Senior Associate, Payment Operations

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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 care across the nation.

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 by serving as the critical operational bridge to our Accounting and Payments Data functions. This role is core to ensuring the financial integrity of our business and will provide you with deep exposure to the unique mechanics of the healthcare system.

As a Senior Associate, you will have the unique opportunity to create structure out of chaos within our financial processes. You will architect, test, and operationalize solutions that ensure our financial records accurately reflect our real-world operations. This is an opportunity to get hands-on in a data-first environment, use your analytical and accounting experience, and own outcomes core to the financial accuracy and growth of our business. This role will live on our payments operations team.

What you’ll do at Headway:

• Lead operational components of the business close process, liaising frequently with the Accounting team to ensure a timely and accurate monthly close.
• Serve as the go-to Operations contact to confirm that the financial ledger accurately reflects the true operational state of the business.
• Classify and reconcile operational financial data, including classifying Accounts Receivable (A/R) and Accounts Payable (A/P) to ensure proper recording and reporting.
• Coordinate and execute write-off processes across the Operations function, ensuring appropriate documentation and alignment with financial policies.
• Design, build, and implement scalable processes and controls to improve the efficiency and quality of our financial data workflows.
• Work cross-functionally with Product, Engineering, Payer, and CX teams to drive system improvements that streamline the Revenue Cycle Management (RCM) process and enhance financial integrity.

You’ll be great for this role if you:

• 3-5 years of experience in accounting, finance, operations, or investment banking; operational finance or accounting experience at a high-growth startup is a plus.
• Have a strong foundational understanding of basic accounting principles and financial  concepts.
• You are a systems thinker who is inclined to solve financial and operational problems with product, automation, and scalable processes.
• You are highly data-driven. Can drive complex analyses on financial data and translate those findings into actionable insights, process improvements, and OKRs.
• You are a self-starter. Master disambiguator/simplifier and constantly pushing toward clarity and execution in a fast-paced environment.
• You are a collaborator. Proactively partner across teams, particularly with Finance and Accounting, while holding operational teams accountable for the quality of financial inputs.

Compensation and Benefits:

• The expected base pay range for this position is $84,320-$124,000, 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