Headway

Business Development Rep

• Drive top-of-funnel pipeline for the Care Partnerships BD team through high-volume cold outbound across phone, email, and LinkedIn
• Book qualified introductory meetings with care management leaders at health systems across the country
• Qualify prospects against the ideal customer profile and ensure clean handoffs to the BD team with full context
• Build and maintain target contact lists across assigned territories
• Collaborate with the manager and BD teammates to refine messaging, targeting, and outreach strategy
• Document and share learnings on personas, objection handling, and conversion performance to strengthen the team's playbook
• Help build a new Business Development Representative function and support health-system partnership growth

Business Development Associate – Care Partnerships

General Counsel

• Serve as a key strategic partner to Procurement, Finance, Customer Experience, and Communications teams
• Own third-party and vendor contracting
• Build and lead agentic first-pass contract review
• Serve as DRI on contract escalations and exceptions
• Own a subset of disputes and escalated requests, including patient cost disputes, escalated provider matters, administrative/regulatory inquiries, and document and records requests
• Partner with Customer Experience and Communications to resolve escalated matters
• Own Headway’s annual corporate insurance cycle and ongoing insurance administration
• Handle other corporate and risk matters in a fast-growing startup environment
• Report to the Associate General Counsel, Commercial and Corporate

Senior Counsel, Corporate – Risk

Infrastructure Engineer

• Architect and own the cloud platform used by every Headway engineer
• Redesign deployment architecture for per-service deploy isolation and functional-area blast-radius containment
• Own the ECS and EKS footprint, evaluate broader EKS adoption for AI workloads, and design inter-service network connectivity
• Own capacity for spiky workloads using predictive floors and early drift detection
• Build a Terraform self-serve infrastructure platform with guardrails
• Enable engineering teams to own standard infrastructure changes while Reliability Engineering reviews non-standard changes
• Establish per-team cost attribution across AWS, Datadog, and LLM spend
• Make infrastructure costs visible and attributable for informed tradeoffs
• Own Python monolith runtime behavior under load, including garbage collection, event loop contention, and runtime limits
• Lead framework and package upgrades
• Drive technical direction and improve other engineers through architecture reviews, runbooks, and paved-road tooling

Senior Software Engineer – Infrastructure

Human Resources

• Lead a team of HR Business Partners
• Serve as a strategic thought partner to the CRO, CCO, CPO, COO, and other business-side executives and leadership teams
• Shape and execute people strategies that enable scale, strengthen leadership, and drive high performance
• Advise on organizational design, performance management, talent planning, and leadership development
• Coach the HR Business Partner team and senior leaders
• Lead performance management and talent review processes
• Design scalable organizational structures and optimize spans, layers, and team health using workforce analytics
• Provide candid, actionable leadership feedback
• Leverage people data to identify trends, diagnose root causes, and improve organizational health
• Lead complex, cross-functional people initiatives from scoping and planning through execution and follow-through
• Model Headway’s values and performance standards
• Strengthen engagement, inclusion, fairness, consistency, and employee trust

Director, HR Business Partner

Clinical Educator

• Evaluate psychiatric providers’ clinical documentation against Headway’s clinical quality standards
• Review initial assessments and progress notes for gaps below evidence-based practice, safe patient care, and rubric standards
• Review clinical decision-making, evidence-based diagnostic criteria, risk assessment, and medication safety
• Complete quality-assessment work including calibration exercises and inter-rater reliability rounds
• Provide asynchronous and live one-to-one remediation support to providers when applicable
• Educate providers using supportive, education-forward feedback tied to documentation expectations, patient safety, and quality standards
• Complete review and documentation work in Headway’s designated systems
• Maintain HIPAA-compliant privacy and confidentiality of patient information

