Become a Marketplace Leader
We're recruiting visionary leaders to anchor pickleball + Dream Trips expansion in 10 key US markets. If you're the kind of person who builds culture, scales leaders, and shows up — this is for you.
America's fastest-growing sport meets the world's best lifestyle brand.
Pickleball is exploding. DreamTrips is the proven engine. The Expansion Leaders Group is putting Marketplace Leaders on the ground in cities where momentum is highest — and we want to talk to the right people first.
Is this you?
The framework we use to identify Marketplace Leaders and future Directors of the Expansion Leaders Group.
Leadership Characteristics
Can you scale people?
- Vision-casting ability — clearly articulates where we're going and why
- High emotional intelligence — reads rooms, handles conflict
- Servant leadership — elevates others, creates leaders
- Decisiveness — moves quickly, doesn't freeze under pressure
- Accountability-driven — holds standards consistently
- Adaptability — comfortable in ambiguity and fast growth
- Integrity — same person on stage and off
- Humility with confidence — secure enough to admit mistakes
- Systems thinker — creates repeatable frameworks
- Influence without authority — moves people who don't report to them
Brand Ambassador
The face of the organization
- Natural relationship builder
- Magnetic energy
- Professional presence
- Excellent communicator
- Authentic and optimistic
- Community-minded
- High follow-through
- Strong storyteller
- Highly coachable
Visionary
Sees opportunity early
- Sees trends before competitors
- Thinks in 3–5 year windows
- Questions assumptions, challenges status quo
- Innovative, big-picture, strategic mindset
- Connects dots rapidly
- Action-oriented and curious by nature
Director-Level
Scale at 25–50 leaders
- Develop leaders
- Build systems
- Create culture
- Monitor KPIs
- Recruit and retain talent
- Create succession plans
- Align everyone around the vision
- Run every event
- Solve every issue
- Be the best player
- Micromanage
Competency Matrix
How we weigh Director-level performance.
10 cities. One leader each.
Click your city to learn more and apply.
Florida
Fort Lauderdale
Coastal energy meets year-round play.
St. Augustine
Historic charm, modern movement.
Orlando
Central Florida's growth engine.
Naples
Premium players, premium experiences.
Emerald Coast
Sugar-white sand, year-round courts.
National
Apply to lead your city.
Tell us a little about you. We review every application personally.
Ready to live the Dream?
The pickleball boom + the travel boom = your moment. Don't watch this one go by.