Jill Cress: Embracing Curiosity and Building Relationships
How can a theater background help a communications professional? You’re about to find out.
In this latest episode of the WomenHeard: Changemakers podcast, host Georgia Galanoudis speaks with Jill Cress, Chief Marketing & Experience Officer at H&R Block, a leader in tax preparation services. A 2024 Matrix Awards honoree, Cress’s extensive brand experience also includes PayPal, National Geographic, and MasterCard. Today at H&R Block, Cress leads a diverse team of customer experience, marketing, and communications professionals.
Here are a few key takeaways from the conversation.
Curiosity as a Guiding Principle
For Cress, curiosity isn’t just a personal trait—it’s a leadership philosophy. Whether navigating a new cultural environment, testing innovative AI solutions, or leading through challenging times, she emphasizes the importance of being open-minded and eager to understand others.
Her sense of curiosity has deep roots. Growing up, Cress was inspired by the strong, career-focused women in her family who defied traditional expectations. Watching their journeys shaped her perspective and sparked a passion for exploration. Cress reflects on how those early experiences ignited her drive to push boundaries, embrace the unexpected, and create inclusive spaces where people feel valued.
Curiosity, she explains, is also about asking the right questions. “What job are we doing for the consumer? Why do they care?” Cress emphasizes the importance of these fundamental questions for effective brand communication and customer connection.
The Theater of Leadership
Before embarking on her corporate career, Cress spent time in the world of theater—a background that continues to influence her approach to leadership. Theater taught her to be present, take risks, and embrace vulnerability, qualities she views as critical for women in leadership.
Theater teaches people to put themselves out there and show up, even when it feels uncomfortable. For leaders, especially women, she believes vulnerability is a strength that fosters trust and authenticity within teams. It’s about creating an environment where people can bring their full selves to the table.
Serving Customers with Purpose
At H&R Block, Cress leads a team committed to more than just tax preparation—they are helping hardworking Americans achieve financial freedom. She brings a deep understanding of what matters to customers.
“There are real lessons for us as brand marketers and those who study the art and science of communicating. We need to be really clear on who we’re serving and what jobs they need us to do,” Cress says.
This clarity extends to her leadership philosophy. In times of uncertainty, Cress believes that relationships are the foundation of any successful team. “Whatever the context is, whatever the setting that we’re operating in—ultimately, as leaders, we are in the business of building relationships,” she says.
Innovating with AI
Cress’s curiosity and leadership extend to H&R Block’s embrace of artificial intelligence. The company leveraged its 70 years of tax expertise to create an AI-driven solution capable of providing real-time answers to common questions, AI Tax Assist. This initiative represents more than just a technological upgrade, Cress says. It’s a thoughtful response to customer needs that serves as a tool for empowerment rather than mere experimentation.
By prioritizing purposeful innovation, Cress’s team exemplifies how AI can serve as a powerful tool for enhancing customer experiences while staying true to the company’s mission of making financial freedom accessible to all.
Tune in for Inspiration
From strategic marketing insights to lessons drawn from the political landscape, Cress’s journey is a testament to the power of curiosity, courage, and purpose-driven leadership. Her story underscores the importance of adapting to change and building meaningful relationships in every aspect of life.
Thank you to Jill Cress for joining us! For the full interview, listen to NYWICI’s WomenHeard podcast.
