Headway

Backend Engineer

• The Revenue Engine Team is making the foundational platform decisions that will shape how Headway moves money — between patients, providers, and payers — at the scale our growing network demands. As one of two staff engineers in the group, you'll partner with engineering leadership to set technical direction across our Payment Platform and Clearinghouse Platform teams.
• This is platform work in the truest sense. Every payment that's charged or paid out, every claim that's filed and reconciled, every dollar that flows through Headway depends on the systems your teams own. As Headway's network grows — more patients, more providers, more payers, more transaction volume — the reliability, throughput, and correctness of these systems become the difference between a business that scales and one that doesn't.
• You'll lead the design of fault-tolerant, observable, and deeply reconciled integrations with the third-party services we depend on. You'll build the abstractions and standards that let dozens of adjacent engineering teams — Billing Infrastructure, Patient Billing, Provider Payouts, and others — ship faster and more safely on top of our platform.
• And you'll do it as a hands-on technical leader: writing code where leverage is highest, mentoring senior engineers across both pods, and shaping the operational excellence that this domain demands.
• This role is for engineers who get energized by distributed systems problems with real consequences — concurrency, idempotency, partial failures, all with a substantial potential blast radius — and who want to apply that craft to a mission that actually matters: building a mental healthcare system that everyone can access.

Staff Backend Software Engineer – Revenue Engine

Medical Billing and Coding

• Audit behavioral health documentation and coding (ICD-10-CM and CPT) for accuracy, compliance, and completeness
• Deliver actionable feedback to providers through 1:1 remediation meetings, educating on coding and documentation guidelines (i.e., coding based on medical decision making (MDM) for outpatient Evaluation and Management services)
• Serve as a subject matter expert by answering coding-related questions to support internal teams and create processes
• Contribute to provider education efforts, including drafting content, identifying documentation gaps, and advising on clinical documentation standards
• Provide insights on coding trends, identify risk areas, and recommend improvements to tooling, product, and training
• Collaborate with cross-functional partners on initiatives and enhancements regarding billing code guardrails
• Stay current with evolving coding guidelines, payer rules, and industry standards through continuing education and independent learning

Senior Medical Coding Specialist

Medical Director

• Support Headway health plan partnerships and strategy
• Promote external relations with Payers through presentations and sales meetings
• Drive innovative data analyses to prove patient outcomes and generate insights
• Develop understanding of digital tools for mental health clinicians
• Collaborate with cross-functional teams including product, design, and operations
• Be willing to travel

Associate Medical Director – Payer Partnerships

QA Engineer

• Own a defined area of the QA program end-to-end (calibration and rubric governance, AI-powered analytics, or partner quality) and drive it from signal to action
• Set quality standards and rubric logic for your area; ensure consistent application across channels and partners and recommend framework updates based on outcomes
• Configure and continuously improve AI-QA tooling (ObserveAI or similar) with set scoring logic, monitoring accuracy, and ensuring the platform delivers consistent, actionable output
• Build automation into QA workflows to reduce manual overhead and expand coverage; establish AI-assisted processes for status updates, reporting, and initiative recaps
• Analyze quality and conversation data to surface DSAT drivers, behavioral trends, escalation patterns, and workflow gaps by going beyond what happened to understand why
• Design and maintain dashboards that track key quality metrics; translate findings into clear operational recommendations for CX leadership
• Produce structured insight reports (clear signal, root cause, recommended action) and ensure findings flow into training, content, coaching, and product decisions
• Contribute QA input to WBR/MBR cycles and cross-functional planning; give leadership consistent visibility into program health and customer experience impact
• Partner with BPO teams and CX stakeholders to align on standards, drive calibration, and keep expectations consistent across every channel and partner
• Collaborate with Enablement, Knowledge, and Programs to ensure quality signals drive decisions across training, content, and coaching and deliver initiatives that measurably improve agent quality and customer satisfaction

Quality Assurance Lead

Program Manager

• Design and run AI adoption programs that enable the TA team to effectively use AI in their workflows
• Build and manage TA enablement programs: Recruiter skill development, tooling onboarding, and process documentation that scales with a high-volume, fast-paced hiring environment
• Own hiring manager and interviewer enablement end-to-end
• Define success metrics for every program you own; building dashboards that make enablement ROI visible
• Partner cross-functionally to connect TA programs to the broader company strategy

Program Manager, Talent & AI Enablement

Product Manager

• Define the vision and strategy for Headway's CX product — spanning AI-powered resolution, agent tooling, proactive engagement, channel strategy, knowledge systems, and the feedback loops that connect support insights back to the product.
• Build and lead a team of product managers focused on reducing cost-to-serve while increasing resolution quality and customer satisfaction.
• Own the AI resolution layer — build the agentic workflows and API integrations that enable the AI agent to actually resolve problems, not just answer questions. Define the autonomy framework: what AI handles without human involvement, what needs guardrails, and what requires a human.
• Build proactive engagement — systems that contact customers before they discover problems. Shift Headway's CX from reactive to proactive.
• Launch and unify all contact channels — email, text, and voice — with intelligent routing that delivers differentiated experiences based on customer context, value, and issue type.
• Own the knowledge and quality layer — machine-readable SOPs, AI evaluation frameworks and crisis escalation pathways.
• Partner deeply with CX Operations to build agent tooling that makes human agents dramatically more effective — AI copilot, full journey context, auto-generated summaries.
• Close the feedback loop: build the system that identifies the highest-impact product defects driving support volume and surfaces them to insurance platform teams for upstream fixes.
• Establish measurement frameworks that connect CX product investments to business outcomes..

