Regional manager - leisure & all inclusive - full-time | remote

The Staff Pad has partnered with a rapidly growing travel and hospitality organization to identify a high-performing Regional Manager – Leisure & All-Inclusive. This key leadership role will serve as the day-to-day leader and primary point of contact for the North American Leisure & All-Inclusive teams, driving sales growth, strengthening partner engagement, and supporting continued success across the organization’s portfolio of brands.

As a remote leadership role, the Regional Manager – Leisure & All-Inclusive will recruit, develop, coach, and motivate a geographically dispersed team while driving performance against business objectives and strategic goals. The role will oversee team performance, resource allocation, partner engagement, and reporting while building strong relationships with Hilton’s preferred wholesale partners and key stakeholders.

Reporting to the Global Director and Executive Director, as a Regional manager the primary focus is to drive sales, educate travel advisors, and strengthen the organization’s presence in the Leisure and All-Inclusive segment across the U.S. and Canada. The position requires occasional domestic and international travel for customer meetings, industry events, conferences, FAM trips, team meetings, and other business activities.

Schedule: Full-Time | Remote

What You’ll Do

Key Responsibility Areas

• Team Management / Admin
• Recruit, onboard, train, coach, and develop a high-performing, geographically dispersed team following the organization’s standard process
• Conduct weekly & monthly 1:1s with North America U.S. and Canada Leisure and All-Inclusive team members to address questions, call files reviews, agencies, and objectives
• Hold weekly 1:1s with the Global Managing Director & Sales team, to review performance, priorities, challenges, opportunities, and development needs
• Facilitate team meetings to communicate priorities, share best practices, recognize achievements, and maintain engagement
• Lead advisor engagement and education initiatives, including FAMs, webinars, training, and TAConnect
• Submit weekly team updates and highlights through Salesforce and ensure team proficiency in Salesforce and MicroStrategy for performance tracking and reporting
• Coordinate monthly TAConnect webinars and ensure consistent team utilization
• Monitor team performance and ensure timely completion of updates, documentation, and quarterly achievements
• Conduct performance reviews and provide ongoing feedback, coaching, and development support
• Maintain accurate Outlook and Microsoft Teams calendars reflecting customer engagement activities
• Monitor team performance and ensure monthly objectives, including calls, meetings, events, training, webinars, and FAMs, are met
• Track team activities in ACNH, Lunch & Learn Reconciliation, and other required trackers
• Manage team expenses, approve claims, and resolve discrepancies before submission to HQ
• Coordinate the success of the HFS FAM Playbook and record outcomes
• Maintain All-Inclusive team call files to ensure effective deployment across high-performing accounts
• Provide ad hoc reports on team activities and performance to the Global Managing Director
• Attend occasional in-person travel advisor engagement events

Analytical & Commercial Responsibilities

• Investigate performance issues, conduct audits, and implement corrective actions with leadership and HR as needed
• Evaluate individual performance through Salesforce and assess the commercial effectiveness of resource deployment
• Optimize team resources and ensure consistent engagement with wholesale partners and agencies
• Analyze market trends, competition, and customer insights to identify growth opportunities
• Expand partnerships, strengthen engagement, and increase awareness of organization’s portfolio of brands

Additional Responsibilities

• Maintain professional business attire for customer-facing events and internal meetings
• Work additional hours and support reasonable ad hoc duties as needed
• Comply with organization requirements for company equipment

What We Are Looking For

Experience and Qualifications

• 5+ years of leadership experience in hospitality or travel, preferably in sales, marketing, or business development
• Knowledge of leisure, resort, and all-inclusive segments preferred
• Experience leading and developing teams of 7+ employees across multiple markets or time zones
• Experience with Salesforce, MicroStrategy, or similar CRM/reporting tools

Additional Skills and Attributes

• Proven ability to manage performance, drive accountability, and achieve KPIs
• Ability to lead change, adopt new tools, and maintain team engagement
• Strong analytical, communication, presentation, and negotiation skills
• Proven ability to build and maintain relationships with stakeholders at all levels
• Highly organized with strong project management and administrative skills
• Proficiency in Microsoft Office, Teams, WebEx, and Zoom
• Self-motivated, professional, adaptable, and willing to support extended hours and additional responsibilities

If you are a strategic and results-driven leader who thrives on building strong teams, developing valuable partnerships, and creating meaningful growth opportunities, this is an exciting opportunity to make an impact across a dynamic North American market. Bring your leadership, commercial expertise, and passion for travel to a role where your work will directly influence team success and long-term business growth. Apply today!