Headway

Accountant

• Support revenue month-end close activities, including preparing journal entries, reconciliations, and account analyses to deliver timely and accurate results
• Contribute to the design, implementation, and documentation of scalable revenue processes, policies and controls to support growth
• Partner with Engineering, Product, Ops and Data teams to develop and test billing and revenue systems
• Analyze large data sets to validate underlying system configurations and financial reporting outputs
• Support annual audit requests and provide documentation for revenue-related testing
• Identify and implement process improvements, leveraging AI tools and automation to drive efficiency in revenue accounting operations
• Lead revenue-related projects, coordinating cross-functional partners, tracking progress, and delivering measurable business impact

Senior Revenue Accountant

Product Designer

• Own the end-to-end payment and billing experience across patients and providers
• Navigate complexity with systems thinking
• Prototype with Claude Code/Cursor and MagicPattern to build and iterate on the flows and IAs
• Conduct research and validate the solution with customer support
• Contribute to the design system and share AI practice with the team

Staff Product Designer, Payments

Clinical Operations

• Design and build foundations for a variety of 0-1 and scaling initiatives within the Clinical Operations function designed to improve the quality and compliance of services provided at Headway.
• Collaborate cross-functionally to build, execute, monitor, and implement scalable products and processes that enable us to deliver on core business challenges.
• Assess and analyze data to develop and determine strategies for accelerating progress, proactively identify areas for improvement, and deliver on roadmap priorities and team OKRs.
• Build and manage a growing team to achieve these objectives.

Manager, Clinical Operations

Full-stack Engineer

• Building a new mental healthcare system at Headway
• Using technology to build that future
• Making early, foundational architecture decisions that will shape how Headway scales and integrates with payers
• Developing applied LLM systems that deliver actionable, trustworthy feedback to providers
• Tackling the “one-size-fits-none” problem in mental healthcare

Staff Software Engineer, Payer

General Counsel

• Serve as the primary legal advisor to the People team and business leaders on the full range of L&E matters, including hiring practices, performance management, separations, leaves and accommodations, investigations, wage and hour compliance, and other key areas
• Build L&E infrastructure – design and review People-related policies, procedures, and workflows to enhance efficiency and effectiveness
• Be the in-house subject matter expert, training HRBPs and People managers on L&E developments and best-practices
• Draft, review, and negotiate employment-related agreements and documents
• Represent the company, including managing outside counsel, in litigation and related disputes

Senior Counsel, Labor and Employment

Marketing

• Uplevel Our Provider Narrative: Reimagine how we communicate our product value to accelerate adoption of Headway’s full feature stack
• Support Growth & Sales objectives: Structure and prioritize initiatives around equipping them to win
• Own the Provider Go-to-Market experience: Lead end-to-end provider marketing strategy and coordinated GTM efforts
• Strengthen the Provider Community: Evolve our community programs into a competitive moat that fosters connection and fuels loyalty
• Lead a High-Performing Marketing Team: Instill a test-and-learn culture and establish repeatable playbooks

Director, Provider Marketing

• Own our payer contracting strategy, aligning business interests with legal terms and regulations
• Build for scale and implement systems to land high-value payer contracts efficiently
• Review and negotiate the terms of Headway’s health plan agreements
• Partner with outside counsel on cutting-edge approaches to unlock value and mitigate risk

Senior Counsel, Commercial

Human Resources

• Act as a trusted advisor to executives. Anticipate organizational needs, connect people strategy to business outcomes, and challenge assumptions through evidence and insight.
• Lead performance management and talent review processes with rigor and fairness. Coach leaders to recognize and reward top performance, address underperformance, and build high-performing, inclusive teams.
• Partner with leaders to design scalable org structures, strengthen alignment, and enable growth. Use workforce analytics and org design principles to optimize spans, layers, and team health.
• Build trusted relationships with executives and managers, providing candid, actionable feedback that sharpens leadership effectiveness. Reinforce Headway’s cultural principles and managerial excellence through coaching and systems.
• Leverage people data to identify trends, diagnose root causes, and drive measurable improvements in organizational health.
• Lead complex, cross-functional people initiatives end-to-end - from scoping and planning to flawless execution and follow-through. Balance strategic impact with hands-on execution to ensure scalability and continuous improvement.
• Model and amplify Headway’s values and performance standards. Ensure fairness, inclusion, and consistency in decision-making. Surface patterns in sentiment and proactively strengthen engagement and trust.

