Assistant General Manager

Help Shape the Future of a Resort with a Fresh Perspective

Vacation Village at Berkshires is excited to introduce a newly created Assistant General Manager position designed to strengthen our leadership team and elevate the resort experience for our owners and guests.

This isn't a role for someone who prefers to manage from behind a desk. We're looking for a hands-on, adaptable leader who enjoys being visible, solving problems in real time, supporting multiple departments, and bringing new ideas that improve operations and the guest experience.

Working alongside the General Manager, you'll help drive day-to-day resort operations, build accountability across teams, and create a culture where employees are engaged and guests feel genuinely cared for. If you thrive in a dynamic environment where every day is different, we'd love to meet you.
What You'll Do

• Partner with the General Manager to oversee the daily operations of the resort while providing leadership across multiple departments.
• Lead by example with a visible, hands-on leadership style that supports associates and enhances the guest experience.
• Bring a fresh perspective by identifying opportunities to improve processes, strengthen teamwork, and increase operational efficiency.
• Coach, develop, and inspire team members through regular communication, performance feedback, and daily engagement.
• Support resort operations across Front Desk, Housekeeping, Maintenance, and other departments based on business needs.
• Conduct daily property inspections to ensure the resort is clean, safe, well-maintained, and guest-ready.
• Assist with preventive maintenance programs, renovation projects, and capital improvements while coordinating with vendors and contractors.
• Help manage operational budgets and departmental expenses to achieve financial goals.
• Resolve guest and owner concerns with professionalism, urgency, and a hospitality-first mindset.
• Ensure compliance with company standards, safety regulations, and operational procedures.
• Build collaborative relationships with resort leadership, associates, vendors, and HOA partners.

What We're Looking For

• 4+ years of progressive leadership experience in resort, hotel, or timeshare operations.
• A hands-on leadership style with the flexibility to jump in wherever needed.
• Strong operational knowledge across multiple resort departments, including guest services, housekeeping, and/or facilities.
• Experience leading teams through change while building accountability and engagement.
• Excellent communication, coaching, and problem-solving skills.
• Experience managing vendors, projects, and property improvements is highly preferred.
• Bachelor's degree in Hospitality Management, Business Administration, or a related field preferred (or equivalent experience).

Why Join Vacation Village at Berkshires?

• Be part of a newly created leadership role with the opportunity to make a lasting impact.
• Help shape the future of resort operations by bringing fresh ideas and innovative solutions.
• Work alongside an experienced leadership team that values collaboration, accountability, and continuous improvement.
• Build meaningful relationships with associates, owners, and guests while creating memorable vacation experiences.
• Grow your hospitality career with a company committed to developing its leaders.

If you're an adaptable hospitality leader who enjoys rolling up your sleeves, inspiring teams, and making a visible impact every day, we'd love to hear from you.

Apply today and help shape the future of Vacation Village at Berkshires.