We are hiring a Strategic Finance Associate to help build an AI-native finance function at Flagler Health. We sell software that automates clinic operations, and we intend for our own finance stack to run the same way: forecasting, reporting, billing, and deal analysis powered by clean data pipelines, LLM-driven workflows, and automation that gets smarter as the company grows.
Reporting to the VP of Finance, you will work directly with the CEO, Sales, RCM, and Clinical Operations. You will own the models and analyses that drive our biggest decisions, and you will design the automation that turns finance from a monthly reporting exercise into a real-time operating system for the business. Success means a forecast leadership trusts, a finance stack that runs largely on its own, and a Sales team that comes to Finance because it makes deals better and faster.
Planning & Reporting
Own the driver-based operating model and annual budget, and evolve them from static spreadsheets into a continuously updated forecast connected to live operational data
Build the monthly reporting package for leadership and investors, and automate the data pipeline behind it so the numbers are ready before anyone asks
Build and maintain unit economics by customer, clinic, and service line (RTM, CCM, advanced therapy programs, RCM services), and make them the shared language for pricing and growth decisions
Own headcount and cash planning, including runway scenarios and the analysis behind hiring, vendor, and capital-allocation decisions
AI & Finance Automation
Design and ship AI-driven workflows across the finance stack: invoicing, collections follow-up, reconciliation, variance commentary, and reporting
Use LLMs, agent frameworks, and light scripting to eliminate manual steps between our systems (billing, banking, cap table, BI) and keep them in sync
Evaluate, select, and implement the tools that take us beyond spreadsheets, and set the standards for documentation, monitoring, and data integrity as the stack matures
Revenue Operations & Deal Support
Qualification
Bias toward actionStrong financial modeling and analysisHands-on technical aptitude with dataStrong written and verbal communicationExposure to healthcare servicesExperience at a Series A–C startupWork Environment
Required
2–4 years of experience in investment banking, management consulting, private equity / growth equity, or strategic finance / FP&A at a high-growth company, plus a bachelor's degree.
Bias toward action: comfortable scoping an ambiguous question, breaking it down, and delivering a working model and a clear recommendation end-to-end.
Strong financial modeling and analysis: driver-based operating models, unit economics, scenario and sensitivity analysis, and a clear sense of where a model is directionally useful versus where it breaks down.
Genuine fluency with modern AI tooling (LLMs, agent frameworks, prompt engineering) and a clear sense of where AI works well in a finance workflow versus where it breaks down.
Hands-on technical aptitude with data: advanced Google Sheets / Excel, working SQL, and light scripting (Python or similar). You don't need to be an engineer, but you should be able to pull your own data, build your own automations, and debug your own work.
Strong written and verbal communication, able to translate between financial, technical, and non-technical stakeholders, with an ownership mindset about outcomes rather than scope.
Preferred
Exposure to healthcare services, revenue cycle, or other regulated industries. We care more about how fast you learn the domain than what you've already seen
Experience at a Series A–C startup, ideally as an early finance hire
Familiarity with healthcare reimbursement (Medicare fee schedule, RTM/CCM/PCM billing, CPT-driven revenue) and practice-level P&Ls
Familiarity with MSO/PC entity structures and multi-entity reporting
Experience with a modern finance stack (e.g., Bill.com, Carta, QuickBooks/NetSuite, Metabase or another BI tool) and with implementing new tools
Work Environment:
This role requires regular and consistent in-person collaboration
We maintain a highly collaborative culture with video-on team meetings and technical discussions
