Meet the Woman CEO Standing Tall in Philly’s Male-Heavy Tech Industry

Lucinda Duncalfe, CEO of Monetate. (Photo by Jared Castaldi)

Lucinda Duncalfe can’t help but stand out from the crowd. It’s not because she’s a former University of Pennsylvania basketball player who stands six-foot-one. Nor is it because she trains in Shotokan karate. It’s because she’s a woman who’s been incredibly successful in technology — an industry that’s traditionally been dominated by men.

Duncalfe’s career sounds like a fairy tale out of Silicon Valley, but it all happened right here in the Philly area. In the mid-1990s, she took a big risk (and a serious pay cut) to leave investment company SEI to join a start-up called Infonautics. After that went public, she took another pay cut to land her first CEO gig, at Destiny Software. In 2004, she founded an anti-spam company called TurnTide that sold six months later for $28 million. She went on to start Cuts.com, lead ClickEquations for five years before it sold in 2011, and launch Real Food Works, a delivery service. In all, she’s been a CEO five times.

Since August 2014, she’s served as CEO of Monetate, a Conshohocken-based company that counts Macy’s, QVC, DirecTV, True Religion and other big-time brands as clients. Monetate helps companies deliver personalized communications to consumers after analyzing their behavior across the Web, email and mobile apps. Here’s an easy example: After partnering with Monetate, Famous Footwear now optimizes its website during the winter months to show boots for people in cold states like Pennsylvania and boat shoes for customers in warmer climates like Florida.

Although Monetate was founded in 2008, it’s a company at a crossroads: Should it go public? Position itself to sell? Try to become the industry leader across different sectors? I asked Duncalfe, age 52, these questions and more while visiting the company’s headquarters, where a caterer was serving tacos to hipster-looking millennials who lounged on sofas while working on their laptops. We spoke at length about Monetate’s future, why there aren’t more women in tech, and what Philly needs to do to take its tech ecosystem to the next level.

It’s no secret that women represent a small segment of tech workers in Philly and around the country. How do we get more women into tech careers? I think role models are really important. The reality is that in a lot of technical organizations, it’s a little uncomfortable to be female. I think we have to expand the definition of what it means to be a technical person so it’s more encompassing and less unwelcoming to women. I am almost always the only woman in any board meeting or executive meeting. It takes a certain resiliency to always be the only one.

Does being the only woman ever give you an advantage? I think it totally helps. If you present to a venture capitalist and they’ve had eight entrepreneurs in that day, who are they going to remember? They’re going to remember the six-foot-tall blonde. I’m a big believer in diversity in every sense of the word, and if we don’t have women in technology, we’re not getting the best solutions, because there’s not a diverse enough group coming up with the solutions. Products are used, if not predominantly by women, by a huge plurality of women. If women don’t help to make them, the products aren’t going to be as well targeted. It doesn’t make sense to me.

How have you attempted to attract women to Monetate? We always had a really strong female presence at Monetate. I hesitate to take credit for it. I think they’re attracted to a company with a female CEO. They’re making the correct presumption that we’ll be friendlier to women.

What do the next couple of years at Monetate look like? Our mission is all about improving experiences between the brand and the consumer. We’re already leaders in the U.S. and Europe for personalization in retail. More Internet Retailer 500 clients use our platform than any other. I want to have that in all of the verticals we think are important — travel, financial services, health care. I want the company to be “IPO-able.” Which means you have to have revenues at a certain rate, a certain growth rate, and certain metrics in place. The finance guys call it “optionality.”

The retail industry is having a tough time at the moment. Can Monetate technology save retail? I believe the relationship between customer and retailer is fundamentally shifting. The power has shifted to the customer, which is driven by social media. It used to be that they’d push things at you. They’re going to advertise in the newspaper and on TV. What’s now happening is they have to put you, instead of whatever it is they’re pushing, at the heart of their business. The entire organizational structure of retailers is shifting. Instead of being focused on “I sell for TV” and “I sell for print,” they’re saying, “I focus on our high-loyalty customers” and “I focus on new customers.” That shift has to be enabled with technology that can recognize that you’re a loyal customer or a new customer — and interact with you differently.

