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May 15, 2025 45 mins

In this episode of The Intersect, I sit down with Katherine "KVJ" von Jan, veteran of big tech and co-founder/CEO of Tough Day, a company that’s built something quite remarkable: Tuffy, an AI-powered workplace resilience coach.

As traditional management structures have evolved, how can our work environments be healthier and more effective? We discuss how the middle manager role has become unsustainable and why so many employees at every level are feeling disempowered. In a world where burnout is epidemic, KVJ offers a hopeful vision for how AI might actually help us become more human at work.

Topics Covered:

  • How AI can assist both employees and managers with feedback, prep, and difficult conversations.
  • The rise of “un-bossing,” which centers on disrupting traditional management hierarchies, empowering employees to self-manage, and prioritizing mentorship in the workplace.
  • The power of AI “resilience partners” to not only help people navigate workplace challenges, but also learn new workplace skills.  
  • How Gen Z is redefining what leadership and work culture look like today, and how management will change in the future.


About Katherine von Jan

Katherine "KVJ" von Jan is the co-founder and CEO of Tough Day, an AI-driven company focused on empowering employees to overcome challenges and thrive in a "manager-light" workplace. Prior to Tough Day, she was Chief Strategy Officer, Innovation at Salesforce. KVJ is a fearless advocate for a human-centered approach to building culture, trust, and success leveraging emerging technologies. Her views have been shared broadly in media including CNBC, Forbes, Fortune, Wall Street Journal, and Wired Magazine. A global citizen and avid explorer, KVJ calls NYC her basecamp.

Follow Katherine "KVJ" von Jan on Instagram at @katherinevonjan


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