Controller

Controller

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.

Key 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

Required

• 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.

Determining compensation for this role (and others) at Vaco/Highspring depends upon a wide array of factors including but not limited to the individual’s skill sets, experience and training, licensure and certifications, office location and other geographic considerations, as well as other business and organizational needs. With that said, as required by local law in geographies that require salary range disclosure, Vaco/Highspring notes the salary range for the role is noted in this job posting. The individual may also be eligible for discretionary bonuses, and can participate in medical, dental, and vision benefits as well as the company’s 401(k) retirement plan. Additional disclaimer: Unless otherwise noted in the job description, the position Vaco/Highspring is filing for is occupied. Please note, however, that Vaco/Highspring is regularly asked to provide talent to other organizations. By submitting to this position, you are agreeing to be included in our talent pool for future hiring for similarly qualified positions. Submissions to this position are subject to the use of AI to perform preliminary candidate screenings, focused on ensuring minimum job requirements noted in the position are satisfied. Further assessment of candidates beyond this initial phase within Vaco/Highspring will be otherwise assessed by recruiters and hiring managers. Vaco/Highspring does not have knowledge of the tools used by its clients in making final hiring decisions and cannot opine on their use of AI products.