Lead a Successful Digital Transformation

Four experts share their experience

Lead a successful digital transformation

Four experts share their experience

According to Gartner, 91% of companies pursue some form of digital transformation, yet only 40% report successfully achieving it.

WordPress VIP gathered a panel of experts who’ve led successful digital transformations at large organizations to discuss strategies and tactics business leaders can adopt to set up their organizations for positive results.

This conversation took place on June 4, 2020, as a live virtual event. The comments have been edited for length and clarity. The panel was moderated by WordPress VIP’s Chief Revenue Officer, Jary Carter.


Lora Dennis, Senior Vice President of Digital Media, NBCUniversal Owned Television Stations

Lora Dennis is Senior Vice President of Digital Media for NBCUniversal Owned Television Stations, the division of NBCUniversal that includes 42 NBC and Telemundo stations, a regional news network and their associated websites and digital platforms, 2 national multicast networks, as well as LX, a new TV and streaming network designed for Gen Z and millennial audiences. A broadcast veteran with more than 25 years of local news experience, in her role, Dennis spearheads the editorial, design and product development strategy, audience development, marketing coordination and business operations for all station and local networks’ websites, mobile apps, social and distributed platforms. She also oversees the division’s digital news team which supports the NBC-owned stations and regional news network, and a product development team that is charged with building and maintaining all local stations’ digital products.

Dennis is a recipient of the Alfred I. du Pont Silver Baton Award, American Women in Radio and Television Gracie Award, and 2015 Cynopsis “Top Women in Digital” Award. She earned a bachelor’s degree in Journalism from the Medill School of Journalism at Northwestern University. She resides in Westchester County, New York with her husband and daughter.

Jonathan Rivers, Chief Technology Officer, Fortune Magazine

Jonathan Rivers is an evangelist of customer-centric design with over 15 years building digital content, advertising and video technology. Prior to joining Fortune as their first Chief Technology Officer, he was CTO at 3Pillar Global, a product development services company where he lead their global product, design and engineering groups. Jonathan has also served as the Interim CTO at Telegraph Media Group where he oversaw the launch of Telegraph Travel, their successful eCommerce platform. As Sr. Director of Web Operations and Customer Support at PBS, Jonathan helped transform PBS into a digital leader building out their DevOps teams and Cloud Infrastructure platform. Earlier in his career, Rivers was Executive Vice President of AdJuggler, a digital ad-serving platform.

Nancy Cassutt, Managing Director, News, Marketplace (American Public Media)

Nancy Cassutt is a media executive with extensive experience in journalism and newsroom leadership. She was on the front lines helping transform newsrooms across the country as the digital age changed the media landscape. Currently, Nancy is the Managing Director of News for Marketplace, a non-profit business and economic news organization on a mission to raise the economic intelligence of the country.

Cassutt’s extensive journalism career includes work in reporting, editing, and managing in television, radio and online. She is known for leading change as technology and disruptions in the news economy have altered every aspect of the journalism business.

Scott Morris, Senior Vice President of Technology and Innovation, Nexstar Media Group, Inc.

Scott Morris is a seasoned, cross-functional executive with a passion for growing businesses and solving complex challenges by bringing together people, technology, strategy, innovation, and process to drive growth, efficiency, and customer satisfaction. Successful track record as a digital transformation agent with executive roles across industries with a focus on content management and syndication, video solutions, system architecture, UX/CX, full lifecycle SDLC, and digital security, data privacy, and strategies.

Scott is part of the Nexstar Digital leadership team with a mission to grow audience and revenue through better products, content strategy, and Audience & Business Intelligence that support the needs of product, content, and revenue.

Let’s get started with a brief introduction from everyone. Lora, will you kick us off?

Lora Dennis: I’ve spent the last 20 years at NBCUniversal working on digital transformation. During that time, I’ve seen my group go from 10 small websites to 17 platforms and being very mobile-driven. It’s been incredible to see the growth that’s happened in digital.

Jonathan Rivers: Howdy, everybody, I’m Jonathan Rivers, CTO at Fortune. I’m now on my third digital transformation job. Previously, I was at PBS where I built out our cloud infrastructure along with mobile applications and a full suite of products. From there, I went to the Telegraph in London where we re-platformed their entire website, as well as launched their first e-commerce business. And now I am fortunate enough to be here at Fortune to build out all of our digital pipeline.

Nancy Cassutt: I am currently managing director for Marketplace, which is a business and economics show, part of American Public Media. I’ve been in the news business for more than 30 years. For the last 10 years, I’ve been working with brands, both local and national, to help them figure out their editorial and digital strategies. This job is never done and we’re learning every day.

