Position Overview

The Office Manager & Bookkeeper serves as the central administrative, financial, and operational coordinator for the Charlottesville office of Big Lick LLC and affiliated Owner family entities. 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.

Key Responsibilities

1. Bookkeeping & Accounts Payable

• Enter and manage all financial transactions in QuickBooks across multiple entities
• Perform bank and credit card reconciliations
• Manage full-cycle accounts payable, including: Processing invoices (email/mail): Coding transactions to appropriate entities; Managing Ramp invoice routing and approvals
• Execute payments via ACH, wire, check, and credit card platforms
• Ensure proper documentation, approvals, and compliance for all transactions
• Maintain organized financial records and documentation
• Serve as a resource for internal accounting questions

2. Treasury & Cash Management

• Coordinate and manage cash movements between the Owner's family and affiliated businesses
• Prepare weekly cash position summaries and funding needs
• Ensure adequate liquidity across all entities
• Track intercompany loans and financial obligations
• Support financial oversight and internal controls

3. Property & Office Management

• Oversee operations for:
• 703 East Jefferson Street (office building)
• 707 E. Market Street (Jefferson Guest House)
• Manage: Tenant relations and office rentals at 703; Lease administration and amendments; Conference room scheduling and shared space coordination
• Coordinate with Stay Charlottesville on Guest House operations
• Manage:
• Basement apartment leasing (direct rental)
• Vendor coordination, maintenance, and issue resolution
• Security systems, alarms, and digital access

4. Vehicle & Asset Management

• Maintain all records for vehicles owned by Big Lick and the Owner family, including: Registrations; Insurance; Maintenance tracking
• Coordinate service, repairs, and compliance

5. Administrative & Executive Support

• Serve as the primary onsite administrative resource in Charlottesville
• Support Risk Manager and remote leadership with operational needs
• Field and manage personal and business-related requests from personal family members
• Handle incoming mail, documents, and recordkeeping
• Maintain office supplies and general office functionality
• Assist with special projects and evolving operational needs

Work Environment

• Small, high-functioning office with one additional full-time onsite employee and an
• Office for the owner who’s frequently works there
• High level of interaction with ownership and senior leadership
• Requires discretion, professionalism, and adaptability

Qualifications

• Experience in bookkeeping, accounting, or financial operations (QuickBooks preferred)
• Strong organizational and multitasking abilities
• High attention to detail and accuracy
• Ability to handle confidential information with discretion
• Comfortable working across multiple businesses and priorities
• Strong communication and problem-solving skills
• Experience with property management or office operations is a plus