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Flagler Health is building an AI-native clinical operating system for musculoskeletal care providers. The company partners with MSK provider groups and specialty clinics to help them grow, operate efficiently, and deliver better longitudinal care. Recently closed a Series B funding round and is entering its next phase of growth.
As Strategic Finance Associate reporting to the VP of Finance, you will be the core builder of Flagler's finance function, working directly with the CEO, Sales, RCM, and Clinical Operations teams. Your mission is to transform finance from a monthly reporting exercise into a real-time operating system powered by clean data pipelines, LLM-driven workflows, and automation.
Key responsibilities span three main areas:
Planning & Reporting: Own the driver-based operating model and annual budget, evolving them from static spreadsheets into continuously updated forecasts connected to live operational data. Build and automate the monthly reporting package for leadership and investors. Establish and maintain unit economics by customer, clinic, and service line (RTM, CCM, advanced therapy programs, RCM services) as the shared language for pricing and growth decisions. Own headcount and cash planning, including runway scenarios and 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 systems (billing, banking, cap table, BI) and keep them in sync. Evaluate, select, and implement tools that move the organization beyond spreadsheets, setting standards for documentation, monitoring, and data integrity.
Revenue Operations & Deal Support: Own the analytics behind order-to-cash, including revenue recognition, AR and collections performance, and reconciliation of billed revenue against RCM and care-management activity. Serve as the finance partner to Sales, providing pricing and discounting analysis, deal structure guidance, and customer-facing ROI and pilot-results analyses. Assess prospective customers' practice financials to size opportunities from RCM, RTM/CCM, and other programs.
Corporate Finance: Support corporate development work, including diligence, valuation, and deal-economics analysis for partnerships, carve-outs, and acquisitions. Support cap table administration, treasury operations, and investor reporting.
The role requires regular and consistent in-person collaboration in the NYC office, with a highly collaborative culture emphasizing video-on team meetings and technical discussions.
REQUIREMENTS:
- 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 ambiguous questions, breaking them down, and delivering working models and clear recommendations end-to-end
- Strong financial modeling and analysis: driver-based operating models, unit economics, scenario and sensitivity analysis, with clear judgment about where models are directionally useful versus where they break down
- Genuine fluency with modern AI tooling (LLMs, agent frameworks, prompt engineering) and clear sense of where AI works well in finance workflows versus where it breaks down
- Hands-on technical aptitude with data: advanced Google Sheets/Excel, working SQL, and light scripting (Python or similar). Ability 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 QUALIFICATIONS:
- Exposure to healthcare services, revenue cycle, or other regulated industries
- 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 (Bill.com, Carta, QuickBooks/NetSuite, Metabase or another BI tool) and with implementing new tools
