Controller

About the role

A well-established private family office and investment organization is seeking an organized, experienced Controller to oversee accounting operations across a diverse portfolio of operating companies, real estate holdings, trusts, and personal family finances. This leadership role will manage a small accounting team while serving as the primary financial liaison to ownership, tax advisors, and external service providers. The ideal candidate will bring strong multi-entity accounting expertise, process improvement experience, and the ability to operate effectively in a dynamic, entrepreneurial environment.

Responsibilities

Accounting Leadership & Financial Management

• Lead, mentor, and develop a team of 3–4 accounting professionals.
• Oversee accounting operations for 25+ legal entities, trusts, and operating businesses using QuickBooks Enterprise.
• Strengthen internal controls, workflows, and accounting procedures across the organization.
• Drive timely and accurate month-end close processes and financial reporting, including accelerating the monthly close process to consistently close within 10 business days.
• Prepare financial schedules and reporting packages for ownership and external advisors.
• Maintain professional and confidential communication with ownership and key stakeholders.

Multi-Entity Business Accounting

• Convenience Store: Manage comprehensive inventory tracking, including fuel and regulated products, and prepare sales tax filings.
• Winery: Manage cost accounting, bulk wine inventory coordination, TTB filings, and sales and excise tax reporting.
• Restaurant & Hotel: Oversee tip reporting, payroll coordination, and monthly cash and petty cash reconciliations.
• Real Estate & Construction: Manage CIP accounting, job costing, CAM reconciliations, and provide support for legal and CPA reviews.
• Insurance Administration: Manage employee health plans, property and liability insurance, and life insurance administration.

Trust, Investment & Family Office Accounting

• Oversee accounting and reporting for multiple trust entities.
• Track loans, reimbursements, credit card activity, and intercompany transactions.
• Record and reconcile investment activity, including brokerage and alternative investments.
• Manage personal financial accounting and bill-pay activities for ownership.
• Ensure accurate recordkeeping across all family office and investment-related activities.

Systems & Tools

• QuickBooks Enterprise (separate files per entity)
• Paychex for payroll
• Excel
• POS system: Commerce7
• Wine production software: Vintrace
• Event management software: Perfect Venue

Qualifications

• 10+ years of progressive accounting experience.
• 5+ years of accounting leadership or management experience.
• Proven experience managing complex, multi-entity accounting environments.
• Strong leadership, organizational, and project management skills.
• Demonstrated success implementing process improvements and automation initiatives.
• Ability to manage competing priorities while meeting deadlines.
• High degree of professionalism, confidentiality, and attention to detail.

Preferred

• Experience within family office, private investment, real estate, construction, hospitality, retail, or related industries.
• CPA designation preferred but not required.
• Experience supporting ownership groups, investors, or high-net-worth individuals.
• Advanced accounting systems and financial reporting expertise.

What Success Looks Like

• Consistently delivering accurate and timely financial reporting.
• Maintaining strong internal controls and clean financial records across multiple entities.
• Building a high-performing accounting team.
• Providing meaningful financial insights to ownership and advisors.
• Driving operational improvements that enhance efficiency, scalability, and business performance.