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.

Q: How would you describe your leadership style?


A: I don’t know how I’d describe it, but somebody described it to me as fun but direct. I think I have a very good sense of humor, and I try to enjoy my time and make the workplace really enjoyable and fun. You know, startups and growth companies, and jobs in general, people spend enough time at them that for people not to be enjoying what they do is disappointing. So I really want the company and the culture to be as enjoyable and fun as possible. That goes hand-in-hand with high levels of productivity and a need to both work really hard and to drive success for our clients. I try to be very direct and as transparent as possible so everyone knows what’s expected of them. People can be accountable to themselves and to each other, care about each other, but ultimately have a lot of fun.

Q: Your background is pretty diverse. Is there a common thread that runs through your career thus far and the positions you’ve held?

A: My career has been one in which I’ve largely focused on software and Internet companies that serve marketers and e-commerce professionals. All the software and all the solutions that companies that I’ve been involved in, almost all of them are related to customer relationship management, e-commerce, marketing automation, loyalty marketing, offers and promotions. I started my career in strategy consulting and them joined one of my clients in product management. I was a so-so product manager but a very good product marketer, so I started as a product professional, and then expanded to product marketing, and then expanded to sales and marketing and became (chief operating officer), had a broader set of responsibilities, engineering services, client services, and then obviously had the recent opportunity to expand it more completely and become president and CEO of CashStar.

Q: What are your primary goals as the head of CashStar?

A: I think most importantly, we want to drive real value for our clients. I think that if you concentrate on delivering value for your clients, a lot of things then come along for the ride. You’re going to get the revenue that’s associated with it. You’re going to have a growth rate that’s meaningful. Your employees and your clients are going to have a shared sense and reality of success. And then ultimately, if you build value, if you deliver value for your clients and you deliver value for your investors, the outcome for the company, whether it’s achieving profitability or perhaps one day going public, those types of outcomes ultimately take care of themselves. You have to be very disciplined, and it isn’t quite as simple as, ‘Hey if you deliver value for your clients…’ But ultimately, if that’s where your focus is, a lot of good things are going to come along for the ride.

Q: What is the significance of the holiday shopping season for CashStar?


A: It’s a very exciting time of year. CashStar works with retailers, and in fact our business model hews very close to a retail business model in the sense that something to the tune of 35 to 50 percent of a retailer’s revenue is typically in (the fourth quarter), during holiday season. We have that same type of revenue curve, so all of this year, in many respects in terms of implementing our new products, rolling out new clients, comes to a very exciting head in November and December.

There’s a huge number of promotions that our clients run using our digital gifting platform as a really interesting promotional currency. One of the things that’s most exciting about digital gifting is that its potential is beyond just instantiating a plastic gift card in a digital environment or on a mobile phone. It really is about converting or transforming a plastic gift card into a digital promotional currency that can be used for any number of business goals: driving customer acquisition, in-store sales, new store launches, new product launches …. So there’s a range of marketing goals that our innovative retailers are using digital gifting for.

Q: What do you enjoy doing outside of work?

A: First and foremost, I enjoy spending time with my family. I have two little kids, a 7-year-old and a 4-year-old, and those are great ages. They really love and enjoy their parents, which may not last forever, so I’m really trying to sort of drink all that in while I can. As a family we like to play a lot of sports together, we like to travel together. I don’t see as many movies as I used to, with kids, and the movies that I see are things like “Monsters University,” which is perfectly enjoyable, there’s nothing wrong with that. But pretty much, outside of work, family-oriented, and my one sort of vice is (being) a crazy Boston sports fan.

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