About The Role

As Headway works to build a new mental healthcare system that everyone can access, we’re facing unique operational challenges and opportunities that come with growing and scaling at an unparalleled rate. We’re pushing the boundaries of the existing healthcare system so that we can fulfill our promise to providers, patients, and payers to create access to high quality providers across the nation. In order to do that, we’re building a world class operations team that enables efficiency, growth, and quality, and as a member of this team, you will have the opportunity to have a material impact on the trajectory of Headway and help define a function core to the livelihood of our business and the impact we deliver for our partners and clients.

As a Business Operations Lead, you will drive complex, cross-functional initiatives that advance pod-level objectives. You'll work independently to identify opportunities, address dependencies, and ensure alignment across stakeholders - turning ambiguous problems into structured analyses, scalable processes, and clear recommendations. You'll bring analytical rigor to root-cause investigations, design workflows and tooling that improve efficiency and reliability, and own initiatives end-to-end from scoping through delivery. This role requires strong problem-solving skills, a builder's mindset toward operational design, and the ability to coordinate across teams to drive measurable outcomes.

What you’ll do at Headway

• 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.

You’ll be great for this role if you:

• You have 5-7 years of experience in operational roles at high-growth companies; background in consulting, finance, or business operations preferred but not required.
• You independently deconstruct complex problems into structured, testable components - and you're comfortable working through ambiguity without waiting for full clarity.
• You're proficient with AI & data tools (e.g., Looker, Excel, SQL, dashboards) and use them fluently to extract insights, validate assumptions, and streamline workflows.
• You design systems with scale in mind - anticipating bottlenecks, iterating based on feedback, and codifying learnings into playbooks and standards.
• You coordinate resources and align priorities across teams, building trust through transparency, accountability, and clear communication.
• You take calculated risks and make decisions that advance pod objectives, anticipating downstream impacts before taking action.
• You're motivated by the opportunity to make an impact on one of our generation's defining problems: affordable mental healthcare.

Compensation and Benefits:

The expected base pay range for this position is $105,400 - $155,000 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 Headway works to build a new mental healthcare system that everyone can access, we’re facing unique operational challenges and opportunities that come with growing and scaling at an unparalleled rate. We’re pushing the boundaries of the existing healthcare system so that we can fulfill our promise to providers, patients, and payers to create access to high quality providers across the nation. In order to do that, we’re building a world class operations team that enables efficiency, growth, and quality, and as a member of this team, you will have the opportunity to have a material impact on the trajectory of Headway and help define a function core to the livelihood of our business and the impact we deliver for our partners and clients.

As a Clinical Operations Manager, you will lead high-impact, cross-functional initiatives that span teams and pods. You’ll operate as a thought partner to Clinical, Compliance, Legal, Data, and Operations leaders – helping shape objectives, influence priorities, and translate complex insights into actionable plans. In addition to owning critical operational workflows, you’ll design scalable systems, mentor team members, and drive initiatives that create durable, measurable impact across the organization. This role requires strong judgment, comfort with ambiguity, and the ability to drive alignment and execution across the organization.  

What you’ll do at Headway

• 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.

You’ll be great for this role if you:

• 7+ years of experience in operational roles at high-growth companies, with some background in consulting, healthcare, business operations preferred but not required.
• 2+ years of people management experience; you are a team builder that is passionate about growing and developing talent
• Data is your first-language; you enjoy and are skilled at digging through complex data to solve ambiguous problems.
• You thrive in the unknown, and seek out opportunities to dive into unfamiliar challenges, drive towards outcomes, and shape strategy.
• You are operationally excellent, able to manage a large volume of moving pieces without breaking a sweat.
• You are a collaborator that proactively partners across teams while holding teams accountable for execution.
• You seek an environment that fosters individual growth through open-feedback and high-autonomy.
• You are motivated by the opportunity to make an impact on one of our generation’s defining problems: affordable mental healthcare

Compensation and Benefits:

The expected base pay range for this position is $110,400 - $172,500 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

This is not a traditional EA role.

You'll be a force multiplier to the COO of a category-defining healthcare company — and the architect of how executive support works across the entire organization. In a year, you won't just be running the COO's calendar. You'll have built the function that makes Headway's leadership team operate at its best. 

