Digital 2.0 – The Modern Digital Executive

People, Stories, and Integrity: Why They Matter More Than Technology

Author: Geremy Reiner , Associate Principal, Prime TSR

Tech leaders talk a lot about tools and processes. They especially love to bandy about the phrase “digital transformation” when strategizing for ways to drive organizations forward. But Lori Gustafson, Chief Brand & Digital Officer of Marriott Vacations Worldwide, defines digital transformation differently.

Meet Lori Gustafson

Tech leaders talk a lot about tools and processes. They especially love to bandy about the phrase “digital transformation” when strategizing for ways to drive organizations forward. But Lori Gustafson, Chief Brand & Digital Officer of Marriott Vacations Worldwide, defines digital transformation differently. 

Lori has served as an account and digital solutions executive for an impressive organizational roster. She’s served Relevant Media Group, MindComet Corporation, Darden Restaurants, Seaworld, and many others.

For the last two years, she’s headed up branding and digital growth for Marriott Vacations Worldwide, a company boasting 120 global vacation resorts with nearly 700,000 owners.

Lori’s a technologist. She knows digital. And her resume proves it. In fact, she has devoted nearly two decades of her career to digital marketing. Yet, when you stand Lori beside other digital executives, she stands out. Her perspective is fresh—and if you listen to our interview, you’ll see what I mean.

During our 30-minute conversation, Lori and I covered a lot of ground. We tackled everything from how she defines leadership, why vision matters more than technology, why leaders must be adept storytellers, and more.

Here’s what she had to say.

Biggest Lessons Learned About Transforming Companies Digitally

“Everyone’s talking about digital. What about mindset? Why aren’t we talking about that?” That’s what Lori said when I asked her what she has learned after 20 years of transforming organizations.

Technology is powerful. Lori knows that. Yet, she argues that digital processes aren’t “what’s going to help you drive your organization and do significant things.” Mindset will.

The world presents itself as it is. Our mindset shapes how we, and others, interpret it. That, Lori says, is a superpower.

“If you want to change people’s habits,” she says, “especially those who are well-tenured, you don’t give them tools or processes.” No, you must shift their mindset and help them see the bigger picture. That’s the only way they’ll join you on the journey.

Mindset is one transformational ingredient. Collaboration is another.

You may have a vision, but you need others to realize it. Want to transform your company? Lori suggests finding early adopters you trust—people who will “co-create and champion that vision across the organization.” They’ll socialize your quick wins and ensure you maintain the inertia necessary to drive your transformational program forward.

How Lori Defines Innovation

Innovation isn’t about digitizing an antiquated process. “It’s about reimagining what’s possible—then moving beyond what exists.” That’s how Lori sees it.

In Lori’s experience, when people say “digital innovation,” they’re usually talking about using technology to streamline functions, bring new consumer products to market, and change business models. Sure, that’s part of it, but as Lori points out, something critical is missing from the conversation: people.

We have to include people in the conversation when we talk about innovation.

We can innovate all day. But if we aren’t delighting customers and team members in the process, we’ve failed. For Lori, digital is an enabler—a bold ambition. But it’s not an end.

“I don’t want to lose high-touch moments or opportunities to delight our guests just for the sake of innovation,” she says.

“I care about how our associates deliver on that, too. So whether you’re working in a call center, managing AI chatbots, or delivering a frontline experience for guests, I want to ensure we’re deliberately empowering people with the right tools and solutions.”

Biggest Impact on Digital Innovation For The Next 10 Years

I was curious about what Lori believes will have the most significant impact on innovation in the next decade. “The ability to simultaneously perform and transform.” That was her answer.

To perform and transform at the same time is a balancing act. Yet, Lori argues it’s one that must be mastered. Why? Performance earns credibility. Credibility earns trust. You’ll never get permission to innovate and transform without credibility and trust.

You’ll also increase your success rate with some good old-fashioned listening and storytelling.

Listen and Learn
Lori suggests embarking on a listening and learning tour. Talk to the top 50 or 100 individuals across your organization. Find out what they do, ask them what would make their lives better, and find out what they think customers want.

Capture those answers and then distill them, says Lori. That will uncover your core organizational needs and give your vision direction.

Master the Art of Storytelling
Want to secure employee buy-in and drive your vision? Then you must tell a compelling story.

Compelling storytellers are empathetic and understand their audience. More importantly, they’re able to imagine themselves in the lives of others. If you want to appeal to those with decision-making capabilities, Lori says, you have to appeal to their experiences, desires, and pain points.

The best way to do that? Storytelling.

Digital 2.0 Hot Seat: Real, Hype, Or WTF

I closed our conversation with a series of rapid-fire questions covering four of my favorite topics: AI, the Metaverse, Crypto, and remote/hybrid work.

Here’s what Lori had to say.

AI – Hype, Real, or WTF?
“Real—and coming. I still think we’re a few years off from realizing full potential, but there’s going to be major upside once we do.”

Metaverse – Hype, Real, or WTF?
“A little bit of hype, a little bit of real, and a little bit WTF. Based on the sheer investment numbers the technology companies are pouring into it, I believe it will ultimately be a realized vision. What that vision is, I don’t know.”

Crypto – Hype, Real, or WTF?
“Crypto is in a hype stage right now. It’s early, so it’s hard to predict its impact. But I do think it will eventually be a mainstay.”

Remote/Hybrid Work – Hype, Real, or WTF?
“Here to stay. Current and next-generation workers expect an adaptable working framework. That said, the industry impacts the remote model. Hospitality requires people to be on-site—at least for now. I do envision a day in which robots check in guests. But until then, we’ll be on-site doing our jobs.”

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