Scott Morris: I’m SVP of technology and innovation for Nexstar. It’s one of the largest media companies no one’s ever heard of. I’ve been doing digital transformation since the late ‘90s, mostly media, but also in the government space as well as the intelligence community. I’ve done work in real estate, and healthcare, and finance. Most of it has been with content management systems and creating user experiences that help change industries. I try to use that perspective to understand the challenges each of these industries are facing.

“Anything that’s done halfway never accomplishes its goals.”

— Scott Morris, SVP, Nexstar

What have been your keys to success
in digital transformation?

Lora Dennis: There are two character traits I’ve tried to embrace: perseverance and passion. Passion is important because we are often cheerleaders of bringing people along and learning new platforms, new technologies. And digital transformation can be a Sisyphean task. You make progress, then you feel like you’re slipping back a little bit. But perseverance is crucial, and having a 30,000-foot view to see the significant progress you do make.

There’s a saying that digital transformation is 20% technology and 80% business process. Fact or fiction?

Jonathan Rivers: I argue digital transformation is 100% change management and 0% technology. What you’re building? Not important at all. The technology that you use? Also not important.

What’s important are two things.

The first is hyper customer-centricity. Everything you do, you need to approach with the customer in mind. And when I say that, that means both your internal customers and your external customers. Everything you’re doing, every decision you make, you have to ask, are you doing something for them? Or are you doing something to them? And if you’re doing something to them, your internal customers will resist you with every fiber of their being.

External customers will walk away and go do something else. This isn’t the Mad Men era. You have to provide people products they want, not products you tell them they’re supposed to have.

Two, understand that change is hard. When we talk about change management, you need to understand you are from your organization’s future. And when you come in and start talking about the changes that need to be made, they’re going to look at you like you are some crazy internet space wizard, and you are speaking some foreign language no one has ever heard. And you have to be respectful of that.

Because if you do “change” for a living, you are comfortable with it. But this is new and scary for others. People have to give up 10, 20 years of experience to go do something new, which is an incredibly frightening prospect. And if you are not respectful of the growth you’re asking of people, you’re going to fail. You’re going to come across as arrogant, as condescending; you’re not going to get buy-in, your ideas are going to be rejected.

If change were easier, more of us would do it more often. Give your organization something to believe in. That’s key to anything going well.

Nancy Cassutt: I went to the school of change management hard knocks because I ended up leading a digital operation, very focused on journalism, in the digital space, starting in 2000. Two things I’ve learned—and I cannot emphasize how much I am still learning—one is, pick a team of movers who will help you move your organization forward. In other words, “Who are my body doubles?” so you’re not always the mouthpiece on it.

Two is over-communication. You can never say this stuff enough.

What’s that marketing phrase? You have to say it seven times before people get it. That’s true. And considering when they’re ready to receive that message is also really important.

“You don’t have to build everything from scratch. Leverage other people’s ideas and products they’ve built.”

— Nancy Cassutt

What challenges and pitfalls have you faced in your digital transformation journeys? Because you don’t get through this a few times without skinning your knees along the way.

Scott Morris: Too often, companies like to dip their toe in the water and just edge things forward. It’s a self-fulfilling prophecy to failure. So if you’re going to talk about “digital-first,” but not really do it, or design a mobile-first scenario but not really do that… if you’re not all in, you’re doomed to failure.

It’s really about committing and getting the business behind what you’re trying to do and going after the goals full force. Because once you do that, even when you run into the challenges, whether it’s budget or whatever, you can get to success if you can keep pushing forward.

Jonathan Rivers: My single biggest battle scar from doing digital transformation I’ve summed up with a pithy catchphrase, which is, “Don’t bring a design thinker to a deadline.” And I’m going to get a lot of hate for talking trash about design thinking. That’s okay, I’m a big kid, I can take it.

But here’s the thing: when you go to do transformation or engage in any level of innovation, you need to understand what you’re trying to get out of it and what your timeline is. And if you don’t understand those two things, you will never be successful. For years I’ve talked to all of my developers about the stack of dollars metaphor.

Imagine a stack of dollars on the table. Every decision you make, every feature you implement, everything you do is taking dollars off that stack. And if the things you build don’t start putting dollars back on that stack faster than you take them off, you’re sunk.

Things go astray where it’s pointless innovation or iteration. “I have two years, this is how much funding I have.” From there, how do I back that out into a very real plan? Because otherwise you’ll just get trapped in the morass.

Nancy Cassutt: The timeline thing is so crucial. Figure out how much time you have and then back-time yourself.

But I would also say, you don’t have to build everything from scratch. That’s something I think everyone thought: Only we can do this. Leverage other people’s ideas and products they’ve built. And even before you build it, figure out who your audience is. What are you trying to do? I’ve made plenty of mistakes on that.

