H&R Block CMO Jill Cress on using AI as a retention engine

For Americans, tax season can be the most significant financial moment of the year. For many, it’s also incredibly taxing (ironically).

In 2024, H&R Block became pioneers when the company introduced AI Tax Assist to help navigate what can be a complex process. The AI-powered tool adds a new layer between H&R’s chatbots and human tax pros. AI Tax Assist intelligently answers questions to cut down tax preparation time while improving accuracy, completion rates and customer satisfaction.

Now entering its third tax season, the tool has delivered meaningful lifts in conversions and retainment — and opened the door for even broader AI-driven experimentation across H&R Block’s marketing, content workflows and omnichannel strategy.

Ahead of the 2026 tax season, H&R Block CMO Jill Cress sat down with The Current to discuss why the company leaned into large language models early, how AI is reshaping the brand’s tone, personalization and local relevance, and the initial results from AI Tax Assist.

The conversation has been edited for length and clarity.

When H&R introduced its AI Tax Assist in 2024, it was one of the first brands to jump into the space and use AI to upgrade its customer experience platform. What was the catalyst behind the initiative?

So the program is very intuitive, but inevitably, humans have questions, and pre-AI, we had a chatbot to help, but if it couldn't get you as far as you wanted, you would have to call a call center to speak with a human. With the advent of large language models, we introduced this layer, called our AI Assist, which sits between the chatbot and the human, and we trained it to answer the most commonly asked questions.

It's driven a much better customer experience for our clients who are doing their taxes themselves because many of them are doing them at odd hours. I'm always amazed to look at the start times when people log on. Some people start at midnight, or two or three in the morning, depending on when they have a free moment. Once you start, you want to see your end result. And if you get stuck and the chatbot can't answer your question, and you can't get a live human because we don't have 24/7 assistance — we lose customers who don't complete the process.

How has H&R Block’s AI Tax Assist been performing thus far?

It’s been a real game changer, resulting in a 13% higher conversion for consumers who use it. It has a 95% accuracy rate and has allowed us to contain 96% of clients who tried the experience, contributing to 6% of its growth. This will be the third tax season.

How has H&R Block integrated AI into its marketing?

AI is really critical in driving more efficient marketing, particularly when it comes to content. One of the things we've implemented is Writer, a content creation platform. We're able to train agents with our brand voice and integrate it into our workflows to ensure that it is compliant and efficient with legal approvals. Consistency of brand tone and voice is critical to building trust. It also allows us to think about the tone of voice based on where a particular client or prospect might be.

We are in such a seasonal business, so we're ramping up the various use cases and the agents we're building to be able to create content that's more personalized, more localized, and we're really starting to see the fruits of getting our teams to use it as we go into tax season in January.

Can you share an example of AI at play?

One really great example is need-states around specific life stages. If you are newly married and you've just bought a house or you're thinking about starting a family and having a baby — those are all moments that can impact your tax outcome. But where people live has a big impact on their outlook, their financial outlook and how they see the world. What we're able to do is really leverage AI to speak about local nuances and considerations, especially because different states have different tax rules.

We're just getting started with that, but I think that's where the opportunity to leverage insights, data and AI to create something that resonates with audiences because it's less generic, and so powerful.

And how do you make sure creativity doesn't get lost in all this data? A brand like H&R Block must work with a ton of first-party data.

A lot of it is who do we want to win with? What is the core creative idea? And then allowing AI to leverage that idea at scale with human intervention to ensure that the brand guidelines are being adhered to.

H&R Block has an omnichannel marketing strategy as well. Are there channels that you are looking to experiment with implementing AI?

One of the areas I'm excited about is digital out of home using data and some of the location based opportunities that I just referenced, as well as using other digital display units to become more personalized based on knowing where someone is either from a life stage moment or from a geographic standpoint.

H&R Block is generally within five miles of every American. We have 9,000 locations, so we use that as a broad message to reinforce that proximity. We’ve seen significant positive results leveraging geo-based messaging. We did a test in Chicago two years ago where we were able to really customize a message for the public transportation system there. We would say there's an H&R block three stops down on a particular subway line because proximity and convenience really matter, and that drives that message home.

What does the brand want to do more of as it looks to 2026?

H&R Block has an opportunity to become more relevant. We work really hard to insert our brand into culture. Life moments are tax moments. One really fun, very effective cultural hijack we did recently was we took a moment to celebrate the Taylor Swift and Travis Kelce engagement that rocked the world. The engagement ring is a taxable gift, so we really work to find those moments that bring taxes into the conversation in a fun and playful way.

When it was announced, we started to observe in our headquarters that people were not being productive, and so we asked our Chief People Officer to give our Kansas City-based employees the afternoon off to celebrate love. We ended up going viral and on Good Morning America with a billion impressions. In the week following, applications for jobs at H&R Block were up 95%.