Still, it does feel a little invasive when I search for a blender online and then see ads for blenders for the next three weeks. There’s a spectrum. We call it the creepy-to-convenient spectrum. What we’re seeing globally is, that line is moving over time. Some people feel it’s kind of handy to have these ads following them around, because one of them might be cheaper and they’ll buy that. That’s a good example because it’s right on the line. Some people find that creepy, and other people find it really convenient. Just to clarify, Monetate doesn’t do advertising. When consumers are down in the realm where we operate, they already have a relationship with the brand. You really don’t get that creepy.

Philly’s tech scene doesn’t seem primed to challenge San Francisco or New York anytime soon, but it does seem to be growing. What can we do to get to the next level? I’ve been doing this for a long time in this region, and it’s a world better than it ever has been. There’s vibrancy to it. I think the critical tipping point was students starting to stay after graduation. We have such a richness of academic institutions, and kids were all just leaving. Getting that talent to stay is a huge driver for what needs to happen going forward. I think Philly has its own identity. We have a specific kind of company that’s going to be born here and do well here. I think Monetate is an example of that. We tend to be more about what I call real businesses. We’re not going to be the ones who come up with Instagram or HipChat. But we will come up with real products that provide real value. And that fits culturally with who we are and what we do. We have some tremendous advantages over other regions: cost of living, colleges and universities. We have this can-do, hardworking culture that I think is really great.

One of the biggest things we’re missing is a connection between those who have been successful and the next generation of entrepreneurs. In some other regions, there’s a much richer culture of folks who have been successful and are now being angel investors, advisers and board members — just being active in the community of entrepreneurs, which helps them not make the same mistakes and helps them be successful.

What about Philly’s attitude toward start-ups? Does that need to change as well? There’s still a risk aversion here. I think there’s a little bit less tolerance for failure. If you go to some of the other tech hubs, they just expect that there’s going to be failure along the way, and that’s okay. In New York or the Valley, your family is going to think it’s really cool that you’re working at a start-up. Here, you’re much more likely to get, “Why didn’t you take that job offer from Comcast?”

You’ve been willing to take pay cuts a couple of times in your career. Is there a lesson there? Follow your heart. The money won’t necessarily follow, but that’s okay. I grew up with artist parents. We didn’t have a lot of money. Spend your life doing something you want to do. Why not do that if you can?

What has been the biggest turning point in your career? Becoming CEO of Destiny Software was by far the biggest turning point. I’m not generally the idea person. I partner with someone who is the idea person. It’s very hard to get your first CEO gig if it’s not your idea. Either you founded the company and became CEO or you’re inside a company and you work your way up and become CEO — and that takes decades. I am forever grateful to my friend Skip Shuda, who gave me that first shot. I look back on that and say: “What was he thinking? I didn’t know anything.”

You’re very passionate about helping people eat healthy, so you started Real Food Works, an organic food delivery service. What’s it like to work on a passion project like that? It’s different. It’s much harder to be rational. Your motivations are more complicated, and it’s not such a clear equation what winning and losing look like. It’s the only time I’ve done a physical product. You have stuff to move from one place to another. There’s a whole different world of people involved in that. At this stage of my career, at my age, it’s really fun to learn a completely different thing. Lead times are just enormous. Somebody can’t just stay up that night and code an extra meal. You’ve got to get the stuff from somewhere and package it out.

The other thing that’s just been incredible about that experience is that you get letters from people saying, “My cholesterol is down 100 points and I dropped 50 pounds,” or “I went off my insulin.” It’s amazing how that will drive you, although it makes it a little more difficult to be purely analytical about your decisions.

Why leave Real Food Works for Monetate? I know that surprised a lot of people. It did surprise a lot of people. There was a push and pull. The push was that we had come to the realization that Real Food Works is what we call a cash-flow or lifestyle business. And it doesn’t operate at the pace that I’m best at. It just naturally has more of a slower, more gradual pace. The pull was, I’d been involved with Monetate since before its founding. I had been very close to the company. I have dear friends who are involved in it. It was a matter of coming to another company that I loved, and it had a new set of things to learn. I hadn’t grown a company through this stage before, so it had some real challenges and opportunities for me to grow as well.

You’ve said you want to teach CEOs at some point in your career. What would be your first lesson? It’s all about people. How do you develop people? How do you select people? How do you lead people? How do you motivate people? How do you help people self-actualize? As entrepreneurs, you get really caught up with product. Then we get very competitive and worry about sales and bookings — but at the end of the day, it’s people that drive all of it.

Published as “The BizPhilly Interview” in the January 2016 issue of Philadelphia magazine.

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