From helping Gen Z navigate their first tax filings to leveraging AI-powered tools for real-time tax support, Jill shares how H&R Block is making tax season easier, smarter, and more accessible for all.

"There’s a tendency to want to do more. I love the opportunity to test, learn, and encourage my team to take risks—fail fast, learn fast. But slowing down to speed up is more important than ever in today’s environment, where marketers have so many options to be really thoughtful." - Jill Cress

For 70 years, H&R Block has been a trusted name in tax preparation. Today, it’s far more than a seasonal brand—it’s a year-round financial partner. With AI transforming the tax experience, new IRS regulations shifting the filing landscape, and Gen Z entering the tax system with a unique financial outlook, H&R Block is evolving to meet consumers where they are. Jill Cress dives into how the company is bridging the gap between self-service tax tools and expert human guidance. From AI-powered tax assistance that supports taxpayers 24/7 to initiatives that maximize refunds and drive financial literacy, H&R Block is making tax season less daunting and more rewarding.

Jill Cress is the Chief Marketing & Experience Officer at H&R Block, where she leads brand transformation and consumer engagement strategies. With a background at Mastercard and Venmo, Jill brings deep expertise in financial services, digital marketing, and consumer behavior. She is focused on using technology to simplify tax filing, improve financial literacy, and help consumers make confident financial decisions.

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Tune into the latest episode or read the transcript below to learn more. Here are some top takeaways: 

Tax Season is the Ultimate Sprint
For H&R Block, the first four months of the year are a high-stakes marketing and operational push. With 150 million Americans required to file taxes, the brand must balance awareness, education, and acquisition in a short time. Jill shares how H&R Block optimizes campaigns, messaging, and digital experiences to meet customers where they are—whether in one of their 9,000 retail locations or through digital self-service tools.
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AI is Transforming DIY Tax Filing
More Americans than ever are opting to file their taxes themselves, and AI is making that process smoother. H&R Block’s AI Tax Assist helps answer tax questions in real-time—reducing stress, improving accuracy, and ensuring taxpayers get the maximum refund. With many people filing taxes late at night or outside business hours, AI-powered support is bridging the gap between self-service and expert human assistance.
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The Gen Z Taxpayer: Optimistic, Yet Facing Debt
Gen Z is entering the tax system with 30% more purchasing power than previous generations at their age, but they also carry significant debt. From student loans to buy-now-pay-later plans, this generation has a complex financial landscape to navigate. While they’re confident in their ability to earn—especially through side hustles and gig work—they need more guidance on tax deductions, savings strategies, and long-term financial health.
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H&R Block is Bringing Tax Education to TikTok
Most people don’t want to think about taxes year-round, so H&R Block is meeting them where they already spend time—through social media, gaming, and interactive content. The brand’s Minecraft integration with Sir Block and reality TV-style TikTok content makes financial education engaging for younger audiences. By embedding tax literacy into culture, H&R Block is changing how people learn about their finances.
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Maximizing Refunds: How H&R Block Helps Americans Find Hidden Money
Millions of Americans leave $1 billion in unclaimed deductions every year. Through programs like Second Look, which reviews past tax returns for missed credits, H&R Block is helping taxpayers recover lost refunds. The company is also launching Price Match, ensuring customers get the best possible deal when switching tax providers. These initiatives reinforce H&R Block’s commitment to financial empowerment and customer trust.