Regional Sales Manager - Luxury, Midwest

Brand: EVOKE | INSPIRE

EVOKE | INSPIRE is seeking a dynamic and relationship-driven Regional Sales Manager, Luxury to serve as a key ambassador for our brand and drive strategic growth through meaningful partnerships with luxury travel advisors across a defined region. This role is central to our expansion within the high-end travel market, with a focus on cultivating trust, driving revenue, and deepening engagement with elite agency partners.

The ideal candidate possesses a refined understanding of luxury travel, a consultative sales approach, and a passion for creating unforgettable travel experiences.

Key Responsibilities

As a Regional Sales Manager, Luxury, you will lead efforts to elevate our presence within the luxury travel space. Your key responsibilities will include:

• Strategic Account Management: Own and grow a portfolio of high-value agency accounts. Develop tailored partnership strategies to meet and exceed revenue targets.

• Luxury Supplier Optimization: Promote and elevate our portfolio of preferred luxury travel suppliers, influencing advisors’ product choices to drive profitability.

• Territory Planning: Prioritize relationship-building and engagement efforts within your assigned territory to maximize impact and brand presence.

• Consultative Sales: Act as a trusted advisor to agency partners, aligning their client needs with our exclusive product offerings and premium experiences.

• Goal Alignment: Collaborate closely with partners to define shared revenue objectives and implement action plans to achieve them.

• Strategic Planning: Build long-term growth through detailed account planning for top-tier luxury partners.

• Business Development: Identify and cultivate new agency relationships with high growth potential in the luxury segment.

• Advisor Support: Deliver white-glove support through regular communication, bespoke training sessions, and tailored marketing resources.

• Industry Representation: Serve as a sophisticated brand ambassador at luxury travel events, trade shows, and webinars—both in person and virtually.

• FAM Trip Leadership: Design and host elevated familiarization (FAM) trips to premier domestic and international destinations.

• Responsive Service: Provide timely, solution-focused support to agency partners, ensuring satisfaction and long-term loyalty.

• Sales Performance: Continuously meet or exceed sales targets through a strategic, insight-driven approach.

• Data-Driven Insights: Leverage CRM and analytics tools to monitor performance, track engagement, and uncover new opportunities.

• Market Intelligence: Stay informed on competitor activity and emerging trends in the luxury travel market; report key findings to leadership.

• Cross-Functional Collaboration: Participate in company initiatives and special projects that support broader business objectives

​Qualifications & Experience

We are looking for an accomplished professional who brings:

• A bachelor’s degree or equivalent experience (minimum 3+ years in sales, partnership development, or a client-facing role)

• Previous experience in luxury travel, hospitality, or high-end consumer sales preferred

• Ability and willingness to travel up to 70%, including air and ground travel for events, partner meetings, and FAM trips

• Exceptional consultative sales and relationship management skills

• Strong understanding of luxury client expectations and premium service standards

• Confidence in analyzing sales data and using reporting tools to drive performance

• Excellent verbal and written communication skills, including presentation and active listening abilities

• A polished, professional presence and genuine passion for luxury travel

• Must be eligible for enrollment into the company AAA Safe Driving Program

This is a rare opportunity to contribute to a brand at the forefront of luxury travel while building influential relationships and curating unforgettable journeys.

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

Territory: ND, SD, NE, KS, OK, TX, MN, IA, MO, AR, LA, WI, IL, IN, MI, OH, KY, TN

Compensation: Regional Sales Manager, Luxury is on a base salary plus incentive program with earning potential based upon the achievement of certain corporate financial and personal business goals and objectives for EVOKE | INSPIRE; most earn between $65,000 - $90,000 annually.

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!

Pleasant Holidays is one of the largest travel wholesalers in the United States, specializing in vacation travel to the Hawaiian Islands, Caribbean, Central America, Europe, Mexico, Middle East, South Pacific (Australia, Cook Islands, Fiji, New Caledonia, New Zealand & Tahiti), Japan, the United States & Canada, and cruise vacations worldwide. Pleasant Holidays is a subsidiary of the Automobile Club of Southern California, a diversified insurance, roadside assistance, financial services and travel organization serving more than 18 million AAA members across 24 states.

Pleasant Holidays is an Equal Opportunity Employer

Our organization participates in E-Verify

Pleasant Holidays will consider for employment all qualified applicants, including those with criminal histories, in a manner consistent with the requirements of applicable federal, state and local laws