Psychiatric Clinical Quality Peer Educator – Contract

Technical Recruiter

• Run end-to-end design/creative searches from senior individual contributors to Director+ leaders
• Own role scoping, candidate close, candidate quality narrative, funnel health, and search strategy
• Partner with the CPO, VPs of Product and Design, and leadership teams on role definition, leveling, search design, talent bar, market dynamics, and inclusive hiring processes
• Architect structured search plans and diagnose bottlenecks early
• Design and execute targeted sourcing strategies for design and creative talent
• Use data to set funnel expectations and refine search approaches
• Improve design hiring quality and consistency by clarifying competencies, portfolio modules, and structured decision-making
• Build market intelligence on compensation, organizational design, talent pools, and peer-company hiring practices
• Deliver best-in-class candidate experience and executive-level care for senior leaders
• Collaborate with sourcers and coordination partners on seamless searches
• Help Headway scale sustainably and serve providers and patients nationwide

Staff Technical Recruiter, Design

• Run end-to-end product searches across Product Management, Product Design, and Product Analytics/Research
• Own role scoping, candidate close, candidate quality narrative, funnel health, and search strategy
• Partner with the CPO, VPs of Product and Design, and leadership teams on hiring strategy
• Advise on role definition, leveling, search design, talent bar, market dynamics, and inclusive hiring processes
• Architect structured search plans and diagnose bottlenecks
• Design and execute targeted sourcing strategies
• Use data to drive funnel expectations and search decisions
• Improve product hiring quality and consistency
• Clarify product competencies and case exercises
• Build market intelligence on compensation, org design, talent pools, and peer-company hiring practices
• Deliver an exceptional candidate experience for senior product leaders
• Collaborate with sourcers and coordination partners on end-to-end searches

Senior Technical Recruiter, Product

• Run end-to-end product searches from senior individual contributors to Director+ leaders
• Own role scoping, candidate close, and the narrative around candidate quality, funnel health, and search strategy
• Partner with the CPO, VPs of Product and Design, and leadership teams on role definition, leveling, search design, talent bar, market dynamics, and inclusive hiring processes
• Architect structured search plans and diagnose bottlenecks early
• Design and execute targeted sourcing strategies for high-quality product talent
• Use data to set funnel expectations and refine search approaches based on real-time signals
• Improve product hiring quality and consistency by clarifying success profiles, product competencies, and case exercises
• Build market intelligence on product talent, compensation, organizational design, talent pools, and peer-company hiring practices
• Deliver an executive-grade, white-glove candidate experience for senior product leaders
• Collaborate with sourcers and coordination partners on seamless end-to-end searches
• Help Headway scale sustainably and serve providers and patients nationwide

Staff Technical Recruiter – Product

Recruitment

• Run end-to-end marketing searches across the senior individual-contributor pipeline, from role scoping through closing
• Own the narrative around candidate quality, funnel health, and search strategy
• Partner with marketing leadership to define roles, leveling, search design, talent bar, market dynamics, and inclusive hiring processes
• Architect structured search plans, diagnose bottlenecks, set expectations, and provide stakeholder visibility
• Design and execute targeted sourcing strategies for high-quality marketing talent
• Use data to set funnel expectations and refine search approaches based on real-time signals
• Improve hiring quality and consistency by clarifying success profiles, marketing competencies, and case exercises
• Build market intelligence on compensation, organizational design, talent pools, and peer-company hiring practices
• Deliver a best-in-class candidate experience, including executive-level communication and coaching
• Collaborate with sourcers and coordination partners on seamless searches
• Help Headway scale sustainably and serve providers and patients nationwide

Senior Recruiter, Marketing

Accounts Payable

• Lead end-to-end accounts payable operations, including invoice processing, approvals, payments, accruals, and prepaids
• Ensure timely and accurate posting to the general ledger
• Own AP month-end and year-end close procedures, reconciliations, and cut-off controls
• Reduce post-close adjustments and support a clean trial balance
• Prepare, review, and maintain audit-ready PBCs
• Serve as the primary AP subject matter expert for external auditors such as KPMG
• Drive process improvements and automation initiatives to scale AP workflows, reduce manual effort, and strengthen internal controls
• Partner with Corporate Accounting and FP&A on accrual accuracy, cash forecasting, and vendor issue resolution
• Build standardized AP procedures and expectations
• Potentially mentor and manage additional AP resources as the function scales
• Leverage AI tools to streamline workflows, improve accuracy, and increase operational scalability

