Regional Manager, Leisure & All-Inclusive (Hotel Sales)

About the Role

We are seeking an experienced, results-driven Regional Manager - Leisure & All-Inclusive, North America to lead a geographically dispersed sales team responsible for driving sales growth, partner engagement, and portfolio awareness across the United States and Canada.

This role serves as the day-to-day leader and primary point of contact for the North America Leisure & All-Inclusive team, with responsibility for team development, commercial performance, partner engagement, resource deployment, reporting accuracy, and execution of strategic business priorities.

The successful candidate will be an experienced sales leader who can establish clear expectations, create accountability, develop talent, implement effective processes, and build a collaborative and highly engaged remote team. The Regional Manager will also play an important role in strengthening relationships with travel advisors, wholesale partners, host agencies, consortia, and other key stakeholders to maximize commercial opportunities across the leisure and all-inclusive segments.

This position is fully remote and requires approximately 20% travel, including domestic and occasional international travel, to support customer meetings, industry events, conferences, familiarization (FAM) trips, team meetings, and field coaching. Additional travel may be required during onboarding to shadow team members and develop familiarity with key partners, accounts, and markets.

Key Responsibilities

Team Leadeship & Development

• Lead, coach, motivate, and develop a geographically dispersed team across the United States and Canada.
• Foster a culture of collaboration, accountability, engagement, open communication, and high performance.
• Recruit, onboard, train, and develop team members in accordance with established processes and expectations.
• Conduct regular 1:1 meetings, account and territory reviews, performance discussions, and career development conversations.
• Establish clear individual and team objectives and monitor performance against goals, KPIs, deadlines, and established standards.
• Conduct formal performance reviews and provide ongoing coaching, constructive feedback, development planning, and performance support.
• Support team members in developing confidence, ownership, and independence within their respective roles.
• Facilitate regular team meetings to communicate business priorities, share best practices, address challenges, and recognize achievements.
• Ensure team adherence to applicable company policies, HR requirements, reporting standards, and operational procedures.
• Partner with leadership to identify development opportunities and support long-term talent and succession planning.

Sales Leadership & Business Growth

• Lead execution of regional sales strategies designed to achieve commercial objectives and expand market presence across the leisure and all-inclusive segments.
• Drive achievement of regional sales goals, business objectives, and key performance indicators.
• Develop and strengthen relationships with preferred wholesale partners, travel advisors, host agencies, consortia, and other key industry stakeholders.
• Coach and support team members in the field through customer visits, partner meetings, trade events, industry conferences, and other sales engagements.
• Ensure sales resources are appropriately deployed across high-potential accounts, partners, markets, and commercial opportunities.
• Identify opportunities to expand existing partnerships, increase engagement, strengthen advocacy, and grow share of business.
• Support travel-advisor education and engagement initiatives, including webinars, learning programs, training sessions, videos, FAM trips, and promotional campaigns.
• Collaborate with internal stakeholders to ensure regional sales activities remain aligned with broader commercial priorities.

Operational Excellence & Process Management

• Develop, implement, and maintain effective sales processes and procedures that support operational consistency and team success.
• Ensure accurate and timely reporting through Salesforce, MicroStrategy, and other applicable business systems.
• Monitor team activity, account coverage, resource deployment, and customer engagement to maximize effectiveness.
• Oversee monthly and quarterly reporting, team updates, activity tracking, and business reviews.
• Manage travel-advisor education projects, webinars, training initiatives, and strategic engagement programs.
• Maintain visibility of team calendars, travel schedules, and customer-facing activities.
• Ensure deadlines, deliverables, reporting requirements, and performance objectives are met accurately and on time.
• Identify process inefficiencies and opportunities to improve team productivity, consistency, and overall operational effectiveness.
• Promote adoption and consistent use of established processes, systems, and tools across the team.

Performance & Commercial Analysis

• Analyze individual and team performance using CRM, reporting, and commercial data to identify trends, opportunities, and areas requiring additional focus.
• Evaluate account coverage and resource deployment to ensure team efforts are aligned with commercial opportunity.
• Analyze customer insights, market trends, competitive activity, and partner performance to identify opportunities for growth.
• Use data and commercial insights to guide regional priorities, account strategies, coaching, and resource allocation.
• Identify performance challenges and implement appropriate coaching, development, or corrective actions in collaboration with relevant stakeholders.
• Provide leadership with regular performance updates, commercial insights, and recommendations to support informed business decisions.

Financial & Business Management

• Manage team budgets, business expenses, and applicable partner investment activities.
• Review and approve expense submissions while ensuring accuracy and adherence to established policies and budget expectations.
• Monitor spending and resource allocation to ensure responsible and effective use of available budgets.
• Support planning and forecasting of team expenses and business requirements.
• Provide leadership with relevant financial, activity, and performance reporting as required.

Administrative Responsibilities

• Maintain accurate personal and team calendars reflecting customer meetings, events, travel, and other business activities.
• Ensure required sales activities, partner engagements, and team initiatives are accurately documented in applicable systems.
• Maintain strong organization and follow-through across multiple projects, priorities, stakeholders, and deadlines.
• Work effectively from a remote home-office environment while leading employees across multiple markets and time zones.
• Maintain a high level of professionalism and accountability in internal and external interactions.
• Demonstrate flexibility to work non-standard hours and undertake reasonable additional responsibilities based on business needs.

Skills & Qualifications

Required

• 5+ years of leadership experience, preferably within hospitality, travel, tourism, sales, or a related industry.
• Proven experience leading and developing field-based sales teams and driving results against established sales targets and business objectives.
• Experience managing remote employees across multiple territories, markets, and/or time zones.
• Demonstrated ability to establish clear expectations, create effective processes, drive accountability, and improve operational effectiveness.
• Strong coaching and people-development capabilities, with experience supporting sales professionals with different strengths, responsibilities, and development needs.
• Strong commercial acumen and analytical skills, with the ability to interpret data and translate insights into actionable business strategies.
• Strong organizational and project-management skills with the ability to manage multiple priorities, stakeholders, and deadlines simultaneously.
• Excellent verbal, written, presentation, and relationship-building skills.
• Demonstrated ability to build productive relationships with internal stakeholders, customers, and external business partners.
• Experience utilizing CRM and reporting systems, preferably Salesforce.
• Proficiency with Microsoft Office, Microsoft Teams, Zoom, WebEx, and similar business productivity and communication tools.
• Ability to travel approximately 20%+, including domestic and occasional international travel.
• Ability to work effectively and independently in a remote leadership environment.

Preferred

• Hospitality industry experience with a major hotel company, resort organization, travel supplier, tour operator, destination management company, or wholesale travel organization.
• Knowledge of the leisure, resort, and all-inclusive hospitality segments.
• Experience working with travel advisors, host agencies, consortia, and wholesale travel partners.
• Experience with business intelligence and sales analytics platforms such as MicroStrategy.
• Experience managing budgets, forecasting expenses, and optimizing resource allocation.
• Experience supporting or leading sales teams across the United States and Canada.

Benefits

• Paid Time Off (PTO)
• 401(k) with 3% employer match (after probationary period)
• Fully employer-paid medical, dental, and vision insurance for the employee
• Mobile phone allowance