Director of Finance

The Opportunity

The Red Fox Inn & Tavern has operated continuously since 1728. In 2028, it turns 300. That milestone isn't a celebration; it's a target. The organization is building toward its strongest revenue year in history in 2027, and the financial architecture to get there needs a leader, not a steward.

This is a newly elevated seat at the leadership table. The Director of Finance will own the full financial operating model of Middleburg Hospitality, a multi-entity, family-operated hospitality group that includes The Red Fox Inn & Tavern and Glenstone Gardens, and will be the Executive Director's primary strategic partner on every decision that involves capital, margin, or long-term financial health.

This is not a bookkeeping role. It is not a compliance role. It is a financial leadership role for someone who believes that the right numbers, in the right format, at the right cadence, are a competitive advantage.

What You'll Own

Financial operations and real-time visibility

• Build and maintain a living financial dashboard that leadership actually uses: not a monthly PDF, but a real-time view of revenue, margin, labor cost, and cash position across all departments and entities
• Lead monthly, quarterly, and annual close processes with accuracy and speed
• Own departmental P&L management across Rooms, F&B, and Events, with the discipline to hold department heads accountable to their numbers and the credibility to be trusted when you do it
• Manage cash flow, liquidity, and multi-entity intercompany arrangements with full transparency to ownership

FP&A and forward-looking modeling

• Lead annual budgeting and rolling forecast cycles, building models that are designed to be tested against reality, not filed and forgotten
• Build 13-week cash flow forecasts and scenario models that give leadership clear visibility into multiple futures, not just the expected one
• Translate hospitality performance metrics (RevPAR, ADR, occupancy, F&B margin, labor ratios) into financial models that connect operational decisions to EBITDA outcomes
• Provide proactive financial analysis during capital planning, renovation decisions, and milestone initiatives including the 300th anniversary build

Cost and margin control

• Monitor and report on labor cost as a percentage of revenue across all departments, with real benchmarks and actionable commentary rather than just variance flags
• Analyze F&B cost of goods, vendor contracts, and procurement efficiency on a cadence that enables decisions, not just reviews
• Identify margin opportunities that go beyond cutting costs by modeling the revenue mix, channel economics, and departmental contribution to total profitability

Entity structure, tax strategy and family financial alignment

• Map, evaluate, and help optimize the existing multi-entity ownership structure across operating companies, holding entities, and family trusts, with an eye toward reducing unnecessary tax exposure and improving structural clarity
• Partner with external tax counsel and CPAs to identify and execute entity-level tax strategies, including income allocation, depreciation planning, intercompany pricing, and timing of distributions
• Manage intercompany transactions with precision: loans, management fees, shared service allocations, and cost-sharing arrangements across entities must be documented, defensible, and optimized
• Serve as the primary internal financial resource for ownership on matters where personal and business finances intersect, including trust distributions, capital contributions, and family liquidity needs
• Maintain awareness of estate and succession planning considerations as they relate to the financial structure of the business, and coordinate with family advisors as needed
• Ensure all entity-level filings, K-1s, and ownership reporting are accurate, timely, and clearly communicated to the family

Compliance, payroll and regulatory oversight

• Oversee payroll systems and reporting with accuracy and full regulatory compliance across all entities
• Manage tax filings and financial compliance across the full entity structure, coordinating with external accountants, auditors, and legal counsel as needed
• Maintain a clean, auditable paper trail across all intercompany and family-related transactions

Strategic partnership

• Serve as a true financial thought partner to the Executive Director, bringing analysis and perspective to strategic decisions before being asked, not just when asked
• Collaborate with the Director of Operations, Inn Director, F&B Director, and Director of Events to connect their operational realities to the financial model
• Translate complex financial data into clear, concise summaries for non-financial leaders and, when appropriate, for family ownership

What We're Looking For

Experience and background

• 8 to 15 years of progressive financial leadership, with meaningful time in a senior or director-level seat
• Hospitality, hotel, resort, multi-unit F&B, or luxury lifestyle operations experience strongly preferred; you should walk in understanding what RevPAR means and why it matters
• Demonstrated experience with multi-entity structures, family-owned business dynamics, or complex ownership arrangements; this is not an environment for someone who needs clean corporate infrastructure to perform
• Direct experience working with family trusts, holding companies, or intercompany structures where tax optimization and ownership alignment are active, ongoing responsibilities, not one-time setup work
• Comfort operating at the intersection of business finance and family financial interests, with the discretion and emotional intelligence that environment demands
• CPA strongly preferred given the tax complexity of this role; MBA or equivalent is a meaningful plus

Technology and systems fluency

The incoming Director of Finance will inherit a clearly defined finance and reporting stack and will be expected to optimize, integrate, and lead it from day one. Familiarity with these specific platforms — or their direct equivalents — is a meaningful advantage:

• Sage: primary general ledger and P&L system; several automated integrations are in progress and will require the Director of Finance to own completion and ongoing accuracy
• Fathom: forward-looking budgeting, forecasting, and cash flow visibility; connects directly to Sage and is a near-term implementation priority
• Power BI: live revenue dashboard aggregating data from Sage, Excel, Google Analytics, Google Ads, Meta, and HubSpot; included in the existing Microsoft 365 license
• Excel: financial modeling, ad hoc reporting, and budget templates; the Excel sales tracker feeds directly into Power BI
• ADP: payroll, tax filing, tip distribution, and employee records; ADP-to-Sage payroll sync is a confirmed integration on the roadmap
• Stripe: payment processing across all revenue streams; Stripe-to-Sage auto-posting is a current-week priority
• Toast: F&B POS and daily sales reporting; Toast-to-Sage integration via Shogo middleware is a 90-day roadmap item
• MarketMan: food and beverage cost reporting, margin tracking, invoice management, and supplier spend; native MarketMan-to-Sage integration is confirmed
• HubSpot: events pipeline, deal tracking, and marketing ROI reporting
• Monday.com: compliance calendar, renewal reminders, and certification tracking
• SharePoint: financial document storage, bank records, and compliance files
• DocuSign: vendor contracts, supplier agreements, and financial authorizations

Genuine working familiarity with AI tools applied to finance — including AI-assisted variance commentary, automated reporting summaries, and anomaly detection — is expected; not theoretical awareness but actual daily use.

The right mentality

• You think of financial clarity as a form of leadership, not a support function
• You are comfortable being the person in the room who says what the numbers actually mean, even when that is uncomfortable
• You operate with professional discretion and understand what it means to earn the trust of long-tenured ownership and staff
• You are energized by complexity, not paralyzed by it

Compensation and Location

Base salary: $135,000 -$150,000 annually, commensurate with experience

Total compensation package includes:

• Annual performance bonus of up to 10% of base salary, tied directly to EBITDA margin improvement, forecast accuracy, and financial efficiency targets
• Full health, dental, and vision insurance
• Annual professional development budget for tools, certifications, and conferences

Location: This is a full-time, in-office role based in Middleburg, Virginia. We are looking for someone who wants to be present, embedded, and genuinely part of this community, not managing it from a distance. Middleburg is one of the most beautiful and distinctive towns in Virginia, and for the right person, that is a feature of this role, not a footnote. Candidates must be based in or willing to relocate to the DC metro, Northern Virginia, or Charlottesville corridor.

Why This Role, Why Now

Most finance roles at properties like this are backward-looking by design. This one is not. The organization has genuine appetite for modernization in its reporting, its tooling, and its decision-making, and the incoming Director of Finance will have real authority to build the financial infrastructure that carries it into its next century.

The 300th anniversary is not a marketing moment. It is a financial milestone that requires the right model, the right margins, and the right leader to make it mean something.