Bookkeeper & Office Manager

Job DescriptionJob 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.

Ready to make your application Please do read through the description at least once before clicking on Apply.

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: 23 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. xhqgsiq Flexibility and a proactive mindset are essential and genuinely valued here.

ENTITIES SUPPORTED

Big Lick LLC

Big Lick Stall Rental ( )

Black Prong ( )

All-In Removal ( )

Nature Coast Soils ( )

Additional Nagle family financial and personal interests