Top Operations & Support Jobs

Provide empathetic customer support to healthcare providers and patients through email, live chat, and phone. Resolve approximately 40 daily operational and technical inquiries, explain Headway’s products and insurance practices, de-escalate challenging situations, and identify customer experience improvements. The role requires weekend availability, remote work from a quiet private workspace, and strong communication, judgment, problem-solving, and goal-oriented performance.

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 AI-powered tools and strategic analytics for Headway’s provider growth and revenue operations. Responsibilities include optimizing provider outreach and conversion, analyzing funnel trends, pipeline health, and cohort performance, supporting weekly business reviews and executive reporting, and enabling sales leaders to self-serve performance insights. The role requires strategic initiative ownership, strong analytical and forecasting skills, and collaboration with revenue leadership in a growth-stage environment.

Owns commercial KPI production, competitive intelligence resources, reporting cycles, and enablement infrastructure for Headway’s payer partnerships organization. The role drives strategic and operational workstreams, coordinates commercial reporting, supports team scaling, and applies AI tools critically to produce reliable recommendations. Success requires strong operational execution, resourcefulness, analytical problem-solving, and comfort working in ambiguity within a digital health environment.

Build, deploy, and iterate AI-powered revenue workflows to automate and scale provider GTM motions. Lead end-to-end Rev Ops initiatives from problem definition and data analysis through implementation, partnering with R&D and Data teams. Shadow reps to design usable processes, measure performance via quantitative analysis, and drive adoption and continuous optimization of AI-native tools and systems.

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.

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.

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.

Lead cross-functional operational initiatives to improve efficiency and scalability. Scope and deliver end-to-end projects, build 0→1 workflows and playbooks, run root-cause analyses using data tools, and align stakeholders to drive measurable pod-level outcomes.