Job Description

Objective

The Head of Operations and Billing is a highly proactive, solutions-focused professional responsible for leading and supporting core operational, financial, and HR functions. This role functions as the operational center of the business, ensuring smooth day-to-day workflows, accurate billing and financial procedures, legal HR compliance, and consistent interdepartmental support. This role is both detail-oriented and big-picture focused, able to organize office procedures, build infrastructure, handle billing intricacies, and implement HR best practices with discretion and professionalism.

Key Responsibilities

Operational Management & Office Oversight

• Own the functionality of the HQ office, ensuring it is well-supplied, organized, and operating efficiently across departments.
• Collaborate with the CEO on setting operational priorities and executing initiatives aligned with company goals.
• Serve as the central point of contact for internal teams, external vendors, and retail managers to streamline communication and coordination of current initiatives.
• Support the implementation and enforcement of Standard Operating Procedures and Protocols across stores, eCommerce, inventory, and office personnel.
• Maintain all business licenses, vendor renewals, and ensure compliance with local, state, and industry regulations.
• Monitor and support operational software tools (e.g., Lightspeed, Shopify, G Suite), ensuring teams are trained and systems function as intended.
• Maintain and update company-wide Password & Credentials documentation for digital systems, accounts, and services.
• Coordinate all work-related travel arrangements, trade show accommodations, and logistics with vendors, designers, and executives.
• Oversee office supply ordering and replenishment for all departments including administrative, retail, and shipping.

Billing & Financial Coordination

• Manage the full billing cycle, ensuring vendor invoices are processed accurately and on time.
• Reconcile billing discrepancies and communicate directly with vendors to resolve any issues quickly and professionally.
• Maintain and organize documentation related to payments, including invoice records, payment confirmation, and reporting.
• Prepare weekly Accounts Payable packages in coordination with the company’s bookkeeper.
• Track payment schedules, due dates, and upcoming renewals for all operational subscriptions and services.
• Maintain clean and organized vendor files, including contracts, W-9s, pricing agreements, and payment terms in coordination with the Inventory Manager.
• Track and manage billing related to inventory orders in tandem with the Inventory Manager.
• Work with the CEO to assist on any budget tracking, vendor spend reporting, and financial projects.

Human Resources & Compliance

• Serve as the internal HR administrator for all employees, ensuring compliance with federal and state labor laws.
• Manage the full employee lifecycle: recruiting, interviewing, onboarding, benefits coordination, write-ups, and offboarding.
• Maintain and update the Employee Handbook and ensure all staff are informed of new legal and internal policies.
• Process payroll in coordination with store and office managers, including commission calculations and hours tracking including PTO, Sick Pay, Deductions, Reimbursements, etc.
• Conduct performance reviews in partnership with the CEO and maintain detailed employee performance records.
• Assist in maintaining confidentiality and compliance around sensitive employee data, including benefits, medical leaves, and terminations.
• Coordinate annual open enrollment for company-sponsored insurance and communicate updates to staff, accurately processing employee deductions in the payroll system.
• Draft employee documentation such as job descriptions, offer letters, disciplinary write-ups, and policy memos.
• Serve as the internal point of contact for all employee HR questions, concerns, or needs.
• Have a full understanding of all company positions, and be able to provide training and support if needed.
• Work with the CEO to conduct employee reviews, ensuring all procedures and protocols are being followed.

Departmental Support & Strategic Partnership

• Partner closely with the Inventory Manager to resolve discrepancies, assist with vendor communication, and ensure inventory processes are aligned with billing and reporting.
• Support retail store managers with backend operations including ordering, payroll issues, policy clarification, security, and resolving system-based inventory or POS issues.
• Provide in-person support to the local retail store, including organization, inventory management, and serving as a point of contact or leadership presence in the CEO’s absence.
• Work with eCommerce and marketing teams to streamline operational logistics around product launches, product data, and vendor communications.
• Represent the CEO and the company in external communications with vendors, service providers, and key business partners.
• Serve as a sounding board and strategic partner to the CEO, offering insight and logistical support on new initiatives, company policies, and business development ideas.
• Manage and update internal processes and workflows to ensure all team members understand their roles and responsibilities.
• Help mediate cross-team challenges and provide neutral, operational solutions to keep departments aligned.
• Ensure internal communication flows clearly and efficiently between the office, stores, remote teams, and vendors.

Professional Qualifications

• Bachelor’s degree in Business Administration, Operations Management, Accounting, HR, or a related field required.
• 4–6+ years of experience in operations, HR administration, billing, or office management (experience in luxury retail or eCommerce is strongly preferred).
• Deep understanding of HR laws, best practices, and compliance requirements.
• Hands-on experience with billing and vendor management; experience working with bookkeepers and financial teams.
• Familiarity with Lightspeed POS, Shopify, and Google Workspace is strongly preferred.
• Excellent written and verbal communication skills, with the ability to clearly document processes and policies.
• Highly organized with the ability to manage many moving parts across departments.
• Proven problem-solving abilities and a proactive, can-do attitude.
• Strong discretion, professionalism, and integrity when dealing with confidential information.
• Ability to work independently and collaborate across diverse teams.

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