Pleasant Holidays’ Former CEO Jack E. Richards Predicts “Bright Future” for Travel Advisors

Industry veteran Jack E. Richards is stepping down as Pleasant Holidays’ CEO at the end of this month, ending an impressive 46-year career on a high note. 

Speaking with TMR in an exclusive interview, Richards said he’s looking forward to shifting gears. After nearly half a century of working in the industry, he now can enjoy travel from the other side.

“Travel will still be my primary interest going forward. I’ll be looking at the industry from the outside, so it’ll give me a different perspective,” Richards told TMR. “Believe it or not, I had the wanderlust—the bug—early on.”

Jack E. Richards: From Classified Ad to CEO

As a young man, Richards knew he wanted to see the world. He set out to become a diplomat, obtaining an undergraduate degree in political science and a graduate degree in international policy and relations. But when he saw a job posting for an airline subsidiary, he decided to walk a different path.

“I got the job from a classified ad,” Richards told TMR with a smile. “It said, how would you like to travel the world? And I said yes.”

Richards was hired by the luxury brand for the role, which involved taking groups all over the world—more than enough travel to whet the young professional’s appetite. 

“They threw me into the fray,” he said.

After two years, Richards was promoted into management and then worked his way up at American Trans Air. His responsibilities grew to include negotiating with suppliers and putting vacation packages together. He stayed with the company for 14 years, eventually becoming vice president before leaving to join America West Airlines, leading its vacations division; he was named president and CEO in 2001. 

In 2007, Richards made another major move: taking over leadership at Pleasant Holidays. His tenure at the tour operator has been marked by resilience and innovation. Surviving both the 2008 recession and the COVID-19 pandemic, Richards’ leadership has allowed the company to thrive. Today, Pleasant Holidays now includes expedition and adventure packages, and has expanded from focusing on Hawaii to offering vacations in 84 countries worldwide.

“I’ve accomplished everything I set out to do in 2007,” Richards said. “I set out to expand and grow the portfolio of this company, and that’s what I’m most proud of today. … I’m proud of all the accomplishments that we as a team had together over 17 years.”

Why Pleasant Holidays Needs Travel Advisors

One such accomplishment is the number of awards Pleasant Holidays has received under his leadership, including an impressive 17-consecutive WAVE awards for Best Tour Operator, Hawaii. 

“I’m also proud of the record number of awards for service quality excellence that we’ve received,” Richards told TMR. “That just doesn’t happen because you’re lucky—that happens because people in the industry vote for you, and that’s very important to us.”

In general, Richards is quick to acknowledge how important the trade is to Pleasant Holidays. Over 95% of the company’s business is driven by travel advisors, and over 50,000 home-based and independent travel advisors are listed in Pleasant Holidays’ system—some of which are million-dollar producers.

“Our key differentiator is customer service. It’s not price—we are not about the lowest price. We are about providing exceptional service during, prior to, and after travel. That’s what keeps travel advisors with us,” Richards explained. 

“When you travel the world, a lot of things can go wrong at any time, and [travelers] need somebody to talk to 24/7. We provide that service,” he continued. 

Richards said the company has been able to attract a record number of travel advisors because it diversified its destinations.

“Although Hawaii is important, we now have a lot of other destinations to rely on to generate sales,” he said.

“Anyone in this business has a bright future going forward”

Richards believes that the travel advisor industry will continue to go from strength to strength over the next decade.

“I’ve listened to the demise of the travel advisor [claims] since 1999. ‘Oh, they’re going away, no one needs them anymore…’ That’s not true. In fact, during the pandemic, they were needed more than ever before. Now people realize that if you’re booking luxury travel, you need someone to help you along the way,” Richards explained.

The industry veteran argues that the biggest challenge the travel industry needs to overcome is simply attracting a younger generation of workers. 

“Once you do that, things will even get better and better—and better,” said Richards, adding “anyone in this business has a bright future going forward.” 

Richards’ main piece of advice for newcomers? Take as many opportunities as possible to travel. 

“The biggest thing is, you will be successful if you can speak about the destinations you offer. So you have to travel there and experience yourself. The more you travel, the better you will become and the easier it will be to sell it.”