Sales Support and Events Supervisor

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 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 17 million AAA Members across 21 states.

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