As a Strategic Finance Manager, you will sit within the Strategic Finance GTM team and play a critical role in driving durable marketplace health across Provider and Patient. This is a highly cross-functional role for someone who thrives at the intersection of financial analysis and strategic decision-making. You'll build models, track performance, and surface insights that drive appointment volume, retention, and long-run unit economics.

You will:

• Serve as the primary Finance Business Partner for appointments reporting — patient churn, provider churn, appointments per provider, net revenue retention, and active patient behavior
• Build and maintain functional operating models for Provider and Patient, and drive ongoing budgeting and forecasting processes for the function
• Lead deep dives to identify business problems, perform root cause analysis, and develop strategies for accelerating progress — monitoring trends, surfacing early signals of de-averaged performance, and partnering with product, operating, and growth teams to address issues and scale successful behaviors
• Partner cross-functionally to surface insights and support strategic decision-making
• Develop dashboards, reporting, and executive-ready materials to communicate progress against goals

You’d be a great fit if:

• You have 6+ years of professional experience, ideally in a mix of financial services (Investment Banking / Consulting / Private Equity) and highly analytical roles at a fast-growing tech company (Strategic Finance)
• You are highly proficient in Google Sheets (advanced formulas) and Looker (or similar BI tools) and comfortable working with large datasets
• You are detail-oriented and have a “measure twice, cut once” approach when working with financial data
• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making
• You’re excited to work cross functionally with the business teams to develop a greater understanding of function-specific efficiency metrics and help course-correct where necessary
• You take ownership and are a resourceful self-starter—you proactively seek context, solve ambiguous problems, and anticipate stakeholder needs
• You communicate complex insights clearly, tailoring your message for different audiences (finance vs. business/product partners)
• You thrive in a fast-paced, cross-functional environment and enjoy collaborating with Provider, Patient, product, and growth teams
• You are excited about joining a mission-driven company and driving marketplace efficiency and durable growth to improve mental healthcare access

Compensation and Benefits:

The expected base pay range for this position is $152,000 - $190,000, 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

#LI-LN1

As a Strategic Finance Lead, GTM, you will sit within the Strategic Finance team and play a critical role in ensuring capital is deployed efficiently across Provider and Patient Growth initiatives. This is a highly cross-functional role for someone who thrives at the intersection of financial analysis and strategic decision-making. You'll build models, track performance, and surface insights that guide how we allocate resources and scale our GTM investments.

You Will

• Build and maintain financial models to assess GTM investment efficiency, scenario plan, and evaluate trade-offs across growth initiatives
• Own budgeting and forecasting processes for GTM spend, partnering with budget owners to align plans with strategic priorities.
• Analyze operating KPIs and funnel data to evaluate unit economics, channel performance, and overall GTM effectiveness
• Partner cross-functionally to surface insights and support strategic decision-making
• Develop dashboards, reporting, and executive-ready materials to communicate progress against goals

You’d be a great fit if…

• You have 4+ years of professional experience, ideally in a mix of financial services (Consulting / Equity Research / Private Equity) and highly analytical roles at a fast-growing company (Strategic Finance)
• You are highly proficient in Google Sheets (advanced formulas) and Looker (or similar BI tools) and comfortable working with large datasets
• You are detail-oriented and have a “measure twice, cut once” approach when working with financial data
• You’re excited to work cross functionally with the business teams to develop a greater understanding of function-specific efficiency metrics and help course-correct where necessary
• You take ownership and are a resourceful self-starter—you proactively seek context, solve ambiguous problems, and anticipate stakeholder needs
• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making
• You communicate complex insights clearly, tailoring your message for different audiences (finance vs. marketing)
• You thrive in a fast-paced, cross-functional environment and enjoy collaborating with marketing, finance, and growth teams
• You are excited about joining a mission-driven company and driving marketing efficiency to improve mental healthcare access

Compensation and Benefits:

The expected base pay range for this position is $131,750 - $165,000, 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

#LI-LN1

As a Senior Revenue Accountant, you will play a key role in ensuring accurate and compliant revenue accounting for a fast-growing company. You’ll focus on ASC 606 revenue recognition, month-end close, reporting, and building scalable processes and systems. This role is highly cross-functional, partnering with Finance, Legal, Data, Product, and Engineering teams to ensure revenue is reported accurately and efficiently. This role offers an opportunity to apply creative thinking and strong problem-solving skills to make a lasting impact on Headway’s growth and operations.

