Empower Your People: Staypineapple's Dina Belon-Sayre on Personality-Driven Hotels and the AI Threat to Independents

This Week’s Guest:

Dina Belon-Sayre - President, Staypineapple Hotels LinkedIn: https://www.linkedin.com/in/dinabelon/ Explore Staypineapple Hotels: https://www.staypineapple.com/

Your Host:

Zach Busekrus - Journey LinkedIn: https://www.linkedin.com/in/zachbusekrus/ Instagram: https://www.instagram.com/behindthestays/

Dina Belon-Sayre, President of Staypineapple Hotels, opens with a story from a Portland snowstorm when she waited tables herself, fed a stranded hotel and received a thank-you check from a guest. Her point: any Staypineapple employee is empowered to make the same call. She traces her unusual path from theater, psychology and criminal justice studies through hotel design, construction and a decade in sustainability consulting, to spotting a five-story painted pineapple from her Seattle office window and joining the company ten years ago. She rose from director of real estate to president. Dina explains the upside of a playful, edgy brand (the "Naked Experience," no navy blazers or scripts) and the occasional offended guest, and why it's fine not to be for everyone. She describes hiring for emotional intelligence, critical thinking and a willingness to be authentic. On growth, she notes owners are risk-averse, Staypineapple hasn't franchised without management because service is the brand's through-line, and the company may package tools for other independents. Her soapbox: AI and LLM booking could run over independents within 18 months, and collections may need to become their AI intermediary at a fair cost.