Staff Data Scientist - Finance & Accounting

About the Role:

As a Staff Data Scientist for Finance and Accounting, you will drive data insights strategy for Headway's financial ecosystem. Your mission is to provide a holistic understanding of our financial health and our revenue infrastructure.

You will report into the Data team and support Headway's Insurance Group, a mission critical pillar that ensures the systems behind our insurance platform reliably power patient, provider, and payer experiences. Accurate and complete financial visibility is a core part of our operations and essential to Headway's growth.

You will partner closely with both the Finance department (including Accounting, Strategic Finance, and FP&A teams) and Engineering, Product, and Operations teams in our Revenue Engine R&D pods to improve our revenue infrastructure and financial reporting. You will define the right questions, uncover opportunities, and work cross-functionally to turn insights into measurable improvements in how we track and report financial performance. In doing so, you will provide a timely and trusted view into company performance that shapes our customer experience and supports Headway's path to public company readiness.

What You’ll Do:

• Drive insights and decisions through strategic analysis, reporting, and predictive modeling.
• Design a metrics framework that connects our revenue infrastructure to financial outcomes, surfacing gaps in our data and reporting.
• Define and drive the measurement strategy for collections loss. Build the frameworks we use to understand where and why loss occurs, set targets for improvement, and identify the highest-ROI opportunities to reduce loss so they can be translated into cross-functional initiatives.
• Build forecasts that inform staffing decisions and help us estimate how we’re tracking against goals.
• Partner cross-functionally to ensure our revenue systems provide the auditability and data traceability we need to be GAAP compliant and audit-ready.
• Translate complex technical findings into clear, actionable recommendations for executive stakeholders.

What We’re Looking For:

• 10+ years of experience in data science or analytics roles.
• Working knowledge of core finance and accounting concepts such as how transaction-level data powers financial reporting (P&L, balance sheet, and cash flow statement).
• Experience working with healthcare Revenue Cycle Management (RCM) is strongly preferred.
• Proven success partnering cross-functionally with Finance, Accounting, Product, Engineering, and Operations teams, and collaborating internally across Data Engineering and Data Science.
• Proficiency in forecasting and predictive modeling techniques.
• Experience with data modeling, ideally using dbt.
• Hands-on technical fluency in SQL and Python or R.
• Experience adopting and championing AI-assisted tools to accelerate and automate data workflows.
• Strong communication and stakeholder management skills.

Why This Role is Exciting:

• Help us uncover operational efficiencies that allow us to reinvest in building a better product and more effectively serve our customers.
• Influence the design and evolution of our financial systems, including the revenue sub-ledger and RCM, to ensure full financial visibility and GAAP compliance.
• Partner closely with senior and executive leadership and directly influence company strategy and growth.