About the Role

The Recruiting Coordination team is the operational backbone of Headway's talent engine. We're the team that makes hiring happen — from the moment a candidate is scheduled for their first interview to the day an offer is signed. We own the logistics, the details, and the candidate experience that shapes how people feel about Headway before they ever join.

We are looking for a strong partner for our Recruiters and Sourcers to enable an exceptional candidate experience for potential hires across the company. As we continue to scale at hyper-growth pace, we're seeking an operationally excellent and relationship-driven teammate to plug into searches, collaborating effectively with hiring managers, candidates, interview teams, and talent stakeholders. This is a great opportunity for a Talent professional who is looking for exposure to a mission-driven, high growth organization!

You Will

• 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

You'd Be a Great Fit If…

• You're known for being organized and detail-oriented — you're the person who catches the timezone error before it becomes a problem
• You've worked in a high-volume coordination, scheduling, or operations role and thrived under the load
• You communicate clearly and warmly — candidates and interviewers alike feel informed and taken care of
• You treat data hygiene as a professional standard, not an afterthought
• You're proactive — you don't wait to be asked before flagging a conflict or closing a loop
• You're energized by the pace of a fast-growing company and comfortable with change

Compensation and Benefits:

The expected base pay range for this position is $91,000-$119,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

We're hiring an Executive Recruiting Coordinator to own the candidate experience end-to-end across all of our senior and executive level searches. In this role, you will operate as a strategic partner to our Executive Recruiters and Leadership team, ensuring candidates feel taken care of and have a truly remarkable experience interviewing with Headway. You’ll own complex scheduling across multiple senior stakeholders, manage high-touch candidate logistics and ensure we are providing a ‘white glove’ experience every time. 

You Will

• 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

You'd Be a Great Fit If…

• You have 2+ years coordinating executive or senior leadership searches before and understand what makes the candidate experience at that level different
• Your scheduling record is near-perfect - you're the person who catches the timezone error, the double-booking, and the missing confirmation before anyone else notices
• You can independently own a full portfolio of complex searches without daily direction - you know what needs to happen and you make it happen
• You communicate with polish and precision - your emails to VP and C-suite candidates are clear, warm, and professional without being stiff
• You think in systems - when something's inefficient, you don't just work around it, you fix it and document it so it doesn't happen again
• You handle ambiguity and last-minute changes without losing your footing — executive schedules shift constantly, and you stay ahead of it

Compensation and Benefits:

The expected base pay range for this position is $124,000-$146,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

As a Senior Manager, HR Business Partner at Headway, you will serve as a strategic thought partner to our R+D executives. You’ll shape and execute people strategies that enable scale, strengthen leadership, and drive Olympic-level performance. Partnering closely with our leaders, you’ll provide counsel on organizational design, performance management, talent planning, and leadership development - balancing near-term priorities with long-term organizational health and cultural integrity. You’ll use data-driven insights and sound judgment to identify trends, influence decisions, and lead high-impact initiatives that elevate the employee experience, strengthen manager capability, and ensure our teams are empowered to perform at their best.

What You’ll Do

• Strategic Business Partnership: Act as a trusted advisor to executives. Anticipate organizational needs, connect people strategy to business outcomes, and challenge assumptions through evidence and insight.
• Talent Strategy & Performance: 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.
• Organizational Design & Effectiveness: 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.
• Leadership Coaching & Influence: 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.
• Analytical & Data-Driven Decision Making: Leverage people data to identify trends, diagnose root causes, and drive measurable improvements in organizational health.
• Project Management & Operational Excellence: 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.
• Cultural Stewardship & Employee Experience: 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.

You’d Be a Great Fit If You...

• Have 12+ years of progressive experience in HR or HR-adjacent roles (e.g., Chief of Staff, Strategy), with a track record of supporting senior executives in high-growth or scaling environments.
• Are a strategic operator who can anticipate organizational needs, shape people strategies, and influence through credibility and insight.
• Are data-driven, using qualitative and quantitative insights to inform decision-making, program design, and measurement of impact.
• Are a trusted coach and advisor, capable of balancing candor and empathy while influencing at all levels.
• Have deep expertise in org design, performance management, and leadership development.
• Thrive in fast-paced, high-growth settings where agility, sound judgment, and ownership are essential.
• Model Headway’s cultural principles and uphold our Olympic-level performance standard, driving clarity, accountability, and continuous improvement.

Compensation and Benefits:

The expected base pay range for this position is $180,000 - $250,000, based on a variety of factors including qualifications, experience, and geographic location. 

