Description:
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
Requirements:
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 operations is 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
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Salary: $70,000 – $85,000 Annual Salary
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Time Off: 2–3 weeks paid time off annually + 9 paid holidays (6 fixed + 3 floating)
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Health Insurance: $0 deductible. Company pays all but $100/month of employee premiums. Effective first day of the month after start date.
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Dental Insurance: Company-sponsored. You pay just $15/month for employee coverage.
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Vision Insurance: Company-sponsored. You pay just $3/month for employee coverage.
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Life Insurance: Company-paid $50,000 policy. Additional voluntary coverage available up to 3x salary or $150,000 (guaranteed issue).
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401(k): Participate in the company plan with up to a 4% company match.
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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
- Big Lick LLC
- Big Lick Stall Rental (biglick.com)
- Black Prong (blackprong.com)
- All-In Removal (all-inremoval.com)
- Nature Coast Soils (naturecoastsoils.com)
- Additional Nagle family financial and personal interests
