Regional Sales Manager - Midwest

Pleasant Holidays is seeking a dynamic, relationship-focused Regional Sales Manager, to drive revenue growth through meaningful advisor engagement and development of strong agency partnerships in the Midwest Region. Territory currently includes IL, MN, MI, IN, OH, KY, MO, WI, ND, SD and KS but subject to change depending on the needs of the business. Candidate must reside within the assigned territory (Chicagoland preferred).

Reporting to the Head of Sales – Pleasant Holidays, this role is the “face of the brand” in the territory and serves as the key driver of sales growth, as well as the main relationship manager between travel advisors, agencies and the company. The Regional Sales Manager provides consistent advisor engagement, customized business plan execution with agency accounts, education, and measurable revenue growth.

The ideal candidate understands premium and luxury land travel, the tour operator business model, and consultative sales. This individual is highly organized, builds trusted relationships, follows through on commitments and is motivated by helping travel advisors grow their businesses through the products, service, and support of a trusted tour operator partner. This individual is also highly collaborative, and supportive of colleagues and the overall company objectives across our brands.

Key Responsibilities

Territory Planning and Account Management

• Strategic Approach. Develop a territory Strategy and be able to execute on the plan. Segment accounts by opportunity and focus on high opportunity advisor engagement, business development, training, marketing, and follow-up activity.
• Manage assigned relationships. Develop and grow a portfolio of high-value advisor relationships within designated territory while supporting established account-level revenue objectives.
• Organization and disciplined follow-through. Maintain clear action plans, timelines, ownership, and progress updates for assigned initiatives.

Advisor Engagement & Business Development

• Seek out and develop new opportunities: Engage top-producing, emerging, lapsed, and high-opportunity advisors to improve activation, retention, product adoption, and sales growth.
• Build trusted partnerships. Maintain a proactive cadence of virtual and in-person meetings, business reviews, consultations, and timely follow-up both with new and established accounts.
• Convert opportunity into growth. Identify business opportunities and execute tailored action plans that support profitable revenue growth.
• Provide responsive support. Provide professional, solution-focused assistance and coordinate with internal teams to strengthen advisor satisfaction and long-term loyalty.
• Deliver advisor education. Lead customized virtual and in-person training, webinars, office hours, and onboarding initiatives that increase advisor confidence and selling capability.
• Lead purposeful educational journeys. Plan, coordinate, and host domestic and international Educational Journeys (familiarization trips) aligned with advisor development and revenue objectives; ensure strong post-FAM follow-up.

Performance, Insights & Collaboration

• Deliver measurable results. Meet or exceed assigned revenue, advisor engagement, and business development objectives.
• Use data to prioritize. Leverage CRM, reporting, AI tools and analytics to monitor performance, document activity, identify gaps, and focus effort on the highest-opportunity advisors.
• Share market intelligence. Monitor competitor activity, advisor sentiment, and premium and luxury travel trends; provide actionable insights and partner feedback to leadership.
• Collaborate cross-functionally. Work closely with Sales, Marketing, Product, Training, Operations, Reservations, Customer Experience, and other teams to execute account priorities. Collaborate with colleagues from other company brands to drive success across all brands.
• Support organizational priorities. Participate in company initiatives and special projects that advance broader business objectives. Support colleagues with cross-territory coverage as needed. Other duties as assigned.

Success Measures

Success in this role will be measured through a balanced set of revenue, engagement, collaboration and execution indicators, including:

• Revenue performance and progress against assigned objectives
• Territory strategy development and execution
• Advisor activation, re-engagement, retention, and growth
• Advisor meetings, business reviews, in-person visits, trainings, and follow-ups completed
• Customized business plans, campaigns, promotions, and FAM strategies executed
• Participation and business outcomes from webinars, events, and advisor programs
• Quality, timeliness, and accuracy of activity and performance reporting
• Advisor satisfaction, partner feedback, and cross-functional execution

Qualifications & Experience

We are seeking an accomplished sales professional who brings:

• Bachelor's degree or equivalent professional experience.
• Minimum of five years of experience in sales, partnership development, account management, or another client-facing role.
• Travel industry experience strongly preferred; experience with Host Agencies, Consortia, travel advisors, hospitality partners, or premium and luxury consumer markets is highly valued.
• Strong understanding of premium and luxury land travel and the travel advisor distribution channel.
• Demonstrated success in consultative selling, relationship development, strategy execution, business planning, and revenue growth.
• Experience delivering presentations, webinars, training, and advisor-facing events.
• Confidence analyzing sales data and using CRM and reporting tools to guide priorities and performance.
• Excellent written, verbal, presentation, and active-listening skills.
• Familiarity and ability with digital tools, including MS Office, Social Media and AI
• Strong organization, project management, accountability, and follow-through.
• A polished professional presence and genuine passion for travel.
• Ability and willingness to travel up to 60%, including air and ground travel for partner meetings, conferences, events, and educational trips.
• Valid passport
• Residence within the assigned territory and in close proximity to a major international airport (Chicagoland preferred)
• Eligibility for enrollment in the company's AAA Safe Driving Program.

Core Competencies

Relationship Building | Consultative Selling | Travel Advisor Engagement | Business Plan Execution | Revenue Growth | Data-Driven Decision-Making | Collaboration | Accountability | Adaptability | Presentation Skills | Organization

Compensation & Opportunity

The Regional Sales Manager, Strategic Accounts participates in a base salary plus incentive compensation program with unlimited earning potential based on the achievement of defined corporate financial objectives and individual business goals for Pleasant Holidays.

Ready to elevate the world of travel? We'd love to meet you.

Benefits to working at Pleasant Holidays:
•    Medical (with prescription)
•    Vision
•    Dental
•    Flexible Spending Accounts
•    Paid Time Off for Holidays, Vacation, and Illness
•    Company paid Life Insurance
•    Long Term Disability
•    401(k) Plan
•    AFLAC Plans
•    Travel Discounts on all Pleasant Holidays packages, Hotel Rooms, Car Rentals, Tours & Activities. Discounts apply to family members and friends too!