H&R Block’s Jill Cress on AI, Digital Tax Filing & Brand Relevance

Hi, Matt. So great to be here. Thank you for having me.

Absolutely. It was an incredible opportunity to grow as the industry was evolving and fintech was becoming what it is today. In the 20 plus years I was at Mastercard, when I joined it was a not-for-profit association.

Yeah. An association of bank issuers and merchant acquirers. And we were really connecting buyers and sellers through that network. We then became for-profit and then we had the push towards a quite successful IPO and then had the time working there after the IPO where Mastercard really embraced the data and knowledge that it had on consumer behavior to diversify its business. And it was an amazing place to grow up as an executive and also as a human being. It really allowed me to grow in so many ways.

Yeah. Again, I feel really fortunate in that Mastercard was a very supportive environment for me in the way that I thought about my development. And I think I was pretty intentional about wanting to continue to grow, to take on expanded roles. I did lots of zigging and zagging and taking, you know, moving horizontally across the company, moving geographically. And I think being clear on what it is that you're looking for and if you're fortunate enough to work in a culture that is supportive of that growth and you can find ways to grow. Mastercard was a growing company. It was on the precipice of lots of new things over the course of my tenure there. I joined to launch debit cards which were nascent at the time. I then was actively involved in launching some of the very first co-branded cards in the world. I had an opportunity to move to Europe where I worked on mobile payments and leapfrogging the gap in technology that existed in Europe through telecom infrastructure. And so there was always something new and challenging and that created a really interesting playground for me to take risks and to learn. So I feel fortunate that I was able to grow there. In the 22 plus years I was there, I think I had 13 roles: local roles, regional roles, global roles, strategy, product, marketing. So it was a really robust environment for me to grow and make an impact.

Yeah. Well, I think it's really broader than you know. We, it was credit card was the category. Right now it's payments and all the things that you referenced, the form factors and the ways to pay. Interestingly, when Apple Pay launched, a big part of what fueled an Apple Pay transaction was Mastercard technology. I actually worked on some of that. And then, you know, I detoured over to National Geographic and we can talk about that, but then I was at PayPal where mobile apps and driving more engagement and payment through those apps was the value prop that we brought to the market. And it was interesting. I think that there were a few things that were happening that were driving large-scale adoption of largely mobile to conduct transactions. The big one I think was what was happening in transit. In the UK, for example, when Oyster embraced mobile technology, you just saw a huge adoption of Apple Pay in the UK. I lived in the UK for a while and I was spending a lot of time there and to see the massive shift from what were prepaid Oyster cards to enable transit and entry into the tube to the proliferation of Apple Pay, to be a streamlined, significantly less friction, a frictionless experience. And similarly, I'm here in New York and you see it with New York Transit here as well. And so I think as mobile payments can facilitate a more seamless experience for consumers, you see much more adoption. And I think the beauty of being able to leave your home with just your phone, knowing that you have the ability to engage in commerce with it, is a really exciting thing for a lot of consumers who just want to have the phone as their primary device. I mean, there's all sorts of crazy data, right? People would rather lose many things than their phone.

Very, very sad statement, but you know, I think that the proliferation of phones. At H&R Block, we have launched a mobile banking app that is working hard to serve our hardworking Americans who need a solution that is less expensive than traditional banking. And we see when we add more utility through savings tools and things like that, offers discounts, we're really creating an experience that delights the consumer and creates a more sticky relationship with our brand. We enable payments through our mobile app through Mastercard. And as consumers do more on their phones, they're going to use those to pay more. And I think that is really the form factor that is winning and will continue to win.

Yeah. Very little.

Absolutely. We just bought a Rivian and there's no key in the Rivian. We use the app to open it. I suspect other electric vehicles are the same. So yes, it is very interesting. I travel a lot and so I often feel badly when I engage with someone who needs a tip and I'm not able to tip them because I don't have cash. Actually, when I was at PayPal, we worked on a QR code solution to facilitate gratuities, which I think was an interesting use case. The other thing that I will say, and this was really indicative of the time that I spent at PayPal, was COVID really accelerated the comfort that more consumers across different demographics had with mobile and electronic payments. We saw explosive growth. Everything had to be done via e-commerce and you had a whole new entrant of consumers who were embracing online shopping and learning how to use mobile banking apps and things like that.

