Midwest Regional Manager, Field Sales.

Midwest Regional Manager, Field Sales – Luxury Hospitality Brand

Location: Remote (Must reside within territory)

Territory: TX, OK, KS, NE, SD, ND, CO, MN, IA, MO, WI, IL, IN, MI

Employment Type: Full-Time

Compensation: Competitive Base + High-Earning Commission Structure

Are You a Driven Sales Leader Ready to Represent the Pinnacle of Luxury Travel?

PrideStaff has been exclusively retained by a premier, globally recognized luxury hospitality brand to find an extraordinary Midwest Regional Manager of Field Sales .

If you thrive on closing high-ticket business, building executive-level relationships, and turning unique luxury experiences into lucrative sales, this is your opportunity. This high-impact, hands-on business development role focuses on driving group bookings and full-yacht charters across a prime 14-state territory.

Why You’ll Love This Role

Uncapped Earning Potential: Enjoy a strong financial baseline paired with a highly attractive, lucrative commission model built to reward top performers.

Luxury Travel Perk: Receive up to 14 days of complimentary luxury travel benefits annually for you and a companion after 6 months of employment.

Autonomy & Impact: Manage your territory as your own business while representing a world-class luxury brand.

Comprehensive Benefits Package:

Medical, Dental, and Vision Insurance

Short-Term and Long-Term Disability Coverage

Life Insurance & Long-Term Healthcare Coverage

SIMPLE IRA with Company Match

Generous Paid Vacation, Sick Leave, Personal Days, and Paid Holidays

What You’ll Do

Drive Revenue: Develop and execute a targeted territory sales plan exclusively focused on closing high-value group and private luxury charter bookings.

Prospect & Pipeline: Proactively identify and engage travel advisors, corporate decision-makers, incentive planners, affinity groups, and high-net-worth event planners.

End-to-End Sales Management: Manage the full sales lifecycle from initial outreach and qualification to proposal development, high-stakes negotiation, and closing.

Field Engagement: Represent the brand at trade shows, top-tier industry conferences, and high-impact networking events.

Modern Sales Execution: Leverage CRM platforms alongside cutting-edge AI and automation tools to streamline research, personalize client outreach, and optimize pipeline management.

What We’re Looking For

Proven Luxury/Group Sales Success: Demonstrated track record selling group travel, private charters, corporate incentive travel, or ultra-luxury hospitality experiences.

Established Industry Network: Existing relationships with top travel advisors, event planners, and corporate buyers are a major plus.

Closing Mastery: Strong ability to understand complex client needs, craft compelling proposals, and close multi-figure deals.

Tech & AI Savvy: Comfortable utilizing modern CRM systems, sales automation, and AI productivity tools to work efficiently.

Road Warrior Mindset: Willingness and ability to travel frequently throughout the assigned territory, including occasional evening and weekend industry events.

Apply Today

Ready to elevate your sales career with a global leader in luxury hospitality? Submit your resume today for immediate and confidential consideration by the PrideStaff team.