Director of Finance, Controller

Trump Winery • Charlottesville, VA

2d • Onsite

About The Position

Trump Winery is seeking an experienced, detail-driven Director of Finance/Controller to lead all accounting and compliance functions across our winery and hospitality businesses. As a key member of the leadership team, this hands-on financial leader oversees accounting operations, financial reporting, budgeting, and compliance—ensuring financial integrity while providing strategic support for business growth. The role manages a two-person team (an AP/Purchasing specialist and a staff accountant) and partners closely with department leaders across the organization. This is an exciting opportunity to contribute to one of Virginia’s premier wineries while working in a collaborative and dynamic setting.

Requirements

• Bachelor's degree in Accounting, Finance, Economics, or related equivalent experience
• 5+ years of progressive accounting and financial experience
• Exceptional organizational skills, attention to detail, and ability to manage multiple deadlines
• Strong communication skills and ability to collaborate across departments
• Expertise in accounting software and advanced Excel skills
• Ability to lead and mentor financial operations team

Nice To Haves

• Experience in winery, hotel, agriculture, or hospitality a plus

Responsibilities

• Lead and supervise all accounting operations: AP/AR, general ledger, financial statements, and tax compliance, licensing
• Produce timely P&L statements, balance sheets, cash flow reports, and other financial analyses.
• Develop annual operating and capital budgets with the General Manager and department leaders; track budget vs. actuals and deliver variance explanations and recommendations
• Manage banking activity, cash flow monitoring, reconciliations, and weekly cash flow reporting; approve bank transactions, wires, ACH, and capex purchase requests
• Maintain an organized accounting filing system and accurate chart of accounts.
• Coordinate with external CPAs for annual tax returns, tax planning, and preparation of documentation for taxes and compliance
• Issue annual 1099s and maintain compliance with all reporting deadlines.
• Oversee monthly, quarterly, and annual sales tax and excise tax filings (mostly through third-party software; some manual)

Benefits

• Health Coverage: We cover 80% of the employee premium on our base medical plan and 40% for dependents. Choose from low-deductible and HSA-compatible options.
• Dental & Vision: We pay 80% of dental and vision premiums
• Generous Time Off: Enjoy 26 days of paid time off each year, combining vacation, sick time, and holidays.
• Income Protection: Employer-paid short-term disability coverage.
• Additional Voluntary Benefits: Optional employee-paid Life, AD&D, and Accident plans.
• 401(k) Retirement Savings: After one year, 100% match on the first 3% you contribute and a 50% match on the next 3%.

What This Job Offers

• Job Type: Full-time
• Career Level: Director