Cross-Functional Teams and Dedicated Problem Squads

Join us for a compelling conversation on leading through change with Karen Stroup, Chief Digital Officer at WEX. In this episode of The Data Chief, Karen shares her insights on navigating the complexities of AI adoption. She discusses why focusing on the customer problem is more important than simply applying new technology, how to build trust by accounting for the "human side" of data, and why her team uses a "two-way door decision" to combat the rapid pace of tech change. Discover her "hot take" on the future of analytics, where dashboards become a "backdrop" and an interactive, predictive experience takes center stage.

Key Moments:

• Navigating Ambiguity with People (06:02): Karen argues that leaders' primary role is to build confidence and help people navigate ambiguity. She explains that people fear the unknown more than change and suggests involving employees in the journey to help alleviate that fear.
• Trust and the Human Side of Data (14:30): She highlights that giving a correct answer is not the same as building confidence that it's the right answer. Karen discusses the importance of accounting for the "human side" of how people feel about the information they receive.
• Prioritizing AI use cases (22:48). Karen describes WEX's approach, which starts with a top-down cultural shift from the CEO, and then uses filters like value, feasibility, and desirability to prioritize projects.
• The "Two-Way Door Decision" for Technology (28:13): To combat the disconnect between rapid technology evolution and slow cultural change, Karen discusses using a "two-way door decision". This approach involves architecting solutions to be vendor-agnostic, allowing the company to pivot if a technology proves to be unsuccessful.
• "Hot Take" on the Future of Analytics (35:34): Karen's "hot take" is that the user experience will fundamentally change. She predicts that dashboards will become a "backdrop," while an interactive, predictive experience will move to the foreground.

Key Quotes:

• "Very few customers, whether it be a business or a consumer, say, I want an AI solution. What they're really saying is, I want the problem to be simpler." - Karen Stroup
• "Answering the question correctly is not the same as building confidence that it's the right answer to the question." - Karen Stroup
• "Being able to understand data, but in a way that resonates with them, is really important. I do think ThoughtSpot does this well in the sense that you may get one answer, and you say, 'Hey, can you explain that for me?' or 'Where does the data come from?' But that ability to 'peel the onion' is really important." - Karen Stroup

Mentions:

• WEX's Health and Benefits platform
• Agentic AI in Financial Services: The future of autonomous finance solutions
• Trillion Dollar Coach: The Leadership Playbook of Silicon Valley's Bill Campbell
• How Much Data Does a Ring Security Camera Use?

Guest Bio: 

Karen joined WEX in 2022 as Chief Digital Officer, a newly created role. She brings more than 15 years of experience leading product management, digital, and innovation organizations focused on software as a service offerings, primarily in financial services.

As Chief Digital Officer, Karen is responsible for expanding digital commerce opportunities by harnessing best-in-class product development, design, and digital transformation capabilities from across the enterprise. In addition to creating a unified strategic vision, she leads a team that executes against digital strategy initiatives and strives to create exceptional customer experiences by delivering new digital tools, platforms, and technologies.

Prior to WEX, Karen served as the Chief Digital Officer at Thomson Reuters. Prior to her role at Thomson Reuters, Karen served as SVP, Product and Innovation at Capital One Financial Services and VP, Product Management at Intuit.

Hear more from Cindi Howson here. Sponsored by ThoughtSpot.