Oscar is hiring a Revenue and Operations Senior Manager to lead the systems, processes, and insights that power the recurring revenue engine for our device and subscription business. In this role, you will serve as the connective tissue between Finance, Product, Customer Experience, and Engineering to ensure operational foundations are strong as the company accelerates.

What You'll Do

Manage the day-to-day health of the subscription billing ecosystem, including Stripe and internal systems.
Oversee processes for payments, refunds, credits, service suspension, and reactivation.
Monitor and reduce revenue leakage from failed payments and system discrepancies.
Partner with Product and Engineering to operationalize new plans, pricing, and regional rollouts.
Drive cross-functional initiatives aimed at reducing customer churn.
Maintain dashboards and recurring reports for ARR, churn, payment success, and billing accuracy.
Partner with Finance, Data, and Engineering teams on subscription forecasting and variance analysis.
Identify insights to improve attach, retention, and cash collection.
Continuously improve subscription operational workflows, including care refunds, credit issuance, and proration handling.
Ensure tight integration and data accuracy between Stripe, Databricks, and internal reporting tools.
Support quarterly audits and ensure compliance with PCI, SOC, and regional tax (VAT, 3DS, etc.) requirements.
Work closely with CX and Care to improve customer billing experiences.
Partner with the Marketing team to optimize billing communications.
Collaborate with the Product team on billing and subscription enhancements.
Partner with Finance on month-end close and revenue recognition accuracy.

What We're Looking For

5–8 years of experience in Revenue Operations, Subscription Billing, or Business Operations, ideally in SaaS, fintech, or consumer subscription businesses.
Hands-on experience with Stripe or equivalent billing platforms like Zuora, Recurly, or Chargebee.
Comfort working with data — extracting, cleaning, and summarizing insights.
Familiarity with Databricks and BI tools like Looker, Tableau, or Power BI.
Strong understanding of subscription metrics (ARR, churn, ARPU, LTV) and revenue workflows.
Analytical, detail-oriented, and process-driven.
Excellent communicator with the ability to work cross-functionally and explain complex topics clearly.
Comfortable working in a fast-paced, high-growth environment with evolving systems.

Nice to Have

Experience in a device + subscription business or other hybrid model.
Understanding of payments compliance, invoicing, or tax requirements (PCI, VAT, 3DS).
Hands-on Shopify experience to help integrate and improve e-commerce and revenue operations.
SQL proficiency or ability to self-serve data for analysis.

Technical Stack

Stripe, Databricks, Looker, Tableau, Power BI, Shopify, SQL

Team & Environment

You will act as the connective tissue between Finance, Product, Customer Experience, and Engineering.

Benefits & Compensation

Salary: USD $150,000–$180,000 per year.

Oscar is committed to inclusivity and selecting the strongest candidate—no matter their background. We value inclusion and are committed to an inclusive, and harassment-free workplace. Oscar is proud to be an Equal Opportunity Employer. We prohibit discrimination and harassment based on all legally protected statuses in all hiring and employment.