Live from the Marketing Vanguard stage at Brandweek 2026, Jenny Rooney sits down with Jason Pirock, former vice president of global brand marketing at Outrigger Resorts and Hotels, to discuss why differentiation may be one of marketing’s most underhyped priorities right now.
Jason challenges the industry’s fixation on ROAS and reveals why CXO titles don’t matter as much as you’d think.
He also discusses why landing a creator with a huge following can mean very little if the partnership wasn’t designed the right way.
Finally, Jason touches on why hospitality traditionally lags behind other industries when it comes to technology, and why it’s catching up now.
What you’ll learn:
- Why hospitality’s adoption of AI is accelerating after years of lagging behind other industries
- Why consumers are gravitating back toward real-world experiences and human interaction
- Why authentic creator fit matters more than reach or follower count
- Why senior marketing titles matter less than alignment with leadership
- Why ROAS should be treated as a directional indicator rather than the full definition of success
- How a builder mindset can shape a marketing leader’s career
- Why differentiation becomes even more important as AI makes generic execution easier
This episode is part of a special vidcast series that was recorded live during Brandweek 2026 and presented in partnership with Tatari.
About our guest:
Jason Pirock is the former VP of global brand marketing at Outrigger Resorts and Hotels, with nearly 20 years of experience across retail, commercial real estate, and hospitality. His career has spanned work across Hyatt, Aparium Hotel Group, Springboard, and Outrigger.
Across those roles, Jason has consistently gravitated toward building and rebuilding, from rethinking an early business at Target to putting content creators into local markets before “creator” became standard marketing language. His perspective combines brand strategy, experiential marketing and a strong belief that differentiation matters even more as technology makes execution easier.
Episode Highlights:
[04:03] Hospitality’s AI Catch-Up Is Happening Fast — Jason says hospitality has traditionally been well behind industries like retail when it comes to technology adoption. That gap is narrowing quickly. Over the past year or two, he has seen a wave of new technology companies and faster AI adoption across the sector. Much of it remains behind the scenes for now, but Jason expects more guest-facing applications to emerge, raising the stakes for brands deciding where technology genuinely improves the experience.
