Grand Welcome, CFO

Grand Welcome
Chief Financial Officer

Greybull Stewardship is seeking an experienced Chief Financial Officer (CFO) for one of its portfolio companies, Grand Welcome, a leading franchisor and operator in the short-term vacation rental industry.

Grand Welcome combines cutting-edge technology, deep local market expertise, and a customer-first mindset to deliver exceptional value to homeowners, guests, and franchise partners. With ambitious growth plans – including organic franchise expansion and targeted acquisitions of smaller STR operators – and a focus on achieving sustainable profitability, we are seeking a strategic, hands-on finance leader to:

• Own Grand Welcome’s financial strategy and capital allocation
• Optimize unit economics across both franchise and company-owned markets
• Build scalable systems, processes, and teams
• Partner closely with the CEO, PE sponsor, and leadership team to drive value creation

This role is ideal for someone with a scale-up mentality who has helped build or transform finance functions in high-growth, multi-unit or franchised businesses and is comfortable operating at both the strategic and “roll-up-your-sleeves” levels.

Key Responsibilities

Strategic & Financial Leadership

• Serve as a key thought partner to the CEO and a core member of the leadership team, helping shape and execute the company’s long-term growth strategy.
• Lead development of the financial roadmap aligned to value creation goals (revenue growth, EBITDA, cash flow, leverage, and returns on invested capital).
• Translate company strategy into financial targets, dashboards, and operating KPIs for both corporate and franchise operations.

Planning, Forecasting & Performance Management

• Own the Annual Operating Plan (AOP), rolling forecasts, and long-range planning, including property- and territory-level modeling.
• Build robust unit economics, cohort, and channel profitability models to guide commercial, pricing, and investment decisions.
• Develop and maintain company-wide KPI dashboards (e.g., revenue per unit, RevPAR, franchisee EBITDA, SG&A leverage) and provide actionable insights to leaders and the Board.

Financial Operations & Controls

• Oversee all core finance functions: Accounting, AP/AR, Payroll, Revenue Recognition, Treasury, and Tax.
• Ensure accurate and timely monthly closes and Board reporting.
• Develop and maintain accounting policies, SOPs, and internal controls appropriate for a PE-backed, scaling business.
• Manage annual audits, tax filings, and relationships with external auditors and tax advisors.

FinTech / Systems & Data Infrastructure

• Lead the design and implementation of finance and data systems, including Sage Intacct, Guesty integrations, franchise billing and statement platforms, and payment/merchant solutions.
• Partner with Technology and Operations to build a scalable “franchise portal” and financial data infrastructure that integrates PMS, CRM, and accounting data.
• Drive automation of billing, collections, payouts, and franchisee financial reporting to improve accuracy, speed, and transparency.

M&A and Strategic Transactions

• Lead financial aspects of acquisitions of STR companies and potential franchise or territory deals: screening, financial modeling, valuation, due diligence, and integration planning.
• Build integration playbooks and financial frameworks for acquired businesses, including systems, reporting, and performance tracking.
• Evaluate strategic partnerships, JV structures, and asset-light growth opportunities.

Franchising & Multi-Unit Support

• Ensure reliable, timely, and transparent franchise financial reporting and statements, including royalties, brand fund, tech fees, and optional services.
• Partner with Franchise Development and Franchise Operations to assess territory performance, returns, and health of the franchise system.
• Develop financial tools and education to help franchisees manage profitability and growth.

Team Leadership & Culture

• Build, lead, and mentor a lean, high-performing finance team capable of scaling with the business.
• Foster a culture of ownership, accountability, and data-driven decision making.
• Champion cross-functional collaboration with Operations, Technology, Revenue/Commercial, Brand, and Franchise Development.

Qualifications – Experience & Background

• 10+ years of progressive financial leadership experience, including 5+ years in a CFO, VP Finance, or equivalent senior role.
• Experience in hospitality, property management, real estate, franchising, or multi-unit retail/consumer services strongly preferred.
• Prior responsibility in a PE-backed or high-growth scale-up environment, with a track record of building/transforming the finance function.
• Direct experience with:
• Scaling businesses and improving unit economics
• Leading significant systems / FinTech / finance tech projects (ERP, PMS integrations, billing, payments, data warehouses, BI tools)
• M&A evaluation, modeling, due diligence, and post-close integration
• Experience with Sage Intacct and Hospitality PMS is preferred.
• Strong understanding of technologies used to build and support software and data products in travel/hospitality is a plus.
• Experience from fast-paced start-up environment preferred.

Qualifications – Skills & Education

• Exceptional financial modeling and analytical skills; comfortable diving into details while keeping a board-level perspective.
• Demonstrated ability to design and manage KPIs, dashboards, and visualization tools for operators, franchisees, and investors.
• Proven track record building processes and teams that scale – not just maintaining status quo.
• Excellent management, communication, and stakeholder-management skills; able to influence across functions and with external partners.
• Bachelor’s degree in Finance, Accounting, Business Administration, or related field required.
• CPA preferred but not required if offset by significant relevant experience.

Application and Nomination: Review of applications will begin immediately and will continue until the position is filled. To apply for this position, please email a position-specific cover letter and resume to Jennifer Hiatt at jennifer@greybullstewardship.com. Nominations may be emailed to the same email address. Applicants needing reasonable accommodation to participate in the application process should also contact Jennifer Hiatt.