Lora Dennis: We have lots of stakeholders who will be like, “Oh, I saw this new platform, or I talked to this vendor; can we do this?” And you have to stay true to your product roadmap, and what it means to the business, and how it helps them as internal stakeholders. So when the bright, shiny objects come in, you can filter it through: “Does that align with what we’re trying to achieve, yes or no?”

The other part is putting real parameters and rigor around your testing and evaluation of new platforms and products. And not just launching something and saying, “Okay, so now we’re on Roku or now we’re on Google Home.” But saying, “Okay, what kind of growth do we want to have? And where are we in three months?

And are we involving the product? What is it? Is it really what we want it to be? And maybe it’s time we take that off of our product suite.” That’s an area we haven’t done enough of in the past. And we’re trying to focus on that now.

“If you do ‘change’ for a living, you are comfortable with it. But this is new and scary for others. And if you are not respectful of the growth you’re asking of people, you’re going to fail.”

— Jonathan Rivers

How do you prioritize the user experience as you go through digital transformation? And let’s define that in two ways: internal stakeholders and your end customers.

Nancy Cassutt: I come from public media and our audience, our customers, really want to be close to us. They love our talent, they love our content, and they want to engage. They give us money, so they feel they (and truth be told, they do) own us in a way. So how do we serve them and keep them close all at the same time?

The idea is, we leverage the WordPress platform we are now on, which we love by the way. We bring them in; do a very interactive engagement process where they’re leaving questions, we’re answering them on the air, we’re using their names… From that, we try to engage them with newsletters, things probably many of you do.

Ultimately for us—and it is a journey—is to eventually turn them into what we call “investors” in Marketplace. We want to make sure, yes, we’re interacting with you on the content side, we’re engaging with you, we’re listening to you. But we also ultimately say, “Do you want to invest in us further?”

Jonathan Rivers: I’ll tackle the internal question because I think it gets overlooked so often. And it comes back to talking not about what are you going to do, but why are you going to do it? And what are the outcomes you expect if you are successful? Why are you disrupting their life? If somebody has used one particular CMS for 10 years and you go to change it, you’re going to get resistance because you’ve just invalidated 10 years of experience. So talk to them about why you are making the changes. At the Telegraph, we rewrote our authoring system. At the time, it took 81 steps and 55 minutes to publish a piece of content. They rewrote it and got it down to 20 steps and 30 minutes.

Why did we do that? Well, think about the efficiency of scale, think about the amount of content that can come out. Think about the quality of the content. Get them to buy into the process, rather than just handing them a fully baked solution. You don’t go do this stuff in silence and two years later pop out a system. You have to get all of your customers, internal or external, involved in it.

And the other thing… It’s a bit of a rant I do all of the time, but I think it matters so very much for this. Stop using the word user. Just stop using the word user. It’s horribly offensive; it denigrates all humans into machine operators. I have customers.

They are in finance, they are a writer, they are an artist, they are a product manager, they are an account manager, they are a human being who wants to create.

People do not exist to use the systems. And when you treat people like they exist to use the systems, that’s how they’re going to react back to you. Instead, approach them with, “this is how we’re going to create, this is how we’re going to bring things to market so we can do the things we love and believe in,” rather than clicking around on screens. You’re going to get much, much better results.

“Give your organization something to believe in. That’s key to anything going well.”

— Jonathan Rivers

When you evaluated your digital experience platform, what did you find in the market?

Lora Dennis: We embarked a couple of years ago on moving to a new CMS. When we first moved off of Internet Broadcast, and we took over our websites, we had 10 websites and no real mobile products. We outsourced mobile. So we were on 17 platforms. We’d outgrown our content management system.

In this work, there are lots of things you do that are sexy and content management systems frankly aren’t. But they’re the most important infrastructure. It would be like you’re going to build a house, but your foundation doesn’t work.

And to be honest, for us it was a real barrier to getting content creation from our larger newsrooms because it was just not intuitive. So we evaluated 10 CMSs; got it down to four. It came down to Drupal and WordPress. And by nature of the fact that we have hundreds, now thousands, of people creating content across our division, we landed on WordPress.

We launched in December and by mid-January, some of our stations had gone from having a handful, maybe 15%, 20% of the people contributing regularly to numbers up toward 50%. I never would have thought it would happen that quickly. But that speaks to something I think is important is there was buy-in from the leadership, and there was training and support from our teams.

That combination is so important to make sure these platforms are working. We’ve joked nobody loves their CMS, but right now, we love our CMS.

