A Word With the Boss: CashStar CEO Wraps Gifting Challenges With Fun

Ben Kaplan is about to experience his first Black Friday as president and CEO of Portland-based digital gifting firm CashStar Inc. Kaplan joined the company in August as chief operating officer and took over as chief executive in October. The holiday shopping season is crucial for CashStar, whose clients include retailers such as Starbucks, Dunkin’ Donuts, Best Buy, The Home Depot, Banana Republic, Old Navy and Pizza Hut. The clients sell electronic gift cards online through websites that CashStar runs. Consumers can custom-design electronic cards with videos, photographs and personalized messages. The company earns as much as half its annual revenue in November and December.

Q: Tell us a little bit about yourself.
A: I grew up in the Boston area … a pretty nondescript childhood, went to Harvard College, and then when I graduated school, I moved out to San Francisco, where I worked for a range of technology companies and startups. I was there for over a decade, most of the time in Silicon Valley, although I lived in San Francisco. Eventually I moved my then-girlfriend, now-wife, out to California. She did not take to California living as I had. Collective happiness was higher returning to Boston, where she was from as well. So we moved back to the Boston area around seven years ago.

Q: What brought you to CashStar?
A: When I moved back East, I joined a company called Cartera Commerce as (chief operating officer). Cartera was, and still is, a very successful company at the intersection of payments and marketing, and offers to consumers. CashStar was looking for a new CEO, and I knew a couple of the investors, who reached out to me in the spring. There were a lot of similarities between CashStar and Cartera, but in fact many things that were just even more exciting about CashStar. The quality of the team, the people, the great products that the company had developed. I think most significantly, the incredible traction that the company had with retailers made it an opportunity that was really exciting and for sure worth exploring.