You will:

• 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

You’ll be great for this role if:

• You have 3+ years of accounting and/or audit experience
• You have a Bachelor’s degree in Accounting or another relevant field
• You are a CPA (or CPA track)
• You have strong working knowledge of ASC 606 (a plus, but not required)
• You have a Big 4 audit background and/or experience in high-growth environments
• You have strong communication skills and the ability to collaborate effectively across teams
• You are a problem solver and can work efficiently under pressure
• You take initiative and enjoy tackling complex accounting and business challenges

Compensation and Benefits:

The expected base pay range for this position is $95,200- $140,000, 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

As Headway’s Director of FP&A, you will build and manage a high-performing team overseeing corporate finance activities, operationalize KPIs to provide insight into business performance and develop best practices to ensure timely visibility into company performance. You will partner with cross-functional teams to understand performance, identify areas of opportunity, and support strategic decision-making. You will be a key player in driving coordination of strategic and financial planning processes as we scale. You will also serve as a trusted advisor and critical business partner to G&A functional leaders across the organization. This is an exciting opportunity for an experienced, detail-oriented leader who wants to make a significant impact on Headway’s growth and success.

You will: 

• Establish and drive financial planning processes, ensuring resource allocation stays within budget and forecasts are tightly linked to the company’s strategic goals
• Oversee the company-wide operating model, ensuring key inputs are linked to company growth and profitability for use in annual planning/budgeting and monthly forecasting
• Perform robust financial analysis on financial results and operating KPIs, identifying underlying trends and areas of opportunity
• Design and deliver monthly/quarterly reporting packages that tell the story behind the numbers for the exec team and Board
• Optimize systems to ensure automation of critical processes as we scale
• Support competitive intelligence, M&A and other corporate development initiatives
• Hire and develop a high-performing FP&A team to support the needs of the business
• Drive capital allocation strategy, cash management, and expense governance
• Support investor reporting, due diligence, and board-level discussions

You’d be a great fit if:

• You have 10-15+ years of strategic finance/FP&A experience at a high-growth startup, ideally including 2+ years of consulting/banking/investing
• You understand that people drive change, not spreadsheets, and are passionate about working with partners across all levels of the organization to steer progress
• You have exceptional analytical skills with the ability to drill down into the weeds while maintaining a strategic lens
• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making
• You have strong financial acumen and expertise in building financial models to support multiple business needs
• You are a curious self-starter, resourceful and have a knack for problem-solving
• You are a natural leader who enjoys hiring, mentoring and managing people to reach their highest potential 
• You’re energized by joining an early-stage startup and making immediate impact in a high-growth environment 
• You are an excellent communicator with strong interpersonal skills

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.

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-LN1

As Headway’s Senior Manager, FP&A, you will be at the center of the financial processes that drive operational excellence and keep our business moving forward while holding accountability. You will support the overall corporate finance function through the cadence of monthly reporting, forecasting and exec-level KPI reviews. You will serve as a critical business partner to G&A functional leaders across the organization, and identify areas of opportunity while supporting strategic decision-making. This is an exciting opportunity for an experienced, detail-oriented leader who wants to make a significant impact on Headway’s growth and success.

You will: 

• Drive financial planning processes, ensuring the company resource allocation stays within budget and forecasts are tightly linked to the company’s strategic goals
• Support and evolve the company-wide operating model, ensuring key inputs are linked to company growth and profitability and the model is a reliable foundation for forecasting and planning
• Perform robust financial analysis on financial results and operating KPIs, identifying underlying trends and areas of opportunity
• Build and deliver monthly/quarterly reporting packages that tell the story behind the numbers for the exec team and Board
• Leverage tooling/systems to ensure automation of critical processes as we scale
• Support competitive intelligence, M&A and other corporate development initiatives
• Support investor reporting, due diligence, and board-level discussions

You’d be a great fit if:

