Vacation & Travel Group is hiring a Sales Leader to own field strategy and performance across a national event circuit in Chicago, IL.

Own event sales results end to end with full P&L accountability for package-sale performance.
Lead the team to hit or exceed package-sale targets by managing day-to-day execution at activations.
Adjust scripts, pitch approach, and closing techniques in real time based on what’s working on the event floor.
Oversee booth logistics and team positioning to maximize prospect engagement at premium locations.
Coordinate with executive leadership to deliver reporting on KPIs, lead quality, and event ROI.

3–5+ years in Sales Management or Assistant Manager work specifically in OPC, timeshare, or vacation package sales.
Proven ability to step into any booth and model effective selling for reps who are struggling.
Experience managing 1099 sales teams, including the unique challenges of mobile and event-based operations.
A strong “rolodex” of proven reps or a track record for identifying raw talent in a crowd.
Willingness and ability to travel 75–90% of the time to lead teams on-site at major national activations.

Flexible schedule.
$120,000–$180,000+ OTE: competitive base salary/draw plus overrides tied to total team production.
Uncapped growth as the event calendar expands and the team scales.
Weekly performance bonuses based on team volume and package-to-tour conversion rates.
Autonomy: premium venues and logistics are provided, with leadership driving execution and strategy.

Operates as a People Architect focused on coaching and performance.
Understands OPC sales intensity and can maintain high team energy across multi-day events.
Prefer being on the floor at major activations (for example, boat shows or music festivals) over office politics.

Provide a brief summary of your leadership history, including how many reps you’ve managed simultaneously.
Provide a brief summary of your proudest turnaround story, including how you made a low-performing event/team profitable.
Confirm your ability to travel and work a national event schedule.

Work Location: On the road. Location: Chicago, IL (onsite). Salary: USD 120,000–180,000 per year. Minimum Experience: 3 years.

Sales Director (OPC/Events)

Job Description