Director of Caddie Services at Sand Valley

Sand Valley is a golf resort and community settled gently upon 12,000 acres of rugged, prehistoric sand dunes in central Wisconsin. Here, residents and guests will find six world-class golf courses built in harmony with the land: Sand Valley, Mammoth Dunes, Sandbox, The Lido, Sedge Valley, and Commons. Founded in 2016 by brothers Michael and Chris Keiser, the resort is known for its friendly hospitality and a community of golf and outdoor enthusiasts who have been drawn to the raw beauty and serenity of the vast Wisconsin Wilderness.

Beyond premier golf, Sand Valley is a year-round celebration of all the outdoors from fat-tire biking, hiking, and kayaking to ice hockey, skating, or a guided cold plunge. The resort now features a 13,000-square-foot Tennis Center with 16 grass tennis courts and the twelfth Court Tennis facility in the United States. Alongside soul-stirring golf and outdoor exploration, Sand Valley offers a variety of savory dining venues showcasing globally inspired and rustic Wisconsin cuisine.

The Sand Valley team works together to create experiences of a lifetime by asking questions and sharing ideas. With authenticity and a hard-working attitude, Sand Valley helps guide guests through an immersive experience in Wisconsin's natural beauty and away from the demands of daily life.

Position Summary

The Director of Caddie Services leads the daily coordination of caddie services across Sand Valley’s six golf courses, providing dependable caddie coverage and an exceptional walking-golf experience. This position forecasts demand, coordinates independent caddie contractor assignments, and leads caddie supervisors, junior caddies, and administrative team members.

The Director partners with Golf Operations and other resort departments to strengthen service standards, respond to guest needs, and improve operations. A central responsibility of this role is to enhance the overall guest experience through positive, professional interactions while fostering the same service-oriented mindset among the caddie team. This position serves as a mentor and leader, helping develop staff who consistently deliver exceptional hospitality and create memorable experiences for every guest.

Essential Duties and Responsibilities

Caddie Operations and Coordination

• Oversee daily caddie operations across all six courses; forecast demand and coordinate contractor availability, loops, tee times, assignments, and supervisory coverage in response to guest itineraries and seasonal volume.
• Coordinate caddie recruitment, screening, orientation, availability, and assignments in keeping with applicable arrangements; separately oversee recruitment, onboarding, training, and retention of junior caddies.
• Maintain accurate systems for scheduling, contractor assignments, communication, evaluations, and program records; establish contingency plans for weather delays, schedule changes, and peak demand.
• Partner with golf shops, reservations, tournaments, and other departments to anticipate group needs and ensure appropriate caddie coverage.

Team Leadership and Guest Experience

• Establish and communicate consistent service expectations for caddie experiences, including professionalism, course knowledge, pace of play, etiquette, equipment care, safety, and guest engagement.
• Lead, coach, and develop caddie supervisors, junior caddies, and administrative team members through training, performance evaluations, feedback, and ongoing development.
• Foster a positive, inclusive, and service-minded environment that encourages teamwork, accountability, development, and retention.
• Monitor guest feedback and caddie service evaluations, address concerns professionally, and implement improvements in partnership with the golf operations team.

Junior Caddie and Evans Scholarship Programs

• Assist with the Junior Caddie Training Program, including recruitment, instruction, practical training, evaluations, mentorship, and progress records.
• Help identify and mentor qualified Evans Scholarship candidates, providing guidance on eligibility, academic expectations, caddie records, and the application process in collaboration with families, schools, and scholarship representatives.

Administration and External Partnerships

• Assist with departmental staffing forecasts, budgets, cost controls, reporting, and operational process improvements.
• Apply company operating and safety policies and co