How do you lead when everything is changing? In this first installment in our new series of CMO profiles, Jill Cress explains how she’s weaving AI into H&R Block’s tool set and mindset.
There isn’t a playbook for CMOs to follow in the AI era, but a growing number are making progress that speaks for itself. Take Jill Cress.
As chief marketing and experience officer at H&R Block, Cress has spurred a 24% increase in the use of AI-powered marketing tools across her teams. She’s proud of the acceleration, but she doesn’t chalk it up to technological acumen alone. Rather, she says a disciplined strategy rooted in empathy and education has helped the tax prep brand blaze new trails in AI-driven personalization and precision.
Empathy meets strategy
Cress has always had a deep-rooted interest in human connection. Growing up in Chicago in the 1970s, she loved TV commercials and was fascinated to see how brands create emotional bonds with consumers, including at Quaker Oats, where her father worked.
In her marketing leadership career, Cress thrived on the strength of her own relationships, but she didn’t fully grasp their importance until she left Mastercard after 22 years and was overwhelmed with grateful correspondence from all the people she’d known there.
“I was flooded with this clear belief that, wow, this is the work. It’s about making people feel seen,” Cress says. “It’s about getting to know them. It’s about understanding what motivates them.”
We have to meet associates where they are in their learning journey specific to AI.
That may sound warm and fuzzy, but Cress’s people focus has been foundational to H&R Block’s marketing and customer experience. Under her leadership, the company has embraced a human-centered mindset as it weaves AI into its strategy and execution. This has required discipline.
“When AI first became the thing we were all obsessed with, we were promoting curiosity. It was like, OK, let’s do something,’” Cress says. But that initial enthusiasm quickly revealed a divide: AI evangelists were running full speed ahead, while others hesitated. To achieve greater parity, H&R Block launched a four-week AI training sprint with expert sessions and prizes, a program she credits for the 24% spike in her team’s utilization of AI-powered tools.
“We have to meet associates where they are in their learning journey specific to AI,” she explains. “There’s a quote I like to steal from my boss Jeff Jones, our CEO: ‘When met with resistance, teach.’”
Mapping AI to brand values
Cress is keenly focused on how AI tools can enhance H&R Block’s mission to deliver what she calls the Four Es: expertise, expectations, ease, and empathy.
“These are nonnegotiables in our brand,” she says. “Whether you’re meeting with a human, using us online, or doing a hybrid experience, those four principles have to show up.”
By adhering to these principles, Cress says, “We now have a much stronger orientation for how we use AI. That was a big unlock for us — it saved us from chasing AI for AI’s sake.”
With those values in mind, Cress’s team launched AI Tax Assist, a feature that allows customers using H&R Block’s DIY tax product to ask tax questions and receive immediate, expert-level responses at any time of day. The company sprinted hard to get AI Tax Assist live for the 2024 tax season, and the effort paid off with about 6% growth in the DIY product attributed to this tool.
We now have a much stronger orientation for how we use AI … . It saved us from chasing AI for AI’s sake.
AI is also supercharging the company’s marketing machine. By analyzing behavioral data and generating insights, Cress’s team is building more nuanced personas and tailoring messages for everyone, from newlyweds in their 20s to busy dual-income households.
“There’s real utility in using AI to do more interesting things with personas,” she says. “Delivering expertise to someone who is Gen Z looks different from serving a more mature client.”
Scaling personalization
Perhaps the most exciting AI breakthrough at H&R Block has to do with regional marketing efforts. Because taxes are personal, the company often competes with neighborhood accountants. But with nearly 9,000 locations across the U.S., H&R Block’s tax professionals are also local, which AI has helped to demonstrate by putting its pros directly into content and ads.
“The use case for a national or global brand to leverage AI to compete locally is exciting,” she says. “We can even use localized imagery — rural backdrops instead of urban ones. I’m bullish based on what we’re seeing.”
The use case for a national or global brand to leverage AI to compete locally is exciting.
That optimism is laced with a healthy dose of realism. For all the hype around AI, Cress believes the key isn’t adopting the flashiest tech. Rather, it’s aligning use of AI with the business.
“When we started to evaluate how AI could help us support customers, it became easier for our associates to use AI with intention,” she says.
It didn’t happen overnight, but this strategic rigor combined with individualized learning has allowed Cress to accelerate the use of AI in H&R Block’s marketing efforts. By leaning into empathy and core principles, her leadership approach offers a valuable example for CMOs everywhere who are seeking to define what it means to lead in the AI era.
