Role: Director of Sales - Offshore Rooftop at Navy Pier, Chicago, IL Revenue Leader | Experience Architect | High-Performance CloserOffshore Rooftop is one of Chicago's most iconic high-volume hospitality destinations-where skyline views, curated experiences, group business, and ticketed programming come together to create a powerful, multi-stream revenue engine.
We are seeking a
dynamic Director of Sales who operates at the intersection of hospitality, entertainment, and commercial strategy. This is a leadership role for someone who doesn't just manage demand-they create it.
Who You AreYou are a hospitality revenue leader who blends commercial discipline with creative thinking.
You:- Build demand and convert opportunity at speed
- Operate with urgency, precision, and consistency
- Think in pipeline velocity, pacing, and revenue optimization daily
- Turn experiences into scalable revenue streams
- Thrive in both corporate group sales and high-energy social/event environments
- Lead teams with accountability, energy, and performance standards
- Are equally comfortable closing high-value corporate accounts or high-volume experiential business
What You OwnYou are accountable for the full commercial lifecycle of group, event, and experiential revenue:
- Full-cycle sales: lead generation, qualification, conversion, and retention
- Corporate, social, association, and partner channel development
- Pipeline management, forecasting, and revenue pacing discipline
- Ticketed experiences and programming revenue in partnership with operations and marketing
- Proposal development, negotiation, contracting, and deposit capture
- Seamless execution through accurate Banquet Event Orders (BEOs)
- Post-event follow-up, repeat business, and referral growth
- Leadership, coaching, and performance management of the sales team
- Schedule flexibility, including evenings and weekends, aligned with business and event demand
What Success Looks LikeSuccess in this role is defined by measurable commercial impact:
- Consistent achievement of group and experiential revenue targets
- Strong pipeline visibility with predictable pacing and conversion rates
- Growth in ticketed and non-traditional revenue streams
- Expansion of repeat business and strategic account relationships
- A high-performing, accountable, and motivated sales team
- Strong alignment between sales strategy and operational execution
Why OffshoreThis is not a traditional sales role.
At Offshore, you are not selling space-you are
building demand, shaping experiences, and driving revenue across multiple streams of business.This is a rare opportunity to:
- Build and scale a experiential revenue model
- Influence how one of Chicago's most dynamic rooftops monetizes its platform
- Operate at the intersection of hospitality, entertainment, and commerce
- Directly impact top-line revenue in real time