• You have 8-10+ years of strategic finance/FP&A experience at a high-growth startup, ideally including 2+ years of consulting/banking/investing
• You understand that people drive change, not spreadsheets, and are passionate about working with partners across all levels of the organization to steer progress
• You have exceptional analytical skills with the ability to drill down into the weeds while maintaining a strategic lens
• You have strong financial acumen and expertise in building financial models to support multiple business needs
• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making
• You are a curious self-starter, resourceful and have a knack for problem-solving
• You’re energized by joining an early-stage startup and making immediate impact in a high-growth environment 
• You are an excellent communicator with strong interpersonal skills

Compensation and Benefits:

The expected base pay range for this position is $144,000 - $225,000 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

#LI-LN1

About the role:
Headway is seeking an AP Manager to own the accounts payable function and build scalable, efficient processes that support accurate financial reporting and audit readiness. In this role, you’ll manage AP operations, month-end close, reconciliations, and audit support while partnering cross-functionally to optimize workflows and vendor management. This is a great opportunity for a hands-on, detail-oriented individual to drive accuracy, efficiency, and scalability across the AP function. 

You will:

• Lead end-to-end AP operations including invoice processing, approvals, payments, accruals, and prepaids to ensure timely and accurate posting to the GL.
• Own month-end and year-end close procedures for AP, including reconciliations and cut-off controls, reducing post-close adjustments and supporting a clean trial balance.
• Prepare, review, and maintain audit-ready PBCs and 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 to support accrual accuracy, cash forecasting, and timely resolution of vendor issues.
• Build standardized AP procedures and expectations, with future opportunity to mentor and manage additional AP resources as the function scales.
• Enhance automation and process efficiency by leveraging AI tools to streamline workflows, reduce manual effort, and improve accuracy and scalability across operations

You’d be a great fit if:

• You have 6+ years of accounting experience with 3+ years managing AP operations in a high-growth or complex environment (healthcare, fintech, or SaaS preferred).
• Proven experience with month-end/year-end close, reconciliations, and audit support.
• Strong knowledge of AP-related US GAAP (expense recognition, accruals, prepaids) and internal controls.
• Hands-on operator who can implement scalable processes and drive automation initiatives.
• Excellent communicator with strong interpersonal skills, able to collaborate with cross-functional partners and vendors.
• Passionate about building reliable, efficient AP processes and developing team capabilities.
• Hands-on experience with NetSuite and Ramp, with the ability to optimize workflows and reporting within these systems.
• A curiosity into using AI tools and a dedication to leveraging AI for process automation and efficiency.

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. 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

Headway is seeking a Manager, Revenue Accounting to help lead and scale the revenue accounting function. In this role, you will translate the revenue accounting strategy set by the Director of Revenue Accounting into a best-in-class operating model. You will own the day-to-day execution of revenue accounting, lead and develop a team of Senior Revenue Accountants, and drive continuous improvements across processes, systems, and controls.

This is a highly cross-functional role partnering with Finance, Legal, Data, Engineering, Product, and Operations on revenue-impacting initiatives. This role offers the opportunity to have a meaningful impact on how revenue is accounted for, reported, and scaled at Headway.

You will:

• 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
• Drive the adoption of AI and automation across revenue accounting processes to improve scalability, accuracy, and efficiency
• Play a key role in audit readiness and execution for revenue, including reviewing support, resolving issues, and strengthening documentation

You’d be a great fit for this role if:

• You have 5-7+ years of accounting experience, including significant experience in revenue accounting at high-growth companies
• You have 2-3+ years of experience managing or leading others, with a demonstrated ability to develop talent and drive results through teams
• Strong working knowledge of ASC 606, with hands-on experience applying revenue guidance in practice
• You have experience operating in fast-paced, cross-functional environments with evolving systems and processes
• You are both highly detail-oriented and comfortable operating at a higher level, connecting execution to business outcomes
• You are an excellent communicator who can translate complex accounting topics for non-accounting partners
• You bring a builder mindset and enjoy creating structure, clarity, and scalable solutions
• You are a CPA with Big 4 and/or high-growth company experience

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. 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

#LI-LN1