The Role

We're hiring an Executive Assistant / Head of EA Program to partner directly with Rob Sadow, our Chief Operating Officer, in a high-impact, high-visibility role. You'll own Rob's calendar, commitments, and operating rhythm — ensuring his time and energy are consistently focused on the highest-leverage priorities across a portfolio that spans CX, Operations, Legal, Compliance, Accounting, Finance, and the Executive Team.

But this role goes beyond supporting one executive. Headway is scaling rapidly, and we need someone to define what world-class executive support looks like here — setting the standard, building the team, and ensuring every senior leader at Headway gets exceptional EA support.

What You'll Own

COO Time, Energy & Focus (70%)

• Own the COO's calendar end-to-end — not just scheduling, but making hard prioritization decisions about what gets Rob's time and what doesn't
• Design schedules for deep work, energy, and presence — not just efficiency
• Prep Rob for every meeting with full context on attendees, purpose, relevant documents, and key decisions needed — he should never walk into a meeting cold
• Own travel logistics end-to-end, including events and personal travel
• Manage key relationships on Rob's behalf — knowing who to prioritize, who to push, and when to escalate
• Track action items and commitments across Rob's portfolio so nothing falls through the cracks
• Support personal and family logistics where relevant — including protecting boundaries that matter (like being offline for family time in the evenings)

EA Program & Team (30%)

• Define what exceptional EA performance looks like at Headway — set the operating model, tools, rituals, and standards for the function
• Hire, manage, and coach EAs supporting the CEO and other executives
• Own performance management, career development, and onboarding for the EA team
• Build an EA-specific leveling framework and ensure compensation, expectations, and growth paths are clear and competitive

You'd be a great fit if...

• You are based in the NY area and are excited to be in the office 3-4 days / week
• You have 8+ years of experience supporting C-suite executives at high-growth technology companies — and you genuinely love being an EA. This isn't a stepping stone; it's the career you've chosen and you want to be exceptional at it
• You have experience managing other EAs — hiring, coaching, giving direct feedback, and building a team culture of excellence
• You manage your executive, not the other way around — you're comfortable being vocal, direct, and decisive with a senior leader, and you make independent judgment calls and see three steps ahead
• Your written and verbal communication is flawless — grammar, punctuation, tone, and clarity are non-negotiable. You represent your executive in every interaction
• You build strong relationships cross-functionally — other leaders and EAs trust you, enjoy working with you, and see you as someone who makes things easier, not harder
• You thrive in fast-paced, high-standards environments — Headway operates at an Olympic performance standard, and you're energized by that, not intimidated
• You are excited by our mission to rewire mental healthcare for access and affordability

Compensation and Benefits:

The expected base pay range for this position is $200,000 - $250,000, based on a variety of factors including qualifications and experience. 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

To power this mission, we're building a world-class Operations team that enables efficiency, growth, and quality. As a member of this team, you will have a material impact on the trajectory of Headway and own workflows and processes that are core to the impact we deliver for our patients, providers, and payer partners.

As a Senior Operations Associate, you will operationalize and scale core workflows that will deliver real-world impact to hundreds of thousands of patients and providers around the country. You will be responsible for designing and implementing world-class execution strategy to ensure high-quality operations and you will also be an operational bridge to our product and data teams at Headway in order to drive the future-first nature of the solutions you deliver. 

This role is core to ensuring the operational health of our business and will provide you with deep exposure to the unique mechanics of the healthcare system. This is an opportunity to get hands-on in a data- and product-first environment and own outcomes core to the success of our business. 

• You Will: 
• 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.

• You’d be a great fit if…
• You have 3-5 years of experience in consulting / operations / investment banking or related experience; operations experience at a high-growth startup is a plus.
• You are a self-starter, and are constantly pushing toward clarity and execution.
• You are highly data-driven and can drive complex analyses to identify key actionable insights.
• You are a collaborator who proactively partners across teams while holding others and yourself accountable for business results.
• You are a systems thinker, inclined to solve problems with product and automation.

Compensation and Benefits:

The expected base pay range for this position is $76,160 - $112,000, 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

The patient experience is at the crux of our mission here at Headway to increase affordable access. As the Director, Business Operations for the Patient Group, you will be the "operational spine" for the patient charter responsible for connecting patients to the right care and partnering with them throughout their mental health journey.