That's right. They refer to it as the PayPal mafia, you know, Peter Thiel and Elon Musk and others who built that technology. And yes, then it was spun off and there was a separate IPO for PayPal as a standalone company.

It was a really exciting time to join PayPal as they were looking to do more than just facilitate commerce. And it did have a very, I guess I would say it was more of a tech-forward vibe, which I think felt startup-like to me. Certainly based on growing up at Mastercard, which while very technology-oriented, grew out of banking and felt a little more conservative from a culture standpoint. And then I was at National Geographic in the entertainment space. When I landed at PayPal, I found the energy to feel similar to the tech companies that I had partnered with, having spent time at Facebook or Google or other tech-forward companies. And so the energy was great. The then CEO Dan Schulman, who took PayPal and led the PayPal IPO in separation from eBay, he was not the founder but he had a founder-like energy to him and really worked hard to rally the troops, to inspire culture. And that's what made it an exciting time to be there because we were really working to expand, to do more jobs. We launched crypto while I was there, we launched installment products through our buy now, pay later boom as well. And so it was very much a swing for the fences culture, rallying technology resource and capacity around growth, and it was very energizing.

Yeah, so I received a call from a recruiter who had placed me before and he said, "I've got this great opportunity. You have to take a listen." And he said, "H&R Block." And I thought, "Huh, that's interesting. Taxes, Kansas City, I don't know." And he said it is a company that is very much in transformation, which is something I really enjoy. It was a big reason why I chose to leave Mastercard and go to National Geographic, which was a joint venture really going through a digital transformation. Anyway, I liked what the recruiter had to say. And so I met the CEO, Jeff Jones, who grew up as a very iconic marketer. He was the chief marketing and experience officer at Target. He worked at Gap, Coca-Cola, had a short stint at McDonald's. Very impressive. And very consumer-centric. And the thing that was really exciting was the transformation, the focus on the consumer, the focus on digital products and solutions and diversifying our product experience to do more jobs for our tax clients so that we could be a year-round company. It was the chief marketing and experience officer role, which I had had experience roles. I had had brand roles at PayPal. I learned growth marketing on an epic scale. At one point at the peak of our consumer growth there, we had 400 million consumer relationships around the world and we were really focusing on new client growth. So it was really this interesting opportunity to bring the things that I enjoyed doing—brand building, growth marketing, transformation, digital products, experience—into a role that was designed to do just that for a chief marketing and experience officer that had a seat at the table reporting directly to the CEO. And I am having such a great time. I am feeling so fortunate to be in this role, to be empowered to swing for the fences there, to take some bold risks as we work to really address what is a bit of a crisis of relevancy, which I find to be a huge opportunity from a brand experience standpoint, understanding the tailwinds and headwinds under brand reputation and how we can think about continuing to drive real transformation to win in this space. H&R Block built the tax category and we're here working to continue to energize it and revitalize our brand as the best way to facilitate that tax experience and do other things like provide those financial solutions through our mobile banking app and do more jobs for small businesses.

Yeah, absolutely. H&R Block is a nearly 70-year-old company. It was founded by two brothers, Henry and Richard, hence the H&R. Henry and Richard Block in Kansas City who observed that the tax experience is intimidating and overwhelming and that they could take some of the pain out of that and provide more help through creating a network of experts who could help to facilitate that. And we have really built our business around that purpose of providing help and inspiring confidence around this very challenging moment. As we sit here on April 4th, we are knee-deep in pushing towards the tax deadline of April 15th. Exactly. And so we built that expertise and care through building that human relationship. H&R Block has around 9,000 locations that are open during tax season and close to 60,000 humans that are facilitating that experience between client and an expert to facilitate the tax return. For most Americans, it is the most significant financial moment of the year. That's because 75% of Americans get a refund. And for many of them, it is a critical influx of cash or it can be a vehicle for creating savings for surprise and delight moments through the year. And our reputation was built on that human expertise in the retail experience. At the same time, as the world became more digital, and this really gets to the crisis of relevance, H&R Block launched really great digital tools and you can work with H&R Block and get that same expertise and care without the need to work with a human in a retail environment. The perception of consumers is you have such a strong retail presence that casts as, "Oh, this is the company that you go into their retail establishment on Main Street to get my taxes done." When people use digital and you're saying you do have that, there's just that lack of awareness or understanding.