Jonathan Rivers: I’d say beware of the one-stop-shop. You know, any platform that claims to do it all, probably doesn’t do it very well. If you get seduced by that sales pitch, you’re going to find places where it’s woefully inadequate for the things you want and need. Going into it, look for best of breed solutions and then know you’re going to have to stitch them together. Make sure your business customers are involved in that process. What it absolutely can’t be is an IT exercise.

RFPs are a horrible way to do anything because it reduces everything down to a spreadsheet. And somebody in IT is going to go, “Okay, these four platforms have the most checked boxes in my spreadsheet at the lowest price; we’re going to buy that.” I promise you, that is a digital transformation that is going to fail in a heartbeat because it was based on price and somebody who didn’t know what they were doing, making the selection. And so instead, identify the systems or capabilities that are most critical for getting your content and your message out, pick those, and then build connectivity between them to integrate it into an ecosystem, rather than just trying to buy an ecosystem out of the box.

What concepts or technologies are you seeing
in the market that are more hype than reality?

Jonathan Rivers: I think AI is heavily overrated. And I’ll tell you why. Because I think personalization is antithetical to customer-centricity. And by that I mean, AI is only good at knowing what people want or what they liked and giving them more of that. That doesn’t challenge them, that doesn’t inform them, that doesn’t create any value other than just consumption.

Scott Morris: Jonathan, I don’t disagree with the premise of what you’re saying. AI, to this point in time, has been a bit overhyped.

The Facebooks of the world feed you what you want to hear. They want you to come back, so they’re reinforcing your biases or your bubble view of what’s happening in the world. And that drives us further apart, so that’s a terrible experience.

But, AI is more than that. As a for-profit media company, we’re matchmakers. We’re trying to introduce advertisers to customers.

And to do that, we have to have the best product and then the best way of monetizing that product. And AI helps us do that if we’re using the right data correctly and using it in a tactical and practical way.

“There are lots of things [we]
do that are sexy and content management systems frankly aren’t. But they’re the most important infrastructure.”

— Lora Dennis

Do you see digital transformation accelerated due to the current pandemic? And what piece of advice
do you have for companies who have to do it overnight, versus a timeline of two years?

Lora Dennis: For my digital team, we’re very comfortable working remotely. For others, it’s not as comfortable. So the tools we use, we’re introducing to other parts of our company. Obviously, change is hard. And these are the worst possible circumstances for remote working because you’ve got your kids at home, you can’t leave your house, you have anxiety around what’s happening…

But we try to ask, what things are we doing now that we can do longer term for the benefit of the company?

There is a tool I use called the snowman. So its vision, strategy, and operations, and being able to have all three of those. And right now, people are in operation mode, but you have to be able to get out of the weeds and look at strategy and vision to see how what you’re doing is going to apply to your longer-term objectives in the company.

Jonathan Rivers: This more than any time is the one to remember: not to let perfect be the enemy of the good. For true innovation, you can’t have everything be perfect every time. You have to be willing to experiment; you just have to be willing to try and do it. When people are open and hungry and ready is the best opportunity to ever do that.

Why is doing digital transformation piecemeal a bad idea? How is that different from being iterative?

Scott Morris: We’re a for-profit business, so there’s a tendency to be like, “Well, let’s go two inches in this direction.” And you can’t do that. You have to have a long term vision of where the market’s going.

And truthfully today’s world is changing faster than ever. So what does that look like five years from now, 10 years from now? And then have a plan to get there. You’ll launch MVPs, and you’ll iterate on them, and you’ll get things wrong, and you should fail first and learn from that, and move on. You need to have a game plan and a roadmap to get to the end goal and have the budget and the wherewithal to go after it.

Key takeaways

With an undertaking as complex as digital transformation, there
is no one-size-fits-all solution. The right strategy depends on your industry, your business goals, your budget, your timeline, and more. However, as our panelists shared, there are best practices to keep in mind, no matter what stage of the digital transformation journey you’re in.

  1. Pre-define your budget, timeline, and milestones
  2. Incorporate your internal customers from the very beginning
  3. Remember, 80% of change management is the people factor
  4. Create a clear product roadmap to test new ideas against
  5. Incorporate a rigorous testing program into your
    decision making
  6. Know you don’t need to build everything from scratch
  7. Beware of the one-stop-shop in purchasing decisions
  8. Avoid making any decisions in a vacuum
  9. Overcommunicate with both internal and
    external stakeholders
  10. Celebrate the small wins along the way

WordPress VIP is passionate about helping large organizations build transformational digital experiences for their customers. If you’d like to discuss any of the ideas presented here, please get in touch.

Get the ebook

Fill out the form below to receive a link to the ebook in your inbox.