Leadership Pathways, Curiosity, and Continuous Growth in Hospitality Technology

Jacob Messina describes discovering hospitality through video games that sparked his interest in managing complex operations and understanding human behavior. He began working in restaurants at 16 before moving into hotels, where front desk roles launched his hospitality career. Jacob reflects on becoming interim CEO and learning to scale his leadership from managing 12 people to over 150 across 18 countries. He focused on understanding individuals as humans, not just employees, and brought a customer-led mindset from his prior role as a client.

Curiosity has been a driving force throughout his progression. He explains rising early in his career by taking on responsibilities without being asked and continually asking “why” to understand processes. He uses two interview questions, what candidates are curious about and a failure they learned from, to reveal how people think. Jacob discusses recognizing leadership in himself only after realizing he had been leading through influence, collaboration, and cross-organizational work.

Notable Quotes/Highlights

• “Asking questions is probably the most powerful thing that you can do.”
• “I honestly never really saw myself as a leader in the early stages of my career.”
• “I don't think you can lead from an ivory tower.”
• “Everything takes longer than you think it's going to.”
• “It's okay to fail… as long as you learn from it.”

Closing Reflection

Jacob’s reflections emphasize curiosity, intentional learning, and leading through authentic relationships. He underscores the value of spending time with customers, understanding how people use technology, and avoiding assumptions. His experiences show how leadership grows through trust, communication, and embracing complex challenges. He reminds listeners that setbacks create learning moments when viewed thoughtfully. Throughout his journey, he demonstrates that questioning, listening, and investing in others drive meaningful progress in a fast-changing industry.