Director, HR Business Partner – Revenue

Accounting Manager

• Own the operational execution of the revenue accounting function, ensuring accurate, timely, and compliant revenue reporting under ASC 606
• Lead and develop a team of Senior Revenue Accountants, setting clear expectations, coaching for growth, and building a high-performance culture
• Drive the revenue month-end close process, ensuring consistent, timely delivery and continuous improvement in close quality and efficiency
• Serve as a thought partner to the Director of Revenue Accounting by surfacing operational insights, risks, and improvement opportunities that inform the revenue accounting strategy
• Elevate issues, patterns, and opportunities observed in execution into clear, actionable input that informs strategic decisions for the revenue accounting function
• Partner cross-functionally on revenue-impacting initiatives, serving as a key operational lead to ensure alignment and effective delivery
• Oversee the design, implementation, and maintenance of scalable revenue processes, policies, and internal controls
• Identify and drive process improvements through automation, system enhancements, and data-driven insights
• Play a key role in audit readiness and execution for revenue, including reviewing support, resolving issues, and strengthening documentation

Revenue Accounting Manager

Operations

• Drive the build, execution, monitoring & ongoing implementation of scalable products and processes that enable us to deliver on core business challenges
• Leverage your operational expertise to identify opportunities for improved efficiency and automation
• Support and lead cross-functional efforts with our product, engineering, payer, and CX teams to drive core ops processes and achieve team OKRs.

Senior Operations Associate

Revenue Operations

• Support a world class sales team by solving Salesforce cases and meeting our monthly SLA
• Identify key opportunities for efficiencies within our systems
• Learn supported systems including Salesforce, Leandata, Chili Piper, Revenue.io, Attention, among others
• Collaborate with cross-functional partners (Enablement, Data, Engineering, Marketing) and RevOps team members to reduce contact rate
• Learn automations, access controls, reporting, and routing logic in various systems used by the Growth team
• Investigate operational, technical, or process failures to identify underlying causes rather than just treating symptoms

Revenue Operations Associate

Director

• Distill complex clinical processes and language in order to help drive roadmap execution and move product implementation forward
• Shape patient-facing and clinician-facing digital tools
• Lead clinical oversight of AI-enabled features
• Define safety guardrails and quality metrics
• Translate complex clinical workflows into scalable product requirements
• Drive cross-functional alignment across clinical, product, data, and ops

Director, Clinical Product

People Operations

• Manage and mentor the Total Rewards, People Operations, and People Analytics teams, fostering a high-performing, feedback-rich culture that consistently delivers for the business.
• Lead the People Team’s AI strategy, identifying where AI can drive meaningful efficiency and quality gains across Total Rewards, Operations, Analytics, and HRBP workflows, and building the capabilities within the team to leverage these tools responsibly and effectively.
• Architect and scale the People Team tools and systems infrastructure, leveraging AI and best-in-class technology to ensure we are using the most innovative, efficient solutions as we grow. This includes owning our People tech stack strategy — evaluating, rationalizing, and implementing systems that support scale, data integrity, automation, and an exceptional employee experience.
• Build systems and programs that drive Total Rewards excellence, including shepherding critical strategic initiatives such as exploring a transition to a self-funded benefits model in 2026 and strengthening our overall compensation and benefits infrastructure.
• Support the continued evolution of our compensation architecture including scalable leveling frameworks, incentive design, and governance that enable us to hire and retain top-tier talent.
• Partner closely with the executive team on compensation strategy, advising on executive compensation, broad-based adjustments, equity philosophy, and performance-linked reward structures.
• Build and scale a robust People Analytics function, defining the metrics that matter most, strengthening reporting capabilities, and equipping leaders with actionable insights to drive talent decisions.
• Create a best-in-class People Operations engine that sets our HRBPs and business leaders up for success — delivering seamless execution across critical employee moments, from onboarding through promotion, compensation, and lifecycle transitions.
• Define and monitor key People metrics, using data to diagnose gaps, anticipate risk, and design solutions that drive measurable business impact.

Head of Total Rewards, People Ops

Recruitment

• Lead and mentor a team of Business recruiters (GTM + G&A); fostering a culture of excellence
• Partner closely with C-suite and senior leaders across GTM and G&A to design hiring strategies aligned to business priorities, headcount plans, and market realities
• Translate complex hiring goals into milestone-driven execution plans
• Use data to proactively diagnose hiring challenges in close partnership with recruiters
• Elevate sourcing and closing capability across the team, especially in competitive GTM markets with candidates managing multiple offers
• Serve as a trusted advisor to executives, communicating tradeoffs clearly, delivering difficult feedback when needed, and influencing decisions with structured recommendations
• Continuously improve the candidate and hiring manager experience, ensuring Headway’s business hiring process is efficient and aligned with our values