That's exactly it. So we've got 90 plus percent awareness, 90 plus percent scores in trust, but that is very much associated with that retail experience. And so you can do the same thing with H&R Block as you can with our biggest competitor. You can do your taxes online and use virtual help and have access to a product we launched this year, an AI tax assist, which can bring that expertise. So we serve 20 million clients every year and about half of those are through the traditional tax expert experience in either retail or virtually as we're talking now through a virtual experience. And then we serve about 10 million through our digital product experience. And that is really the crisis of relevance: how can we continue to be known for more than just our legacy and really create awareness of the delightful digital experience that we can provide? And we really took the gloves off last year and decided to look at how great challenger brands have challenged the category and really started to take aim at the competition and actually use the equity that exists there in comprehension of what it means to do your taxes online in a trusted way, and we're starting to challenge the category.

Yeah, you're exactly right. And Walmart is a great example, Matt. I look very closely at Walmart, what Walmart is doing. William White is very inspiring. He's amazing. And another former Target exec. I think their approach to omni has been really inspiring and I take a lot of inspiration from the way that they have told their digital story through content, the way that they bring their UI into that and show the simplicity of it. And we are looking at brands like Walmart and others who have gone through that transformation to help inspire how we tell our story because that's really what it comes down to: breaking down those barriers and perception and getting people to consider us. And so our campaign this year is all about switching, making the switch to H&R Block. We reference the places you can switch from, largely our competition, whether that be an independent tax preparer or TurboTax.

For sure. Yes. And a lot of that has really come down to the thing that drives, I think, great brand positioning and product development, which is what is the data telling us? And so really looking at who's using and really delighted by H&R Block and where do we have an opportunity to grow. And so one of the things as we've been challenging the category and disrupting ourselves has been the effort that we have embarked on which is to win disproportionately with new entrants into the category, which is Gen Z. And working to understand what are the headwinds that we have with that audience from a perception standpoint and where do we need to meet them to introduce our brand in new, more relevant ways to get them to consider and choose us? And that has been rewarding in that we're moving the needle there. But it's also really inspiring our customer experience, marketing, and comms folks who sit within the world that I manage to try new things and we've had some fun with that.

Yes.

Yeah, we are really excited about the momentum and the fact that we are really operating at scale with an AI solution at this point. So we worked cross-functionally with our CIO and our product organization to look at what jobs could AI do for us. And at the same time, Microsoft and their Azure team were looking to partner with different companies to bring different use cases to life. So we were really delighted to be a part of a pilot program with Microsoft and to work with them leveraging their technology and understanding of large language models to bring our AI tax assist to the market. And it was a consumer experience that was envisioned through the things that we know matter to consumers, which is providing that expertise and answering questions in an easy and efficient way. And essentially what we've done is taken that corpus of knowledge of nearly 70 years of tax preparation and continued to build and train the model to answer the most basic questions in a way that makes the process more efficient, makes it easier for consumers, keeps them engaged in the product, and doesn't take them out of the product once they're in a chat experience and they need to get more information. So we had a big sprint to launch AI tax assist. It was a huge cross-functional effort with our team of designers, product, technology, and all those concerns that you have with financial information. I'm sure it was no small feat.

Absolutely. And yeah, so it's launched, it's live. We have seen really good engagement with certain audiences, Gen Z being one who very much is embracing AI and using that to facilitate that promise of our brand, which is we're bringing expertise and care to those clients in a way that is leveraging new technology to do that.

Yeah, I certainly never expected that. It was funny the other day TMZ referenced Responsibility Island and closed the segment saying, "It makes me want to do my taxes with H&R Block."

