advise stakeholders through ambiguous searches, build senior talent pipelines, and improve hiring quality, consistency, and inclusivity across the organization.

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.