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the Role

Headway is looking for a Senior Manager, People Systems & Operations to join the People team to lead our HR technology strategy and operations. You will work closely with the Director of Total Rewards and People Operations to build and optimize a scalable People technology ecosystem that supports Headway's growth. This is a unique opportunity to lead a team in managing our systems while enhancing the daily service experience for all Headway employees.

We're looking for a people leader with deep expertise in People Systems and Operations, including technical Workday administration skills, who is proactive and able to thrive in a high-growth environment. You will be critical to ensuring our People initiatives are supported by robust, high-performing systems that leverage emerging technologies and automation.

You Will

• Design strategic People Systems suite, including Workday optimizations in partnership with our People Systems' Engineer
• Improve technology in order to scale Headway's lifecycle operations to provide efficient support and automations for the employee lifecycle, as well as 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
• For all systems workflows and programs, whether creating new or optimizing legacy processes:
• Scope roadmaps and timelines focused on simplicity, efficiency, and the strategic adoption of AI tools
• Develop and lead Change Adoption programs, including the creation of 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

You'd Be a Great Fit If…

• You have 10+ years of experience in People Operations and Systems with at least 5 years specifically focused on Workday administration
• You have a track record of managing and developing a team of People professionals
• You are deeply knowledgeable and adept in Workday (HCM, Advanced Compensation, Absence & Time Tracking) and other People systems (examples: Google Workspace, CultureAmp, Greenhouse, Glean)
• You are a strategic thinker who can map out a multi-year roadmap while also executing tactical configurations and integrations
• You are highly organized and have a proven track record of managing highly complex, cross-functional projects with diverse stakeholders
• You function well in a high-paced environment, having experience managing workflows for thousands of employees and handling rapid scaling
• You're skilled in technical support and enablement, capable of training staff on new platforms and building internal knowledge centers
• You collaborate and build credibility across the organization through strong communication

Compensation and Benefits:

The expected base pay range for this position is $169,000-$212,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

About the role:

Headway is hiring a Director of Technical Recruiting to lead and scale R&D hiring across Engineering, Data, Product, Design, Security, and IT. As the most senior leader overseeing technical recruiting, you will set the strategy, design the operating model, and deliver on a mission-critical hiring engine that fuels Headway’s growth.

You will lead and develop a high-performing team of senior recruiters and managers while partnering closely with leaders across R&D. The systems you build and the talent you bring in will directly impact Headway’s ability to serve providers and patients at scale.

In this role, you’ll blend people leadership, operational excellence, and strategic influence to build an Olympic-level recruiting team.

You will:

• Partner with leaders across technical teams to scale their departments, advising on search strategies and providing tailored, scalable solutions
• Leverage metrics to diagnose gaps and proactively provide solutions, keeping a strong pulse on tech hiring trends and the impact it has on your funnels
• Manage a team of senior recruiters and managers with a focus on performance and career growth, embracing Headway’s F.U.E.L. culture (Feedback Uplifts Every Level)
• Serve as a trusted advisor to senior executives, building strong relationships
• Deliver exceptional hiring outcomes by focusing teams on the highest-impact priorities, removing obstacles early, and aligning with cross functional teams
• Drive operational excellence by setting the standards and rhythms that enable a high-performing, high-velocity recruiting team
• Shape long-range R&D talent strategy and partner with executives on headcount planning and capacity modeling
• Influence the systems and tooling that underpin all tech hiring that will allow the TA team to work efficiently and effectively
• Strengthen Headway’s tech talent brand by ensuring an exceptional, consistent candidate experience across every touchpoint

You’d be a great fit if…

• Bring 7+ years of recruiting leadership experience, including managing managers and senior recruiters in high-growth, tech-enabled environments
• Have a track record of scaling technical organizations, building diverse and inclusive teams, and maintaining a high talent bar
• Operate as a business partner to senior leaders, grounding strategies and recommendations in data and market insights
• Operate as a first-principles thinker, grounding your decisions in data, disentangling root issues in the funnel, and crafting scalable TA solutions that accelerate hiring
• Navigate ambiguity with structure and speed
• Communicate with clarity and executive presence, tailoring your message to different audiences and influencing decisions through structured, compelling storytelling
• Demonstrate a bias for operational excellence, continually improving how the team works and removing friction for candidates, recruiters, and stakeholders

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
  • Equity compensation
  • Medical, Dental, and Vision coverage
  • HSA / FSA
  • 401K
  • Work-from-Home Stipend
  • Therapy Reimbursement
  • 16-week parental leave for eligible employees
  • Carrot Fertility annual reimbursement and membership
  • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development

#LI-hybrid