Director of Revenue Operations & Billings

What we do and why we do it As the leading end-to-end investment platform for single-family rental homes (SFR), our mission is to reinvent the rental housing ecosystem for the benefit of all. We successfully merge our passion for helping investors build wealth through real estate with cutting edge technology that transforms the way they do it. How it’s going (and growing) With a talented team of 750+ Roofsters, our collaborative, can-do culture is what fuels our growth. In 2022, we closed on our Series E, raising $240 million, and have offices in the Bay Area and New York City. Our growth includes recent acquisitions of Stessa (financial and asset management software), RentPrep (tenant screening and placement service for landlords), and Mynd (property management platform for both Retail and Institutional investors). In 2025, Roofstock took an ownership stake in Casago (short-term rental management services), expanding our platform to support both long-term and short-term rental investment services. About the Role The Director of Revenue Operations Billings is a critical, hands-on leadership role responsible for owning the company’s revenue cycle and related billing operations for our multiple business units. This individual will serve as a player-coach, leading a team of four while personally driving complex spreadsheet calculations, journal entries, and flux analysis. The successful candidate should be skilled at automating highly manual processes that currently rely on complex spreadsheets. Responsibilities Lead Process Automation: Champion the transformation of manual, spreadsheet-based workflows into automated, system-driven processes. Successfully identify, evaluate, and implement system enhancements, automation tools, and AI solutions to scale the department and eliminate heavy manual effort. Billing and Revenue Cycle Ownership: Fully own the end-to-end billing and revenue cycle across the organization, ensuring accurate and timely billing operations that align with revenue recognition policies. Assist in the monthly financial close process, ensuring all deadlines are met and financial statements are accurate and compliant with US GAAP. Own and drive accounting projects such as system implementations, process improvements, policy updates, accounting memos, and internal control enhancements. Data Calculation Mastery: Serve as the final authority on the accuracy of large data sets used for revenue calculation, personally reviewing and validating spreadsheets and related analysis. Financial Reporting Analysis: Lead monthly revenue variance analysis, providing detailed, operational insights into revenue trends and drivers for the CFO and FPA. Team Leadership: Act as a hands-on player-coach to the revenue team (4 total staff, 2 direct reports), providing technical guidance, mentoring, and support to ensure work quality and professional development. Audit Liaison: Support our external audit process on revenue and billing matters, providing robust documentation and clear explanations to ensure audit readiness. Cross-Functional Partnership: Act as a key liaison across Finance, Sales, Legal, and IT to drive alignment on contract terms, billing systems, data accuracy, and system requirements. Qualifications Bachelor’s degree in Accounting or Finance required Industry Expertise: Minimum of 8+ years in a senior revenue operations and billing role 5+ years of experience managing a team Automation Track Record: Proven success in transforming highly manual, volume-heavy processes into automated, system-driven workflows. Technical Tool Mastery: Expert-level Excel skills and proficiency in financial reporting tools (e.g. VLOOKUP, Pivot Tables, Macros, etc). Comfortable owning, auditing, and manipulating large data sets. Operational Mindset: Strong process orientation with a focus on efficiency, control, and standardization. GAAP Knowledge: Solid understanding of GAAP revenue recognition principles (ASC 606 ... (truncated, view full listing at source)