Sales Strategy Jobs in Wisconsin (NOW HIRING)

COMPANY SUMMARY

At Holiday Vacations, our mission is to enrich lives with valued travel experiences. We offer inclusive guided tours led by professional Tour Directors to more than 80 destinations on six continents. We travel by air, motor coach, trains, and cruises on itineraries that bring the destination alive for our guests. We are headquartered in Eau Claire, Wisconsin, and are a subsidiary of Xanterra Travel Collection, the largest national park concessionaire in the U.S. Xanterra also owns other tour operator and cruise line brands including VBT Bicycling Vacations, Country Walkers, and Windstar Cruises.

POSITION SUMMARY

The Director of Sales provides department leadership and strategic oversight for Holiday Vacations' salesdriven demand channels, including media partnerships, group sales, and Friends & Family programs. This role owns the full lifecycle of sales partnerships and programs - from strategy and planning through execution and performance management - and serves as the primary bridge between Sales and internal partners across Marketing, Guest Travel, Operations, Inventory, Tour Sales, and Leadership.

This position partners with the VP of Sales & Marketing  to set the annual sales strategy and revenue objectives; establishes standards and processes; ensures operational readiness and execution discipline; and leads a team of Sales Managers and Coordinators. The role blends strategic leadership, revenue accountability, operational problemsolving, and people development to drive sustainable growth and strong guest outcomes.

WELCOME TO "THE HV WAY" - At Holiday Vacations, how we work is just as important as what we deliver.

• Honesty & Integrity: We act with honesty and accountability, building trust with every guest, partner, and teammate. We keep our promises.
• Create Community: We create community by treating each other and our guests like extended family, fostering belonging, celebrating, and supporting one another.
• Surprise & Delight: We go beyond expectations to create meaningful experiences. We make every effort to exceed expectations.
• Grow Together: We embrace curiosity, feedback, and continuous learning - always striving to be better and do better.
• Innovate Boldly: We seek fresh ideas, adapt to change, and look for ways to stay ahead in a dynamic travel landscape
• Protect What Matters: We prioritize safety and sustainability for our people, our guests, and the places we explore.

CORE COMPETENCIES

• Celebrate the Team: We succeed together, value each person's gifts and contributions, and take time to enjoy the journey along the way.
• Strategic Sales Leadership: Proven ability to set sales vision, strategy, and priorities across multiple demand channels while translating growth objectives into clear, executable plans.
• Leadership & Collaboration: Proven ability to lead teams, build alignment, and collaborate effectively across functions to drive shared accountability and results.
• Entrepreneurial & Growth Mindset: Demonstrated ability to identify opportunities, build and scale sales programs, and drive revenue growth in an innovative, fastmoving, and evolving environment.
• Operational Execution & Discipline: Strong ability to translate strategy into disciplined execution through clear processes, performance management, and consistent followthrough.
• Financial Performance Management: Demonstrated ability to set revenue goals, monitor performance against targets, analyze trends, and make informed decisions to drive results while balancing operational and capacity considerations.

AREAS OF RESPONSIBILITY

People Leadership & Team Development

• Build and sustain a high trust, accountable, and collaborative sales team culture.
• Lead, coach, and develop Sales Managers and Coordinators through clear goal setting, regular check ins, and structured performance management.
• Set expectations, delegate responsibilities effectively, and monitor performance to ensure consistent execution and results.
• Provide timely, actionable feedback and conduct formal performance evaluations.
• Support employee growth by identifying development needs and facilitating learning opportunities.
• Ensure teams have the tools, training, and resources needed to perform effectively, using sound judgment and discretion when managing sensitive matters.

Sales Strategy & Portfolio Oversight

• Provide strategic oversight of all sales driven demand channels, including media partnerships, group sales, and Friends & Family programs.
• Partner with the VP of Sales & Marketing to establish annual sales strategy, revenue targets, and priorities aligned with company objectives and inventory capacity.
• Lead the development, execution, and evolution of sales programs and partnerships.
• Evaluate new and existing opportunities based on revenue impact, brand alignment, and operational feasibility.
• Serve as escalation point for complex sales, partner, or program execution issues.

