Navigating the Messy Middle of AI with Alana Karen

What does the messy middle and making a career pivot have in common?

In this episode of Women Leaders on the Move, Natalie Benamou sits down with former Google executive and author Alana Karen to talk about why so many leaders are feeling the tension of AI right now.

Together, they explore what Alana calls the “messy middle,” where the pressure to move faster with AI is colliding with the reality of how people actually work, lead, and adapt. The conversation looks at the gap between AI hype and day-to-day execution, why leaders need hands-on experience with the tools they expect others to use, and how women can stay visible and grounded in a changing environment. Alana also shares why her own next chapter includes a portfolio career and a return to work that creates real-world impact.

About Alana Karen

An award-winning tech leader, author, and speaker with over 25 years in the industry, including two decades at Google. Led the development and scaling of teams and products that impacted billions of users globally. Her best-selling book has received awards, and a second edition, Navigating the Hard Tech Era, launched in 2025.

Learn more about Alana on her website.

HerCsuite® is a portfolio career and leadership network where women build what's next. Members land board roles, grow businesses, lead the AI conversation, and live their best portfolio career with our programs. Join us at HerCsuite.com, or connect with host Natalie Benamou on LinkedIn.