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 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 certification requirements; office location and other geographic considerations; and other business and organizational needs. With that said, as required by local law, Vaco/Highspring believes that the following salary range referenced above reasonably estimates the base compensation for an individual hired into this position in geographies that require salary range disclosure. The individual may also be eligible for discretionary bonuses and/or participation in medical, dental, and vision benefits as well as the company's retirement plan (or similar retirement benefits). Equal Opportunity Notice Highspring LLC (d/b/a Vaco by Highspring) and its parents, affiliates, and subsidiaries ("we," "our," or "Vaco by Highspring") are committed to the full inclusion of all qualified individuals and does not discriminate against any employee or applicant for employment because of race (including but not limited to traits historically associated with race such as hair texture and hair style), color, sex (includes pregnancy or related conditions), religion or creed, national origin, citizenship, age, disability, status as a veteran, union membership, ethnicity, gender, gender identity, gender expression, sexual orientation, marital status, political affiliation, or any other protected characteristics as required by applicable law. The company is also committed to ensuring that persons who need them are provided with reasonable accommodations; if an accommodation is needed to participate in the job application or interview process, please contact View email address on click.appcast.io . Vaco by Highspring also wants all applicants to know their rights that workplace discrimination is illegal. Representation Notice By submitting to this position, you agree that you will be giving Vaco by Highspring the exclusive right to present your as a candidate for the foregoing employment opportunity. Additionally, you agree to be included in our talent pool for future hiring for similarly qualified positions. You further agree that you have represented information about yourself accurately and have not affirmatively misrepresented your qualifications. Lastly, you agree to maintain as confidential, to the fullest extent permitted by law, any information you learn from Vaco by Highspring about the position and you will limit disclosure of information about the position only to the extent necessary to perform any obligations in furtherance of your application. In exchange, Vaco by Highspring agrees to exercise reasonable efforts to represent you through all solicitation, job screening and resume dispersal. For residents of Ontario, Canada only: to the extent the position for employment is not with Highspring or not otherwise noted as vacant above, candidate should be informed that this role is to replace a presently employed person at Vaco by Highspring's client. Privacy Notice Vaco by Highspring respects your privacy and are committed to providing transparent notice of our policies. California residents may access Vaco by Highspring HR Notice at Collection for California Applicants and Employees here. Virginia residents may access our state specific policies here. Residents of all other states may access our policies here. Canadian residents may access our policies in English here and in French here. Residents of countries governed by GDPR and UK GDPR may access our policies here. Additionally, 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. More details about Vaco by Highspring's use of AI can be found here Further assessment of candidates beyond this initial phase will be conducted by recruiters and hiring managers. Vaco by Highspring does not know and cannot opine on if its client's use of AI products in hiring. Pay Transparency Notice Determining compensation for this role (and others) at Vaco by Highspring depends upon a wide array of factors including but not limited to: the individual's skill sets, experience and training; licensure and certification requirements; office location and other geographic considerations; and other business and organizational needs. With that said, as required by local law, Vaco by Highspring believes that the following salary range referenced above reasonably estimates the base compensation for an individual hired into this position in geographies that require salary range disclosure. The individual may also be eligible for discretionary bonuses and/or participation in medical, dental, and vision benefits as well as the company's retirement plan (or similar retirement benefits). #J-18808-Ljbffr Vaco by Highspring