Location: Remote

Reports To: Chief Executive Officer (CEO)

Employment Type: Full-Time

About Stakeholders VR

Stakeholders VR is assembling a first-of-its-kind Supergroup in the vacation rental industry. Backed by private equity, we’re acquiring and integrating the best independent property management companies across North America to form a premium, high-performing national platform. With 30 Property Management companies, we are creating a roll-up that protects legacy brands, unlocks growth, and delivers institutional-level returns.

This is not your average CFO role. It’s a chance to build the financial backbone of a platform designed to redefine what’s possible in the vacation rental space.

The Role

As Chief Financial Officer, you will be the strategic and operational leader of all financial functions across our multi-entity structure. You’ll lead M&A diligence, post-close integration, capital strategy, investor reporting, and financial infrastructure for a platform that spans 30+ regional operators and is being engineered for future institutional investments.

We’re looking for a proven financial leader who can scale systems and teams, partner with private equity, and create clarity in complexity. Someone who is equally comfortable in the boardroom, on diligence calls, and in the weeds of integration.

Key Responsibilities

Strategic Finance & Planning:
Develop and execute the financial roadmap aligned with growth, M&A, and performance objectives.
Private Equity & Capital Strategy:
Partner closely with PE sponsors and investors on capital deployment, structuring, and return modeling.
M&A Execution:
Lead financial diligence, deal modeling, and integration playbooks for a high-volume acquisition cadence.
Multi-Entity Integration:
Standardize accounting practices, unify systems, and consolidate financial reporting across 30+ operating companies.
Reporting & Controls:
Build a centralized finance team that delivers GAAP-compliant, audit-ready reporting, while ensuring strong internal controls.
Technology & Systems:
Oversee implementation and integration of ERP systems, property management platforms (PMS), and BI tools.
Team Building:
Scale the finance organization, including shared services, FP&A, accounting, tax, and treasury.
Stakeholder Communication:
Deliver timely, transparent reporting to the CEO, Board, investors, and future institutional buyers.

Ideal Candidate

10+ years of progressive finance experience, with 3+ years in a CFO or top finance leadership role
Proven experience in PE-backed, multi-entity, M&A-intensive environments
Strong understanding of hospitality, real estate, vacation rentals, or similar operationally complex businesses
Fluent in transaction structuring, post-close integration, and financial modeling
Systems-savvy with ERP/PMS experience (NetSuite, QuickBooks Enterprise, etc.)
Track record of scaling finance functions from early stage to exit
High EQ, low ego, and a passion for building something enduring with a high-performing team

Why Join Stakeholders VR

Equity Participation: Be part of the value you help create
High-Growth Platform: Join a PE-backed roll-up with real momentum
Mission-Driven Culture: Work with passionate, entrepreneurial operators across North America
Remote & Flexible: Work from anywhere with a team built on trust, accountability, and shared outcomes
Legacy + Upside: Help shape the future of an industry while protecting the legacy of local brands

To Apply:

Send your resume and a short note about why you’re interested to: brandon@stakeholders.us

Stakeholders VR Supergroup Jobs

Chief Financial Officer (CFO) | Stakeholders VR