Chief Operating Officer

Position Overview

Book My Group is seeking a Chief Operating Officer to strengthen the company’s organizational structure and lead its next stage of development. Reporting directly to the President, the COO will translate company priorities into clear responsibilities, consistent processes, and coordinated execution in pursuit of sustainable growth.

This leader will oversee an organizational restructuring designed to create long-term sustainability, improve collaboration, and reduce reliance on individual knowledge and informal ways of working. The COO will serve as a key bridge between accounting and the sales team, manage the relationship with the outsourced HR provider, coordinate closely with the in-house accounting team, and lead the evaluation, implementation, and adoption of technology across the company.

Beyond the initial restructuring, the COO will lead day-to-day operations, maintain accountability for operational performance, and continually improve the company’s systems and processes. This role will ensure the organization has the capacity, coordination, and leadership needed to deliver consistent service and support profitable growth.

Key Responsibilities

Organizational Structure and Leadership

• Partner with the company owners and advisor to assess the current organization and develop a structure that supports the company’s goals.
• Lead restructuring efforts, including clarifying roles, reporting relationships, decision-making authority, and accountability.
• Provide ongoing leadership, coaching, and performance management to the Director of Operations and other direct reports.
• Establish and maintain a consistent rhythm of leadership meetings, departmental coordination, and performance reviews.
• Translate company goals into annual operating plans and quarterly priorities with clear management, timelines, and measures of success.
• Monitor progress, address barriers, and adjust priorities with the President as business needs change.
• Build continuity through documented responsibilities, cross-training, and succession planning.

Process Development and Operational Management along with Growth Opportunities

• Evaluate current workflows, identify gaps, and establish clear, repeatable processes across departments.
• Develop standard operating procedures and define ownership for each major process.
• Improve handoffs between sales, account management, operations, and accounting.
• Oversee day-to-day operational performance, balancing workload, staffing, and resources to meet company commitments.
• Establish meaningful performance measures, review results regularly, and lead corrective action when expectations are not met.
• Ensure processes are understood, followed, and updated as the business evolves.
• Maintain consistent service standards and work with sales and operations to ensure customer commitments align with the company’s capacity to deliver.

Accounting and Sales Coordination

• Serve as the primary operational liaison between the accounting team and other departments.
• Connect accounting requirements with sales activities so information is accurate, complete, and delivered on time.
• Establish clear procedures for communicating bookings, pricing, payment terms, changes, and other information affecting financial reporting.
• Maintain shared visibility into bookings, revenue, payment status, and operational commitments.
• Coordinate with sales leadership and accounting to resolve discrepancies and improve visibility into financial performance.
• Partner with the President and accounting team to develop operating budgets, review results, and address operational issues affecting profitability, cash flow, and efficiency.
• Ensure leadership receives timely financial information and that relevant findings lead to operational action.

Human Resources Coordination

• Manage the relationship with the outsourced HR provider and coordinate the company’s internal HR needs.
• Work with HR and department leaders on recruiting, onboarding, role descriptions, performance management, and employee development.
• Support consistent communication and implementation of company policies.
• Partner with HR to guide employees through organizational changes and reinforce clear expectations.
• Regularly assess staffing needs and management capacity to support business continuity and growth.

Technology Evaluation, Implementation, and Training

• Assess existing technology, its effectiveness, and how consistently it is being used.
• Investigate new systems based on business needs, integration requirements, cost, and expected benefits.
• Lead implementation projects, including vendor coordination, timelines, data migration, testing, and rollout.
• Develop training, documentation, and ongoing support so employees can use systems effectively.
• Establish system ownership and evaluate whether technology investments deliver the intended results.
• Monitor ongoing adoption, data quality, and system performance, addressing issues and coordinating improvements as needed.
• Integrate AI as a tool for the organization in terms of efficiency and growth

Qualifications and Experience

• Senior leadership experience in operations, organizational and business development, or business transformation through acquisition of other businesses or internal growth.
• Demonstrated success building processes, leading organizational change, and sustaining operational improvements.
• Experience translating strategic goals into operating plans and managing teams against measurable results.
• Strong financial understanding and experience coordinating between accounting and revenue-producing teams.
• Experience working with in-house accounting teams and managing outsourced HR or other professional service providers.
• Proven ability to evaluate technology and lead implementation and employee adoption.
• Strong communication, project management, and people leadership skills.
• Travel, hospitality, or group services experience preferred.

What Success Looks Like

• A clear organizational structure with defined responsibilities and accountability.
• Strong coordination between sales, operations, and accounting.
• Documented processes that support consistent execution and business continuity.
• Operating priorities that are actively managed, with measurable progress and timely resolution of issues.
• Managers and employees who understand expectations and receive the support needed to meet them.
• Technology that employees understand and use consistently and effectively.
• Consistent customer service supported by appropriate staffing, systems, and resources.
• A company that can sustain performance and grow with less dependence on the President’s daily involvement.
• Structuring of the organization leading to improved profitability and sustained growth

Pay: From $110,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Paid time off
• Retirement plan

Work Location: Remote