Head of Operations and Billing

ObjectiveThe 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 ResponsibilitiesOperational Management & Office OversightOwn 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 CoordinationManage 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 & ComplianceServe 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 PartnershipPartner 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 QualificationsBachelor'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.

Created: 2025-09-26