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The Rules of Tech Leadership Have Permanently Changed.

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I'm Mahesh Guruswamy.

In over twenty years I've gone from engineer to COO, across Amazon, Smartsheet, Kickstarter, and Kajabi. I had no formal training for most of it.

I'm Mahesh Guruswamy.

In over twenty years I've gone from engineer to COO, across Amazon, Smartsheet, Kickstarter, and Kajabi. I had no formal training for most of it.

Everything I learned about crossing functional lines at the executive level, I figured out in the field, often by making expensive mistakes. You may not have the luxury of learning it the same way. AI is collapsing functional roles faster than any previous shift in this industry. The leaders who don't get ahead of this transition will be forced into it and not on their terms. 

This course is what I wish had existed. This course is for senior leaders and executives who want to make the transition from functional specialist to General Manager: whether you're a VP, CTO, CPO, CMO, COO, or a CEO who wants a shared framework for how your whole leadership team thinks and operates. 

But because that transition is now urgent, not optional, I'm giving away the first module for free.

Everything I learned about crossing functional lines at the executive level, I figured out in the field, often by making expensive mistakes. You may not have the luxury of learning it the same way. AI is collapsing functional roles faster than any previous shift in this industry. The leaders who don't get ahead of this transition will be forced into it and not on their terms. 

This course is what I wish had existed. This course is for senior leaders and executives who want to make the transition from functional specialist to General Manager: whether you're a VP, CTO, CPO, CMO, COO, or a CEO who wants a shared framework for how your whole leadership team thinks and operates. 

But because that transition is now urgent, not optional, I'm giving away the first module for free.

INSIDE THIS FIRST MODULE, YOU'LL LEARN:

  • Why the tech industry has permanently matured, and what that means for how leaders are evaluated today
  • How twenty-five years of booms, crashes, and free money built the leadership playbook most of you are still running
  • Why that playbook is now working against you
  • What AI and financial discipline arriving at the same moment means for your role and your timeline
  • What the GM mindset actually requires, and how to start building it before anyone asks you to

IF YOU ARE

If you're a senior leader who feels like the ground has shifted and isn't sure your footing is as solid as it used to be, or a CEO watching your leadership team struggle to operate cross-functionally in a moment that demands it, don't miss this free inside look at Rewired for the Future. 

That feeling is right. The ground did shift. And the window to adapt on your own terms is shorter than most people realize.

Inside Module 1: The World Has Changed. Have You?

Inside, I share exactly how we got here and why the skills that made you a great functional leader will cap you as an executive in the new era. By the end of this module, you'll have a clear picture of why the transition to GM is no longer optional, and what your first steps toward making it look like. This includes:

  • The maturation of tech: what it means that the industry is now establishment, not disruptor, and why boards are demanding a rigor most leaders have never had to operate under
  • The ZIRP era playbook: how free money built six specific assumptions into how you lead, and why each of them is now a liability
  • The AI and austerity collision: why this moment is unlike anything that came before it, and what it's compressing faster than you think
  • Why functional titles are collapsing: CTO, CPO, CMO as separate roles is already starting to give way to something else
  • What the new era actually demands and what you need to start building now

Meet Your Host

Mahesh Guruswamy has spent 20+ years navigating the path from software engineer to COO. He's held senior leadership roles at Amazon Alexa, Smartsheet, Fidelity, Vanguard, Kickstarter, and is currently the COO of Kajabi. He's the author of How to Deliver Bad News (Greenleaf, 2025) and writes The Sensible Manager on Substack. He doesn't teach theory. He teaches pattern recognition from twenty years of being in the room, and occasionally being yelled at by everyone in it.

  20+

Years

6

 Companies

Every hard transition made without a roadmap, so you don't have to.

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