Chief Difference Maker sees opportunity to change events work for the greater good
Society for Incentive Travel Excellence (SITE) CEO Annette Gregg sees events as big business that is also personal. This energetic, Southern California-based leader has worked in all aspects of events, including corporate, association and non-profit, convention center, DMOs, a DMC, agencies and as a program advisor and instructor at San Diego State University overseeing Meeting & Event Certificate content. She even launched what turned out to be a personally cathartic women’s event. She was an executive with Meeting Professionals International (MPI) before taking her current role at the end of 2022. Through it all, she has focused on the gifts hospitality bestows on all it touches.
“I’ve seen an emphasis on business impact and on incorporating neuroscience and emotion into meeting design,” she said in the aftermath of a 2026 SITE Global Conference themed “Wonder, Awe & Curiosity” staged in Abu Dhabi, the capital of the United Arab Emirates. A heightened understanding of human behavior and international travel trends has enhanced the stature of event planners and the impact of their work. And Gregg is there for all of it.
The Gratitude Lens
In Gregg’s previous consulting role, she was known as Chief Difference Maker. She still wakes up every morning focused on giving back as a way of thanking those who helped her get where she is today. “I am grateful for this career and the opportunities it’s allowed. I’ve had wonderful mentors and bosses and been fortunate to travel the world,” she said.
One of the ways she has supported the events community was by working with an advisory council to launch Rise Up, a multi-day annual women’s conference that brought diverse audiences together for healing. It ran from 2016 to 2018. Building content for women in their 40s dealing with insecurities related to empty nest syndrome, reentering the workforce and career stagnation ended up having a personal healing effect. She had recently been laid off and was grappling with fear and self-doubt. “Ironically, I had been teaching for years about overcoming self-limiting beliefs and creating a powerful self-brand and then I had to confront it myself,” she said. “It’s one of the projects I’m most proud of in my professional journey.”
The process was also eye-opening. “I began working with companies on DEIB initiatives and training on unconscious bias. What I learned was insight into the inherent inequities in employment, pay and advancement opportunities, and how we need to be intentional to overcome those gaps,” Gregg said.
“We have a huge opportunity. Over half the workforce is under 40 years old, and over half of our industry turned over since the pandemic. Those of us who are more seasoned are the brand ambassadors for this industry—either positive or negative,” she said pointedly.
“Entering the workforce and looking for jobs can be dehumanizing. Our industry has so much variety in roles that it can be overwhelming. We can provide a warm welcome and a path for new entrants,” she challenged with a sense of urgency. “As a large portion of our industry will be retiring in the next decade, we have to be intentional about recruiting the next generation of event professionals.”
“Ironically, I had been teaching for years about overcoming self-limiting beliefs and creating a powerful self-brand and then I had to confront it myself.”
– Annette Gregg
Gregg formally and informally mentors people every year—young professionals looking for work, people negotiating salaries or their next move, or anyone just needing a morale boost. “I believe it’s our job to give back,” she said.
Gregg’s son, Evan, heard her message loud and clear. He now performs business development for the event management company GoGather. He told his mother that he loves seeing people’s joy when they come together to share experiences. “I know he picked the right industry!” she said.
Greater Good
When asked about her legacy, Gregg looked forward more than she looked back. “The longer I’m in our industry, the more I believe in the power of being together,” she said. “With global depression and isolationism rising, bringing people together to break down walls and build understanding is more critical than ever.”
Gregg returned to her gratitude practice to sum up her journey. “I know this is my God-given calling, and I’m grateful to have found an industry that has this impact. I hope to continue to grow our industry, and that event professionals see this greater good in all their hard work.”
Measurement, Entrepreneurship and Intentionality—Positive Shifts
A lot has changed since Gregg’s first hospitality gig in 1995—much of it for the better.
The Triple Bottom Line: “In corporations, meetings and events are usually considered cost centers versus revenue centers,” Gregg noted. That is a problem because these programs become vulnerable to reductions when economies are down. The good news is that meeting and event professionals are now savvier about measuring and articulating how events move businesses forward. For incentive travel—a segment worth more than $300 billion annually—proof points could include a direct line to driving sales and increasing loyalty and retention.
Stepping Into Entrepreneurial Power: Another trend that gives Gregg hope: proliferation of the Event Boss. “I’ve noticed a rise of entrepreneurialism over the past decade, partially driven by younger generations. They watched economic disruptions cause layoffs and how older generations have worked themselves into an unhealthy lifestyle and they want to take matters into their own hands to control their work life,” she said.
Hospitality on Purpose: Zillennials (Gen Z and Millennial workers) are marking a change she sees as healthy. “We’ re seeing more university students intentionally choose our industry versus accidentally finding it like many of us did,” Gregg observed. She saw their rise through experiential marketing programs as an opportunity for “an exciting creative boost.”
