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 FP&A.
• 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), with a focus on the operationalization of billing policies.
• Communication: Excellent communication skills, with the ability to clearly articulate complex operational and data issues to both staff and executive leadership.

Nice to Have

• Ideally with experience in the Property Management and/or Real Estate industry.

Travel Required

n/a

Location

Bay Area (Oakland), CA. This is a 3 day hybrid role in the Oakland office.

Compensation

$salary range - $salary range annually 

Compensation may be adjusted based on experience, skills, and interview performance.

Pay Transparency

Our compensation reflects several US geographic markets. The base pay for this position represents the expected salary for this position.  Ultimately, in determining your pay it will be based on several factors including location, job-related knowledge, skills, experience and other job related factors.  Roofstock is a total compensation company; the base salary is only a part of our total compensation package.

Competitive & Unique Benefits Package

• Generous PTO Policy
• 12 Paid Holidays
• Volunteer Time Off
• Paid Parental Leave
• 401k Program
• Wellness and home office/cell phone subsidies
• Robust health, dental, vision insurance, and more
• Wellness and home office/cell phone subsidies 

Must be authorized to work in the U.S. is a precondition of employment and we are unable to sponsor H1-B Visas at this time.

Any offer of employment is conditioned upon the successful completion of a background investigation.  

Commitment to Equal Employment Opportunity 

Roofstock is an equal opportunity employer. In keeping with the values of Roofstock, we make all employment decisions including hiring, evaluation, termination, promotional and training opportunities, without regard to race, religion, color, sex, age, national origin, ancestry, sexual orientation, physical handicap, mental disability, medical condition, disability, gender or identity or expression, pregnancy or pregnancy-related condition, marital status, height and/or weight.

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