Billing Specialist

The Osthoff Resort; Elkhart Lake (WI); On-site; USD 42,000 - 54,000; Full time

Job summary

The Osthoff Resort in Elkhart Lake, Wisconsin is seeking a Billing Specialist to ensure accurate, timely group billing. You will collaborate with Sales and Accounting to manage charges, deposits, and payments, while maintaining detailed AR records and confidential information.

The role requires strong organizational, mathematical, and communication skills, with proficiency in Excel and Word. Prior resort/hotel experience is a plus, and a high school diploma is required with a preference for

Qualifications

• High School Diploma required; Associate or Bachelor’s degree preferred in Accounting, Business Administration, or related field.
• Minimum of two years clerical/administrative experience including at least one year as admin or executive assistant in a fast-paced office.
• Proficiency in Microsoft Office (Excel and Word); working knowledge of basic accounting and accounts receivable principles.

Responsibilities

• Create, review, and process invoices for group business and related resort activities in a timely, accurate manner.
• Coordinate with Sales to understand upcoming groups, contracts, activities, and billing needs.
• Review billing information and supporting docs to ensure charges are correct before invoicing.
• Maintain clear communication between Sales and Accounting on billing needs, changes, discrepancies, and missing information.
• Record payments in AR system and maintain accurate AR records.
• Create invoices and billing materials to be sent to customers.
• Reconcile pickup forms and settlements after group departures.
• Collect deposits, tax-exempt forms, and S211 forms for groups and distribute accordingly.
• Help investigate disputed charges and resolve discrepancies.
• Reconcile assigned accounts to General Ledger monthly.
• Maintain organized billing documentation and records; ensure confidentiality.
• Communicate professionally with clients regarding invoices and payments.
• Identify opportunities to improve billing accuracy and interdepartmental communication.
• Support resort values, mission, and culture; assist with invoice entry and other accounting tasks as needed.
• Perform other duties as assigned by resort leaders.

Skills

Organizational skills

Mathematical skills

Communication skills

Problem-solving

Education

High School Diploma

Associate or Bachelor's degree preferred

Tools

Excel

Word

Job description

The Billing Specialist is responsible for ensuring accurate and timely billing for group business at The Osthoff Resort. This position works closely with both the Sales and Accounting departments to ensure group arrangements, activities, charges, payments, and billing details are properly communicated, documented, and processed.

Serving as an important connection between Sales and Accounting, the Billing Specialist reviews group billing information, prepares invoices, maintains accounts receivable records, and assists in resolving billing discrepancies. The ideal candidate is highly organized, detail-oriented, comfortable working with numbers, and committed to providing exceptional internal and external customer service.

Duties and Responsibilities

• Create, review, and process invoices for group business and related resort activities in an accurate and timely manner
• Work closely with the Sales team to understand upcoming groups, contracted arrangements, activities, and billing requirements
• Review group billing information and supporting documentation to help ensure charges are accurate and complete before final invoicing
• Maintain clear communication between Sales and Accounting regarding group billing needs, changes, discrepancies, and outstanding information
• Record payments in the accounts receivable system and maintain accurate A/R records
• Creating invoices and billing materials to be sent directly to the customer
• Complete pickup forms and reconcile pickup after group’s departure
• Collect deposits, tax exempt forms, and S211 Forms for groups and distribute accordingly
• Assist with researching and resolving disputed or questioned charges
• Reconcile assigned accounts to the General Ledger monthly
• Maintain accurate, organized, and complete billing documentation and records
• Communicate professionally and promptly with clients regarding invoices, payments, and billing questions
• Maintain confidentiality when handling financial, guest, and business information
• Identify opportunities to improve the accuracy and efficiency of billing processes and communication between departments and clients
• Support and promote the resort’s values, mission, vision, and culture
• Assist with invoice entry and other Accounting functions as needed
• Other duties as assigned by resort leaders

Qualifications

• Education: High School Diploma. Associate or bachelor’s degree in Accounting, Business Administration, or a related field preferred
• Experience: Prefer a minimum of two years of clerical/administrative experience that includes at least one year of administrative assistant or executive assistant role in a fast-paced professional office. Resort/hotel experience is a plus
• Skills: Strong organizational, mathematical, communication, and problem-solving skills. Proficiency in Microsoft Office, particularly Excel and Word. Working knowledge of basic accounting and accounts receivable principles
• Attributes: Highly detail-oriented, accurate, organized, and capable of managing multiple priorities. Must possess a positive attitude and a collaborative, solution-oriented approach
• Strong interpersonal and guest-service skills and the ability to work effectively with all resort departments and clients
• Ability to work independently while contributing positively within a team environment
• Professional written and verbal communication skills
• Ability to handle financial and confidential information with discretion
• Flexibility to meet the business needs of the department and organization
• Ability to learn quickly and accurately

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.