Financial Oversight & Performance Management

• Own departmental performance against annual sales, guest volume, and revenue goals.
• Monitor sales results, trends, and execution performance to identify risks and growth opportunities.
• Lead regular performance reviews and use insights to drive accountability and continuous improvement.

CrossFunctional Collaboration

• Partner closely with Marketing, Guest Travel, Operations, Inventory, Tour Sales, and other internal stakeholders to align planning through execution.
• Balance sales objectives with operational realities to support strong guest and business outcomes.

Operational Execution & Process Discipline

• Ensure operational readiness for all sales programs through clear processes, timelines, and accountability.
• Own and maintain sales related standard operating procedures, templates, and workflows.
• Champion continuous improvement in tools, systems, and processes to support scalability and efficiency.

Organizational Leadership & Representation

• Prepare and deliver sales updates, performance insights, and recommendations to leadership.
• Serve as a subject matter expert for sales strategy and execution across the organization.
• Represent Holiday Vacations in partner meetings and external engagements as appropriate.
• Perform other duties as assigned.

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee for this job; tasks and responsibilities may change at any time with or without notice.

KNOWLEDGE, SKILLS, AND EXPERIENCE

• Bachelor's degree in hospitality, travel, business, supply management, or a related field; equivalent experience may be considered.
• Demonstrated experience in sales leadership, partnerships, media, group sales, or a related commercial field.
• Proven ability to provide portfolio level strategic oversight and revenue accountability across multiple sales channels.
• Experience building, scaling, or expanding sales programs, pipelines, or partnerships.
• Demonstrated financial and commercial acumen, including performance analysis and data informed decision making.
• Proven ability to lead and develop managers and teams through goal setting, performance management, and coaching.
• Strong cross functional collaboration skills with the ability to influence outcomes across Marketing, Operations, Inventory, and Sales functions.
• Excellent verbal and written communication skills, with the ability to convey complex information clearly to varied audiences.
• Strong organizational skills with the ability to manage competing priorities, deadlines, and interdependencies.
• Demonstrated ability to exercise sound judgment, discretion, and problem solving in time sensitive and high impact situations.
• Proficiency in Microsoft 365 (Word, Outlook, Teams, PowerPoint); strong Excel skills preferred; experience with CRM, reporting, or sales tracking systems required.
• Ability to adapt to change, lead through ambiguity, and drive execution in an evolving and entrepreneurial environment.

WORKING CONDITIONS AND ARRANGEMENTS

Work Location: The preferred work location is the Holiday Vacations corporate headquarters in Eau Claire, Wisconsin. The office environment may have moderate noise levels from office equipment and verbal interactions.

Schedule: Work hours are during the regular business week, but there may be variations due to the time of year and department demands. This position follows a hybrid work arrangement, involving both in-office and remote work, based on the department's needs. Travel may be required, especially for travel show execution.

Physical Requirements: The job requires the ability to sit for extended periods of time, as well as the ability to frequently walk and lift or carry up to 35 lbs. May require bending, twisting, stooping, grasping, and reaching outward or above shoulders, lift/carry and push or pull up to 50 lbs.

Technical and Home-Office Requirements: Must have a distraction-free workspace/environment with space for a desktop computer with two monitors. Must have a stable power source and internet connection, including a dedicated high-speed internet and ethernet connection. Connection cannot be wireless, Wi-Fi extenders, Wi-Fi repeaters, or hotspots. Ability to plug in your equipment to modem/router during work times.

Benefits: For full-time employees, Holiday Vacations offers a comprehensive benefits package including Medical, Dental & Vision; HSA & FSA; Life & Disability; Accident, Hospital & Critical Illness; Pet Insurance; Paid Time Off and Holiday Paid Time Off; 401(k) with Company Match; Employee Assistance Plan; Education Assistance; and Employee Travel Discounts and Travel Deals.

EEO: Holiday Vacations is committed to a diverse and inclusive workplace. We are an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, pregnancy, genetic information, protected veteran status, or any other legally protected status.