I think so. I mean, I certainly shared with my team and with our CEO two references that I didn't expect to live together in a positive way were H&R Block and TMZ. But here's where we were again, starting with the data, knowing that we had to win with Gen Z. Last tax season, we created a lot of short form content. We really embraced TikTok and we were able to meet that audience in ways that were fun but also educational and entertaining. And I think with so many things where we push boundaries as marketers, there is good fortune involved. So fortuitously, the writer strike served us really well in that while writers were not able to write properly for entertainment, they could work for brands. And an old friend who I had been trying to work with for years said, "Hey, I've got a bunch of writers who want to do some branded content while they can. Let's get in a writer's room and understand what your problems are and come back with some solutions." And that got us to Responsibility Island, which was again a data-driven approach looking at what kind of content Gen Z and younger millennials consume. They're all about Love Island and Love is Blind and other reality television. And the concept was, well, what if we can take some young people to an island under the guise that they're there to get lit and have a good time, but they're really there for a lesson in responsibility and the only way they can get off the island is to do their taxes. And so it was a four-part micro series, four or five minute episodes where we introduce a selection of young singles who are taking on some responsibility challenges like doing their own laundry and the penultimate experience that they have to do to get off the island is to do their own taxes. And so we introduce our online tax experience since we introduced AI tax assist. And it's been really fun. It's done a lot of jobs for us. We've launched it on Roku, YouTube, and our own website, and we are seeing really high engagement with it and conversion into our DIY product. So that's great. But the other job that it's doing for us is helping us to learn how to test responsibly, how to really look at an opportunity and challenge the status quo in the way that we've gotten at it and to embrace a learning journey and to take some risks. One of our values is to stay curious and to be bold. And so doing these things within measure is teaching our organization that it's okay to experiment and we need to test and learn as best we can.

Such a great question. What I've always been really curious about is consumer behavior. My dad worked at Quaker when I was quite young and I was really fascinated by advertising and the way that they launched new products and I dreamed of being a marketer. I was writing jingles since I could write. I studied marketing and when I graduated it was one of the previous recessions. I had a job with a CPG company in the beauty category. I was absolutely delighted and that offer was rescinded. I was gutted and I thought, "Here I am a college grad. What will I do?" And I actually started my career in banking. I worked at a regional bank in Chicago, which is where I am from, and I was learning commercial banking and making the best of it. And the CMO of the bank went on maternity leave and we were launching a Mastercard product and I raised my hand and said, "Can I work on that product while she is on maternity leave?" And that was a real pivot for me in helping me ultimately get to a role in marketing. I started working with Mastercard and ultimately that was my entree into working for them. And so it was not so much financial services as the thing I was passionate about. It was storytelling, value prop articulation, launching new products that really energized me. And I then just became really passionate about people's relationship with money and continue to choose places where I can bring that expertise that I have and continue to drive for differentiation and transformation.

Yeah, I love that question, Matt. I would say the first thing was consistently raising my hand. I do a lot of coaching and mentoring. That is very much core to my purpose and I always share the following: understand what you're really great at from a competency standpoint. Be clear about the things that you're passionate about and understand how those play into what matters at the enterprise that you're at. And it kind of makes a really nice little intersecting three circles. And when something matters to the enterprise, you're good at it, and you have passion for it, raise your hand and lean in. And that was really the thing that I did with a lot of confidence at Mastercard. It started with asking if I could fill in when the CMO took a maternity leave. Raise your hand. It doesn't always happen, but great advice. And I think if you do it through the lens of what matters to the enterprise and how you can bring value, you'll often get a fair hearing and create a path to doing a growth project or providing some sort of support in a task force, etc. So that would be the one thing. And then the other thing is, I know it sounds trite, but I took a lot of lateral moves to learn new skills and to be really looking at what's coming at the thing that you're doing and learning how to be great at it. When digital started to happen, I saw what was going to be possible in the way of consumer engagement and attention and consumption across new social channels. I was intimidated because I was not a digital marketer. I was more of a strategist. I was really great at value prop articulation, but I really pushed myself to be uncomfortable, to take on a digital marketing role. I worked on building Priceless.com when I was at Mastercard and I remember going to meetings with our agency and they said, "Okay, now we're going to look at wireframes," and I was like, "Oh my gosh, what's a wireframe?" So I think it's about being vulnerable but clear about where you need to grow and what you need to learn.