Sales Support and Events Supervisor

At Pleasant Holidays, we empower people to be their best. As the Supervisor of Sales Support & Events, you will lead the planning and execution of corporate events while overseeing a high-performing sales support team. This hybrid role combines strategic event leadership with sales operations oversight, designed to elevate our relationships with top-performing travel advisors, industry partners, and internal stakeholders.

You will manage a team of three Sales Support Coordinators, providing daily direction, mentorship, and accountability to ensure service excellence, streamlined operations, and alignment with departmental goals.

This position requires a highly organized, proactive, and relationship-driven leader who thrives in a fast-paced environment and can balance big-picture strategy with meticulous execution.

Key Responsibilities

Team Leadership & Sales Support Management (40%)

• Manage and mentor a team of three Sales Support Coordinators, ensuring consistent execution of support tasks, training initiatives, and special projects.

• Provide daily oversight, prioritize workload, and implement process improvements to optimize team performance and service delivery.

• Serve as the escalation point for complex advisor or internal partner issues; coach team on resolution and communication best practices.

• Monitor performance metrics, conduct regular check-ins, and provide feedback to promote professional growth and accountability.

• Collaborate with Business Development Managers (BDMs) and the Vice President to align team resources with business goals and regional needs.

• Oversee distribution of sales collateral, campaign support, and training material preparation for BDMs and advisor partners.

Event Planning & Execution (40%)

• Lead the end-to-end planning of major events such as FAM trips, “Top Performer” celebrations, trade shows, local market events, and some virtual events.

• Build and manage event registration sites, attendee communications, reporting, and logistics using relevant event platforms.

• Oversee event timelines, budget tracking, venue sourcing and contracting, and coordination with suppliers and internal departments.

• Manage all event deliverables: room layouts, A/V, signage, gifting, transportation, nametags, presentations, and post-event surveys.

• Serve as the main point of contact for internal stakeholders and supplier partners before and during events.

Sales Operations & Relationship Support (20%)

• Manage all facets of agency registration utilizing our proprietary reservation platform

• Support strategic growth initiatives by evaluating monthly and quarterly sales reports to identify trends and opportunities.

• Manage key account servicing alongside BDMs, ensuring high-touch engagement with top-performing travel advisors.

• Resolve customer service or commission-related issues that surface through the sales team, partnering with Customer Service and Finance as needed.

• Coordinate and analyze performance of sales promotions, incentive programs, and marketing campaigns.

Qualifications

• Bachelor’s Degree or equivalent experience in Business, Marketing, Hospitality, or related field.

• 3–5 years of experience in event planning, sales operations, or account management; team leadership experience strongly preferred.

• Experience managing or mentoring team members, with demonstrated success in coaching, delegation, and performance tracking.

• Proficient in event management systems (Cvent preferred), Microsoft Office Suite, and CRM platforms (e.g., Salesforce).

• Strong written and verbal communication skills, with excellent attention to detail and time management.

• Comfortable handling multiple projects with competing priorities in a deadline-driven environment.

• Ability to travel (approximately 5-10 trips per year) to support key events and team initiatives.

• Travel industry or agency support experience is a plus.

Core Competencies

• Team Leadership & Development

• Strategic Execution & Project Management

• Relationship Management

• Customer-Centric Problem Solving

• Operational Efficiency

• Ownership & Accountability

• Passion for Travel and Events

Join our team and help create unforgettable brand experiences while empowering a top-tier sales support operation.

Compensation range for the position will be $55,000.00 - $70,000.00 annual.

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 an Equal Opportunity Employer

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