You will:

• Drive Strategy through Operational Excellence: You will architect the "operational spine" for the Patient Group, not just running the rhythm, but actively partnering with Product, Engineering, Data, Design and GTM  leads to shape group strategy and translate vision into the roadmaps and execution plans that deliver results.
• Navigate Tradeoffs & Accelerate Growth: You’ll build the frameworks that guide our most critical decisions, from sizing new opportunities to facilitating the high-stakes tradeoff discussions that ensure we are betting on the right strategic levers.
• Partner Deeply with Product & Engineering: You will work shoulder-to-shoulder with Product and Engineering leaders to define priorities, shape roadmaps, and drive execution against the highest-impact opportunities. 
• Serve as the Connective Tissue: You’ll be the vital link between the group and cross-functional stakeholders. Beyond just reporting  progress, you know how to bring the right people together to solve complex problems, ensuring work is tied to measurable impact and that all dependencies are aligned across the organization.
• Build a High-Impact Team: You will lead and mentor a lean Business Operations team dedicated to scaling our patient acquisition, overseeing the operational strategy for our core experience, growth initiatives, and strategic partnerships.

You’d be a great fit if:

• Have 10+ years of experience in Business Operations or Strategy & Operations in growth-focused roles
• Have 5+ years of experience managing high-performing teams.
• Are a strategic operator, moving effortlessly between architecting long-term strategies and diving into the granular models and metrics required to hit today’s goals.

Have deep product and data intuition, with the ability to define product strategy and performance metrics that drive innovation.

• Have led high-stakes, cross-functional processes, aligning senior stakeholders around priorities, tradeoffs, and timelines, especially in ambiguous or rapidly changing environments.
• Excel at synthesizing messy inputs into clear, compelling narratives that inform high-level decisions around resourcing, strategy, and organizational design.
• Act as a strategic orchestrator, identifying cross-functional dependencies and proactively bringing the right people together to unblock projects and ensure progress results in company-wide success.
• Care deeply about delivering meaningful impact — for providers, patients, and Headway’s mission.

Compensation and Benefits:

The expected base pay range for this position is $169,600-$265,000, 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 Headway works to build a new mental healthcare system that everyone can access, we’re facing unique operational challenges and opportunities that come with growing and scaling at an unparalleled rate. We’re pushing the boundaries of the existing healthcare system so that we can fulfill our promise to providers, patients, and payers to create access to high quality providers across the nation. In order to do that, we’re building a world class operations team that enables efficiency, growth, and quality, and as a member of this team, you will have the opportunity to have a material impact on the trajectory of Headway and help define a function core to the livelihood of our business and the impact we deliver for our partners and clients.

As a Business Operations Manager, you will lead high-impact, cross-functional initiatives that span teams and pods. You’ll operate as a thought partner to Product, Data, and Operations leaders – helping shape objectives, influence priorities, and translate complex insights into actionable plans. In addition to owning critical operational workflows, you’ll design scalable systems, mentor team members, and drive initiatives that create durable, measurable impact across the organization. This role requires strong judgment, comfort with ambiguity, and the ability to drive alignment and execution across the organization.  

What you’ll do at Headway

• Design and build foundations for a variety of 0-1 initiatives within the Operations function.
• 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.

You’ll be great for this role if you:

• Have 7+ years of experience in operational roles at high-growth companies, with some background in consulting, finance, or business operations preferred but not required
• Have 2+ years of people management experience; you are a team builder that is passionate about growing and developing talent
• Use data as your first-language; you enjoy and are skilled at digging through complex data to solve ambiguous problems.
• Thrive in the unknown, and seek out opportunities to dive into unfamiliar challenges, drive towards outcomes, and shape strategy
• Are operationally excellent, able to manage a large volume of moving pieces without breaking a sweat
• Are a collaborator that proactively partners across teams while holding teams accountable for business results
• Seek an environment that fosters individual growth through open-feedback and high-autonomy
• Are motivated by the opportunity to make an impact on one of our generation’s defining problems: affordable mental healthcare

Compensation and Benefits:

The expected base pay range for this position is $121,600 - $190,000 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