Accountant

Are you a detail-oriented financial professional who thrives in a dynamic, high-trust environment? This is a rare opportunity to serve as the financial and operational backbone of a closely-held family of businesses — with real ownership of your work, direct access to leadership, and a genuinely collegial team. ABOUT THE ROLE Based at our Charlottesville office (703 East Jefferson Street), the Bookkeeper & Office Manager is the central financial and operational coordinator for Big Lick LLC and its affiliated family-owned businesses. You will own the full bookkeeping cycle, keep cash flowing smoothly across multiple entities, and ensure the office — and the people in it — run without a hitch. This role blends bookkeeping, treasury support, property management, and executive-level administrative responsibilities. The position is responsible for managing financial transactions and cash movements across multiple family-owned businesses, maintaining office and property operations, coordinating vehicle management, and supporting the personal and business needs of the owner family. This is a high-trust, high-responsibility role requiring strong attention to detail, discretion, organization, and the ability to manage a wide variety of tasks across business and personal domains. WHAT YOU'LL DO Bookkeeping & Accounts Payable Enter & manage all financial transactions in QuickBooks across multiple entities Perform bank and credit card reconciliations Run full-cycle accounts payable — invoice processing, transaction coding, and Ramp approval routing Execute payments via ACH, wire, check, and credit card platforms Maintain organized, compliant financial records Be the go-to resource for internal accounting questions Treasury & Cash Management Coordinate cash movements across owner family and affiliated businesses Prepare weekly cash position summaries and funding needs Maintain adequate liquidity across all entities Track intercompany loans and financial obligations Support financial oversight and internal controls Property & Office Management Oversee operations for the office building (703 E. Jefferson St.) and the Jefferson Guest House (707 E. Market St.) Manage tenant relations, lease administration, and conference room scheduling Coordinate with Stay Charlottesville on Guest House operations Manage the basement apartment lease (direct rental) Coordinate vendors, maintenance, security systems, and digital access Vehicle & Asset Management Maintain records for all Big Lick and owner family vehicles Track registrations, insurance, and maintenance schedules Coordinate service, repairs, and compliance Administrative & Executive Support Serve as the primary onsite administrative resource in Charlottesville Support the Chief Risk & Contracting Officer and remote leadership Manage incoming mail, documents, and records Handle special projects and evolving operational needs Maintain office supplies and general functionality WHO WE'RE LOOKING FOR Bookkeeping experience is required for this role. Applications without a bookkeeping or accounting background will not be considered. Hands-on bookkeeping or accounting experience — REQUIRED · QuickBooks experience strongly preferred High attention to detail and a commitment to accuracy Strong organizational skills with the ability to juggle multiple priorities across different businesses Discretion and professionalism when handling confidential information Clear, confident communicator with strong problem-solving instincts Experience with property management or office operationsis a plus REPORTING STRUCTURE Primary Supervisor - Claudia Rrapokushi, Director of HR & Accounting Manager (remote) Site Supervisor - Christi Carel, Chief Risk & Contracting Officer Works Closely With - Owner family and leadership across all affiliated businesses COMPENSATION & BENEFITS Time Off: 2–3 weeks paid time off annually + 9 paid holidays (6 fixed + 3 floating) Health Insurance: $0 deductible. Company pays all but $100/month of employee premiums. Effective first day of the month after start date. Dental Insurance: Company-sponsored. You pay just $15/month for employee coverage. Vision Insurance: Company-sponsored. You pay just $3/month for employee coverage. Life Insurance: Company-paid $50,000 policy. Additional voluntary coverage available up to 3x salary or $150,000 (guaranteed issue). 401(k): Participate in the company plan with up to a 4% company match. Disability: Long-term and short-term disability insurance, fully employer-paid. WORK ENVIRONMENT This is a small, high-functioning office with one additional full-time onsite colleague and a dedicated office for the owner, who also works on-site regularly. You will have a high level of interaction with ownership and senior leadership, and the opportunity to make a meaningful, visible impact every day. The role is dynamic and will naturally evolve alongside the needs of the owner family and affiliated businesses. Flexibility and a proactive mindset are essential — and genuinely valued here. ENTITIES SUPPORTED Additional Nagle family financial and personal interests #J-18808-Ljbffr