Bookkeeper & Office Manager

Job Description

Job 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

  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

• Salary: $70,000 – $85,000 Annual Salary
• 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

• 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