AP Manager

Director

• Build and lead a recruiting and market intelligence team
• Lead proactive talent mapping, competitive landscape analysis, and sourcing strategy across tech and business functions
• Define market-mapping frameworks covering talent movement, competitors, industries, and schools
• Serve as the sourcing subject matter expert and raise recruiting capability through coaching, enablement, and shared best practices
• Translate market intelligence into actionable sourcing and targeting strategies with recruiting managers and hiring managers
• Build infrastructure and operating rhythm for long-term nurturing of high-potential candidates
• Partner with Talent Brand on events strategy and talent-community touchpoints
• Own data infrastructure and reporting for hiring trends, pipeline health, and market benchmarks
• Define and own campus recruiting strategy, including target schools, events, offer positioning, and conversion
• Build relationships with universities, career centers, and student organizations
• Own event strategy including info sessions, career fairs, hackathons, and diversity-focused programming
• Own the summer internship program from intern hiring through project scoping, onboarding, programming, evaluation, and return-offer decisions
• Partner with HR and Recruiting Programs on return offers, post-offer engagement, and start-date conversion
• Own a defined number of business-wide hires through the team's channels
• Capacity plan with the Head of Recruiting and Recruiting Manager peers
• Connect campus, sourcing, and programs to ensure a seamless candidate experience through hiring and onboarding

Director, Talent Intelligence – Early Careers

Security Engineer

• Partner with Product and Infrastructure teams on secure platforms and infrastructure
• Perform system engineering and implementation efforts
• Conduct security reviews
• Contribute to system design decisions
• Drive continuous improvement of critical infrastructure
• Define and build infrastructure and application guardrails so developers can build securely by default
• Instill a culture of secure system design across engineering
• Build and mature Headway’s cloud security posture across AWS
• Develop AI-native approaches to configuration standards, hardening, and vulnerability remediation
• Assist with incident response, vulnerability management, security reviews, and other security operations

Senior Infrastructure Security Engineer

Business Operations

• Drive complex, cross-functional initiatives that advance pod-level objectives
• Identify opportunities, address dependencies, and ensure stakeholder alignment
• Build and operate scalable workflows and processes from 0→1
• Improve efficiency, reliability, and throughput across the assigned domain
• Use data tools to extract insights and validate assumptions
• Synthesize findings into recommendations guiding pod and organizational priorities
• Plan, execute, and deliver initiatives end-to-end
• Set objectives, timelines, and success metrics
• Drive accountability across functions without formal authority

Business Operations Lead

• Lead high-impact, cross-functional initiatives spanning teams and pods
• Serve as a thought partner to Product, Data, and Operations leaders
• Help shape objectives, influence priorities, and translate complex insights into actionable plans
• Own critical operational workflows
• Design scalable systems
• Mentor team members
• Drive initiatives creating durable, measurable organizational impact
• Design and build foundations for 0-1 initiatives within Business Operations
• Collaborate cross-functionally to build, execute, monitor, and implement scalable products and processes
• Assess and analyze data to develop strategies for accelerating progress
• Proactively identify areas for improvement
• Deliver on roadmap priorities and team OKRs
• Build and manage a growing team

Business Operations Manager

Product Manager

• Own the provider activation funnel and identify activation stages and retention thresholds
• Build strategy to increase activated providers and appointments per new provider
• Drive growth in provider retention and lifetime value
• Partner with sales, CX, pricing, ranking, provider experience, and other teams
• Drive porting tools, flows, and incentives to help providers bring existing patients to Headway
• Develop a segmented onboarding journey for new providers
• Define the team’s strategy, OKRs, and roadmap
• Educate new providers on succeeding with Headway
• Help providers migrate patients onto the platform
• Maximize high-quality appointments during providers’ early tenure