In Good Company: Pam Kressley & Lori Cassidy on Big Leaps, Shared Vision, and the Power of Rewarding Well
- amanda7443
- 4 days ago
- 5 min read
In Good Company is a series by AUTHENTIC Meetings & Incentives® that highlights the people behind the brands shaping today’s incentive travel landscape.
This week, we sat down with Pam Kressley and Lori Cassidy at Gift-a-Trip...
Pam, you spent nearly 30 years helping others build their brands and their dreams. What made you decide it was finally time to bet on your own?
I’ve always been an entrepreneur at heart. Even when I was working for other companies – I approached my role and treated my sales region as if it was my own personal small business. I felt that regardless of who you work for - whether it’s someone else or yourself - you need to carry yourself every day knowing that your decisions, your responsiveness, and your work ethic reflects not only who you are as your own personal brand, as also effects your bottom line. So deciding to finally go out on my own was easy. It was just a matter of finding the right solution, and the right business model, along with the right business partner, at the right time.
Lori, you’ve been alongside Pam for most of that journey. What do you think she saw in you that made her want to build something from the ground up together?
I believe that when someone chooses to build a company from the ground up with another person, it usually means they see qualities in that person that align with their own values, goals and ambitions. Pam and I not only trust one another inherently, but we also have a shared vision and passion for this business. Our complementary strengths and commitment to delivering excellence on all levels are just a few reasons as to what makes our partnership not just work, but thrive.
Pam, this business is rooted in joy, but also in a clear gap in the market. What was missing from the travel space that you felt compelled to create?
Lori and I realized that outside of the turnkey certificate that we offered with Royal Caribbean (where we both worked for over a decade), our industry struggled to provide simple solutions when it came to individual travel rewards. They’re inherently clunky – typically requiring a lot of time and effort not only to source, but to deliver and execute. And without any guardrails built in, it can quickly get very granular, and take up a lot of a planner or administrator’s time. Our goal was to simplify the process, by offering a wide variety of trip options at a wide variety of price points, with easy, turnkey direct-to-supplier fulfillment. This not only saves time, but money, and a lot of resources along the way. We knew we could do it better.
Lori, what’s a moment since launching Gift-A-Trip that made you pause and think: “This is working. We’re doing something that matters."
Out of the gate, Pam and I knew we were on to something, noting the void that existed in the marketplace for turnkey individual travel certificates from the top resort, hotel and cruise brands. Knowing that we have a created a solution for corporate buyers to seamlessly reward and recognize with the gift of travel is extremely satisfying, and we actually have to pinch ourselves from time to time to appreciate all that we have accomplished in just a few short years. I can’t tell you how many times, clients have asked us “Where have you been, as your solution is exactly what we need and have been looking for!” – THIS validates the impact and necessity of what we have created.
Pam, when someone receives a certificate, they’re not just being given a trip, they’re being seen, celebrated, remembered. Why do you think that kind of giving feels different?
A trip isn’t just a thing - it’s an experience. Plus, trips are often seen as a luxury, something people might not give themselves. So when someone is rewarded with a trip, it signals that their contributions were exceptional. It’s not just a thanks, it’s an honor.
Lori, what part of this work still takes your breath away?
When I take a step back and reflect on the last few years, I truly have to pinch myself and say ‘WOW’—look at what we’ve created. From the early days when it was just an idea to now seeing how far we’ve come, the journey has been nothing short of incredible. It’s not just about the business, it’s about the lives we’ve impacted, the partnerships we've built, and the people who believe in what we're doing. We don’t always take the time to celebrate our wins, because we’re always focused on growth. But those moments of reflection remind me that what we’ve built is bigger than I ever imagined, and it’s humbling to see the ripple effects of our work.”
Pam, what have you had to unlearn in order to build this the way you wanted to?
As the saying goes, “perfection is the enemy of progress.” I’ve often believed that if it’s not perfect, it’s not ready. But when starting a business, perfection is a moving target and it can stall momentum. Building something meaningful often means unlearning that fear of imperfection, and instead trusting the process, and the learning that comes with doing.
I’ve also had to unlearn the need for external validation. In our business, we celebrate our wins and learn from our losses in real time, not whether we’ve ‘won’ or ‘lost’ against an externally set quarterly or annual quota. So that’s been quite an adjustment.
Lori, what do you hope people remember, not just about Gift-A-Trip, but about you, and the mark you left on this industry?
I hope to be remembered as someone who always led with my heart, not just my head. I wasn’t afraid to take risks, to embrace bold ideas, and to encourage others to think outside the box because I believed that innovation doesn’t come from playing it safe, it comes from pushing limits and daring to dream bigger. Ultimately, I want to be remembered for the positive change I’ve contributed to people’s lives and for the relationships I’ve helped build and strengthen. I also hope my work has had a meaningful impact within the travel industry, one that has helped push it forward and made a difference in the way we create and experience travel.
Looking to Reward Differently?
Gift-A-Trip offers turnkey travel certificates that trade clutter for connection. Discover how they’re redefining recognition, one trip at a time.
Know someone who should be featured next?
Nominate a colleague whose story deserves the spotlight. We’re always looking for leaders, legends, and the voices shaping the future of incentives.