# Senior Director, Strategic Finance & Enterprise Planning at Oscar AI

- Company: Oscar AI
- What the company does: Oscar is an AI operations analyst that watches every location 24/7, catching revenue leaks, labor inefficiencies, and compliance risks, then delivering the alerts, reports, and action plans your team needs to fix them fast. Backed by Techstars.
- Company website: https://oscar.ai
- Type: Startups (AI role)
- Level: Principal and up
- Location: New York, New York, United States
- Work setup: On-site
- Pay: $219K to $287K base salary per year (USD)
- Posted: 2026-09-25
- Apply by: 2026-11-09
- Apply: https://job-boards.greenhouse.io/oscar/jobs/8224484
- Page: https://www.1752.vc/careers/jobs/oscar-ai-senior-director-strategic-finance-and-enterprise-planning/

## About the role

The Senior Director of Strategic Finance & Enterprise role will help lead the annual operating plan cycle, partnering with Finance, Strategy, and business leaders to translate company priorities into financial plans, targets, and executive-ready materials. You will also drive the strategic investment process by building business cases, evaluating trade-offs, and supporting resource allocation toward the company's highest-priority initiatives.

## What they're looking for

- 12+ years of experience in finance, FP&A, corporate strategy, investment banking, consulting, or a related strategic finance role
- Experience leading or supporting annual planning, budgeting, forecasting, long-range planning, or capital allocation processes
- Strong financial modeling, analytical, and business case development skills
- Influence senior stakeholders and drive alignment across cross-functional teams
- Excellent communication skills, with the ability to turn analysis into clear executive-level recommendations
- Strong project management skills and comfort operating in complex, fast-paced environments

Tags: Finance