Osthoff Leadership Program

The Osthoff Resort; Elkhart Lake (WI); On-site; USD 23,000 - 32,000; Full time

Benefits offered by this job

Medical Insurance

Dental Insurance

Vision Insurance

401k with company match

Paid vacation/PTO

Resort-wide discounts

Job summary

The Osthoff Resort in Elkhart Lake, Wisconsin, invites you to join the Osthoff Leadership Program. Through hands-on rotations across Front Desk, Housekeeping, Maintenance/Grounds, Restaurants, Events, Spa, Sales, and more, you’ll gain comprehensive resort operations exposure and leadership mentorship.

Starting at $20 per hour, the program runs 6–9 months with a formal sponsor structure and potential placement into an operations or guest experience leadership role based on performance.

Qualifications

• High School Diploma is required.
• Previous hospitality, restaurant, customer service, or leadership experience preferred.
• Strong interest in building a career in hospitality operations.
• Positive attitude and willingness to learn.
• Strong communication and interpersonal skills.
• Ability to work well in a fast-paced team environment.
• Must be flexible and willing to work a variety of shifts, including evenings, weekends, and holidays.

Responsibilities

• Learn core workflows, service standards, and the why behind each department's priorities.
• Support real work, contributing to team outcomes.
• Complete rotation deliverables that demonstrate learning and value.
• Identify operational challenges and opportunities for improvement.
• Maintain professionalism, confidentiality, and a guest-first mindset.

Skills

Strong communication

Interpersonal skills

Teamwork

Willingness to learn

Flexibility

Education

High School Diploma

Job description

The Osthoff Resort & Spa Leadership Program

Are you passionate about hospitality, creating exceptional guest experiences, and taking on new challenges? Are you looking to build a career in hospitality and develop the skills needed to become a future leader?

The Osthoff Resort & Spa is looking for the next candidate for our Osthoff Leadership Program! Through a structured rotational experience, participants will work alongside experienced leaders, contribute to daily operations, and gain a well-rounded understanding of how a full-service resort operates. The program provides hands-on exposure to key departments, building a comprehensive understanding of resort operations while identifying the best long-term fit for both the participant and the resort.

ProgramGoals

Develop future resort leaders in hospitality operations and guest experience.

Build cross-departmental knowledge to improve collaboration and operational decision-making.

ProgramStructure

• Duration:6-9 months
• Schedule:Full-time, schedule varies by department needs and peak periods. Candidates must be flexible.
• Rotation Length:varies by department (tailored as needed)
• Rotations may include, but are not limited to: Front Desk/Guest Services, Housekeeping, Maintenance/Grounds, Restaurants, Events/Banquets, Aspira Spa, Sales/Marketing, etc.
• Reporting: The Leadership Program candidate will have an assigned executive sponsor who they report to. Departmental managers will be assigned as mentors for each department rotation.
• Upon completion: Successful completion of the Leadership Programmay potentially lead to placement into an operations or guest experience leadership role based on organizational needs, performance, and participant interests. Placement within the organization after completion of the program is not guaranteed.

Participant Responsibilities

During each rotation, the participant will:

Learn core workflows, service standards, and the "why" behind each department's priorities.

Support real work (not observation-only), contributing to team outcomes.

Complete rotation deliverables that demonstrate learning and value.

Identify operational challenges and opportunities for improvement.

Maintain professionalism, confidentiality, and a guest-first mindset.

Rotation includes:

• Clear Objectives: Defined learning and performance goals for the rotation.
• Department Mentor: A designated manager to provide guidance, coaching, and feedback.
• Hands-on Experience: Active participation in daily departmental operations.
• Operational Recap: Observations/ reporting recap of the participant’s experience, including best practices, key takeaways, challenges, and potential opportunities for improvement.
• Performance Evaluation: Feedback from the department mentor and leadership regarding performance, development, and readiness for increased responsibility.

Candidate Qualifications

• High School Diploma
• Previous hospitality, restaurant, customer service, or leadership experience preferred
• Strong interest in building a career in hospitality operations
• Positive attitude and willingness to learn
• Strong communication and interpersonal skills
• Ability to work well in a fast-paced team environment
• Ability to take direction, accept feedback, and take on new challenges
• Must be flexible and willing to work a variety of shifts, including evenings, weekends, and holidays

The participant will start at $20 an hour, paid on a bi-weekly basis, subject to deductions for taxes and other withholdings as required by law or the policies of the company. The participant will be eligible for medical, dental, and vision insurance, disability/life insurance, 401k plus company match, paid vacation/PTO and resort-wide discounts.

The chosen candidate must be able to start the program on Monday, November 9th, 2026.

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Why Work at the Osthoff Resort?

At The Osthoff Resort & Spa, we believe exceptional guest experiences start with an exceptional team. We foster a supportive, welcoming culture where employees are valued, encouraged, and empowered to grow. Team members enjoy competitive pay and a comprehensive benefits package, including paid time off, medical, dental, and vision insurance, a 401(k) with company match, resort-wide discounts, and more. Flexible scheduling and opportunities for advancement make it easy to build a rewarding career while maintaining balance. Here at The Osthoff, you're more than an employee—you’re part of a team that takes pride in creating memorable experiences for our guests.

The Osthoff Resort is an Equal Employment Opportunity Employer.

About Us

Located in the charming lakeside village of Elkhart Lake, The Osthoff Resort & Spa offers an elevated and inviting atmosphere with world-class accommodation, exceptional dining, and a range of leisure activities. With a focus on personalized service and creating lasting memories, the resort is a cherished destination for those seeking relaxation, adventure, and a true Wisconsin getaway. Surrounded by natural beauty, rich history, and a vibrant sense of community, our team enjoys a setting that feels both inspiring and welcoming year-round. Whether you're seeking professional growth, meaningful connections, or a better quality of life, The Osthoff offers the chance to be part of a respected hospitality team dedicated to creating memorable experiences in an extraordinary location.