Navigating the Jungle Gym of Leadership: Insights from Tiffany To, EVP Atlassian
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This episode features a candid conversation with Tiffany To, Executive Vice President of Atlassian Products and Platforms, about her non-linear career in tech, the evolving landscape for women leaders, and what it really takes to build courageous teams. Shivam and Igor unpack how risk-taking, failure, and experimentation shape meaningful careers, while Tiffany shares specific stories about listening to internal signals, choosing unconventional paths, and leveraging her perspective as a woman in tech to drive change. Together, they explore why psychological safety is the foundation for innovation, how leaders can create “safe-to-fail” environments, and the critical role of mentorship, coaching, and continuous learning in becoming the kind of leader others want to follow.
Sound bites
* "You don't have to conform as much, especially when you’ve earned the right to bet on yourself."
* "You learn so much more about yourself from the risks that don’t work out than from the ones that do."
* "You have to read your internal signals; your body often knows before your brain catches up."
Chapters
00:00 Introduction to Tiffany Ko and Her Journey
01:16 Tiffany's Non-Linear Career Path
07:56 The Evolution of Women in Tech
11:48 Redefining Success: The Pyramid Analogy
18:53 Lessons from Early Career Experiences
22:32 Navigating Systemic Challenges in Technology
23:41 Building New Product Categories
28:15 The Dynamics of Experimentation and Courage
29:41 Creating Psychological Safety for Innovation
36:11 Women in Leadership and Risk-Taking
38:15 Learning from Failures and Personal Growth
40:50 Resources for Personal and Professional Development
Featured Topics & Insights
The Career Pyramid: Why starting broad across regions (like Japan and China) and functions builds the best leadership foundation.
Systems of Work: Moving beyond "raw technology" to help customers realize a clear ROI through AI-powered workflows.
Internal Signals: Why high achievers need to stop focusing solely on "winning" and start listening to what brings them joy.
Leadership Resources: Tiffany’s top picks include Brené Brown’s Dare to Lead and The Knowledge Project podcast.