Director of Product, CX Product

Business Operations

• Drive complex, cross-functional initiatives that advance pod-level objectives - identifying opportunities, addressing dependencies, and ensuring alignment across stakeholders.
• Build and operate scalable workflows and processes (0→1) that improve efficiency, reliability, and throughput across your domain.
• Leverage data tools to extract insights, validate assumptions, and inform decisions, synthesizing findings into clear recommendations that guide pod and organizational priorities.
• Plan, execute, and deliver initiatives end-to-end by setting clear objectives, timelines, and success metrics – driving accountability across functions without formal authority.

Business Operations Lead

Recruitment

• Schedule and coordinate interviews end-to-end across a portfolio of open roles, ensuring every detail is confirmed and nothing falls through the cracks
• Serve as a primary scheduling point of contact for candidates throughout the interview process, delivering a warm and organized experience
• Maintain accurate candidate records and pipeline data in Greenhouse in real time
• Partner with recruiters and sourcers to manage logistics — calendar coordination, interviewer prep, and video link setup — across multiple simultaneous reqs
• Communicate proactively when schedules change, conflicts arise, or candidates need updates
• Support TA operational workflows, including BrightHire coordination and other tooling as we automate and streamline

Recruiting Coordinator

• Own interview scheduling end-to-end for all active senior level searches - managing complex, multi-timezone calendars across senior candidates, executives, and cross-functional interview panels
• Serve as the primary coordination point of contact for executive candidates, delivering a warm, polished, and organized experience at every touchpoint
• Maintain real-time accuracy in Greenhouse across all exec pipelines - candidate records, interview stages, and pipeline data
• Build and own the operational playbook for executive coordination - confirmation cadences, prep material delivery, debrief logistics, to ensure the process is consistent and scalable
• Partner closely with senior recruiters to proactively flag scheduling risks, resolve conflicts, and keep searches moving without interruption
• Handle sensitive search details with discretion, representing Headway professionally in every interaction with candidates and hiring leaders

Executive Recruiting Coordinator

Growth Marketing

• Own paid acquisition (Search, Social, OLV/OTT, Programmatic/Display), Lifecycle (email/SMS/push), and Organic (SEO, content distribution, Reddit/IG/TikTok/YouTube).
• Lead channel plumbing, experimentation frameworks, attribution, incrementality, MMM, and reporting — co-owning approach with Eng and Data but owning the outcomes.
• Drive briefing, testing velocity, and learning loops across message × audience × asset × surface.
• Align patient and provider growth to prevent channel overlap and unlock network effects.
• Hire, lead, and develop a high-bar, technical, and creative team across paid, lifecycle, and organic.
• Work with Product/Eng to build surfaces that drive conversion and quality, not just spend.

Head of Patient Growth – Marketing

People Operations

• Design strategic People Systems suite, including Workday optimizations in partnership with our People Systems' Engineer
• Improve technology to scale Headway's lifecycle operations to provide efficient support and automations for the employee lifecycle, and the internal People team
• Manage and develop a team of People systems and operations professionals, fostering a culture of continuous improvement and excellence
• Partner cross-functionally (IT, People Partners, etc) to visualize and plan system integrations and workflows intuitively and securely
• Scope roadmaps and timelines focused on simplicity, efficiency, and the strategic adoption of AI tools
• Develop and lead Change Adoption programs, including creating training resources to ensure clarity for all staff
• Evaluate service delivery success, maintaining benchmarks for resolution and response times
• Continuously iterate and improve People team workflows
• Assess, recommend, and implement new tools and platforms as Headway grows

Senior Manager, People Systems & Operations

Analyst

• Architect the Capacity Engine by building and maintaining a comprehensive capacity model
• Model Agent Productivity by transforming raw agent-level workforce data
• Own the Financial Translation by bridging Operations and Finance
• Drive BPO Capacity Locks by generating and enforcing headcount lock plans
• Own the Staffing Plan by computing and projecting operational rates
• Translate Messy Reality into Clean Data by mapping raw ticket data

Capacity Planning Analyst

Manager

• Own Headway's SEM program end-to-end: campaign architecture, keyword strategy, bidding, budget allocation, and performance optimization across Google Ads and Microsoft Ads.
• Scale SEM spend efficiently: grow budgets toward $50M+ annually while maintaining target CAC and ROAS.
• Build incrementality measurement: design and run geo-lift studies, holdout tests, and brand/non-brand incrementality analysis.
• Optimize the full funnel: partner with Product and Engineering to improve post-click conversion from landing page through booked appointment.
• Partner directly with Engineering and Data Science: own tracking implementation, attribution infrastructure, and performance reporting.
• Leverage AI tools: Build and run AI agents in Claude Code that automate keyword expansion, ad copy generation, bid optimization signals, and competitive intelligence.

Channel Manager – SEM

Account Manager

• Own and drive mid-market health system opportunities from first touch through launch
• Build relationships with Director+ care management, population health, and clinical operations leaders
• Run outbound and manage inbound leads across your assigned states
• Develop account strategies that consider long-term adoption, not just short-term wins
• Support Associate Principals with research, prep, and account coverage on enterprise opportunities
• Collaborate cross-functionally with Partner Success, Product, and Operations to ensure successful launches

Business Development Lead, Care Partnerships

• Be responsible for the happiness of our care partners and clinicians
• Create new strategies to engage with clinicians that refer to Headway
• Support the team in preparing for executive meetings with partners
• Build and grow relationships with care partners’ (health systems, medical clinics, and other strategic partners) teams and leadership
• Leverage data to generate insights and identify new opportunities for partnership growth
• Collaborate with cross functional, internal stakeholders to deliver insights to inform product and operations strategy