His career spans several decades, during which he has significantly influenced the intersection of hospitality and technology. Siegel's journey into the hospitality sector began in the mid-1970s. Starting as a bellhop and front desk clerk, this hands-on experience provided him with a solid foundation in hotel operations and guest services.

In the early 1980s, Rich's interest shifted towards the technological aspects of the hospitality industry. While working as a front office manager in New York City, he became fascinated with property management systems (PMS) and their potential to streamline hotel operations. This interest let him to work for the three largest property management systems at the time starting as an installer with Hotel Information Systems (HIS) which led to a sales position, followed by sales positions at Computerized Lodging Systems (CLS) and then Lodgistix.

After selling property management systems for hotels for a decade, he recognized a gap in the market for a publication dedicated solely to hospitality technology, so in 1992 Rich founded Hospitality & Automation, a precursor to Hospitality Upgrade. Printed on bright yellow paper, the newsletter aimed to educate and inform both technology enthusiasts and industry professionals about the latest trends, innovations, and best practices in hospitality technology. The publication grew to reach over 30,000 readers across more than 80 countries, solidifying its position as a leading resource in the industry.

In addition to his work with Hospitality Upgrade, Rich also founded two highly regarded industry events: The CIO Summit and The Executive Vendor Summit. These gatherings are designed to foster collaboration and dialogue among top executives in hospitality technology. The CIO Summit brings together chief information officers from leading hotel companies to discuss pressing issues, share insights, and explore innovative solutions. Similarly, The Executive Vendor Summit offers a platform for technology vendors to engage with industry decision-makers, forging meaningful partnerships and driving business growth. Both events have become vital to the hospitality technology ecosystem, reflecting Siegel’s commitment to advancing industry knowledge and promoting relationships that drive success.

Rich's dedication to advancing hospitality technology has been widely recognized. In 2003, he was inducted into the HFTP International Hospitality Technology Hall of Fame, an honor bestowed upon individuals who have made significant and lasting contributions to hospitality technology. His work with Hospitality Upgrade has been instrumental in fostering communication between vendors and customers, thereby enhancing productivity and efficiency within the industry.

Beyond publishing, Rich actively engages with industry leaders and professionals. He also contributes to discussions on emerging technologies and their implications for the hospitality industry. He is the author of the popular Siegel Sez newsletter which has been published since 2001. Through his work with Hospitality Upgrade, he has played a crucial role in educating and connecting professionals within the industry.

RICHARD’S INDUSTRY PREDICTIONS:

THE CIO’S JOB ISN’T WHAT IT USED TO BE – TECH LEADERS IN HOSPITALITY AREN’T JUST KEEPING THE LIGHTS ON ANYMORE—THEY'RE SHAPING THE GUEST EXPERIENCE, DRIVING REVENUE, AND MAKING BUSINESS-CRITICAL DECISIONS. IF YOU’RE JUST “THE IT GUY,” YOU WON’T BE FOR LONG.

AI IS TAKING OVER (AND THAT’S A GOOD THING!) – HOTELS ARE DOUBLING DOWN ON AI TO MAKE GUEST EXPERIENCES MORE PERSONAL—SMARTER RECOMMENDATIONS, QUICKER SERVICE, AND LESS OF THAT COOKIE-CUTTER FEEL. IF YOU’RE NOT USING AI YET, YOU’RE ALREADY BEHIND THE CURVE.

HOSPITALITY IS STILL A PEOPLE BUSINESS—TECH JUST HELPS – NO MATTER HOW ADVANCED THE TECH GETS, GREAT HOSPITALITY STILL COMES DOWN TO PEOPLE. THE BEST HOTELS WILL BE THE ONES THAT USE TECHNOLOGY TO ENHANCE SERVICE, NOT REPLACE IT.