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Your functional title is about to expire. Most leaders aren't ready.

AI and financial discipline have arrived at the same moment. The functional leadership playbook most senior leaders are still running was built for a different era. It's now working against them. The transition to General Manager is no longer a career option. It's a deadline.

Get Free Access To Module 1
No credit card. No catch. One module, free.
The window to make this transition on your own terms is shorter than most people realize.
 

"The leaders who don't get ahead of this transition will be forced into it, not on their terms."

MAHESH GURUSWAMY, COO, KAJABI

Your functional title is about to expire. Most leaders aren't ready.

AI and financial discipline have arrived at the same moment. The functional leadership playbook most senior leaders are still running was built for a different era. It's now working against them. The transition to General Manager is no longer a career option. It's a deadline.

Get Free Access To Module 1
No credit card. No catch. One module, free.
The window to make this transition on your own terms is shorter than most people realize.
 

"The leaders who don't get ahead of this transition will be forced into it, not on their terms."

MAHESH GURUSWAMY, COO, KAJABI

This is for senior leaders who feel like the ground has shifted.

If you've built your career as a functional specialist — the best product person, the best engineer, the best marketer — that skillset got you here. But the skills that made you exceptional in your function are now actively capping you at the executive level.

This course is the transition framework for VPs, CTOs, CPOs, CMOs, COOs, and Senior Directors who want to make the move before someone makes it for them. And for CEOs who need their entire leadership team to stop operating like specialists and start operating like a business.

This is for senior leaders who feel like the ground has shifted.

If you've built your career as a functional specialist — the best product person, the best engineer, the best marketer — that skillset got you here. But the skills that made you exceptional in your function are now actively capping you at the executive level.

This course is the transition framework for VPs, CTOs, CPOs, CMOs, COOs, and Senior Directors who want to make the move before someone makes it for them. And for CEOs who need their entire leadership team to stop operating like specialists and start operating like a business.

The era of the specialist leader is ending.

 

For twenty-five years, cheap capital rewarded depth over breadth. Companies hired specialists to own their function, and the org chart kept everyone cleanly separated. That model produced enormous value, and deeply ingrained habits that are hard to shed.

Then ZIRP ended. AI arrived. And the assumptions baked into how most senior leaders operate stopped being competitive advantages and became liabilities.

The board now wants GMs. The business now requires cross-functional fluency. And the window to make that transition on your own terms is shorter than most people realize.

What changed, and when

01

The ZIRP era built six assumptions into how you lead.

Free money rewarded growth over discipline, specialization over integration, and headcount over leverage. Each of those assumptions is now a liability.

02

Tech matured from disruptor to establishment.

Boards are demanding operational rigor most leaders have never had to operate under. The startup playbook stopped working when tech stopped being a startup.

03

AI is collapsing functional titles faster than anything before it.

CTO, CPO, and CMO as cleanly separate roles is already giving way. The executives who adapt are building a new kind of fluency. Everyone else is waiting.

The era of the specialist leader is ending.

 

For twenty-five years, cheap capital rewarded depth over breadth. Companies hired specialists to own their function, and the org chart kept everyone cleanly separated. That model produced enormous value, and deeply ingrained habits that are hard to shed.

Then ZIRP ended. AI arrived. And the assumptions baked into how most senior leaders operate stopped being competitive advantages and became liabilities.

The board now wants GMs. The business now requires cross-functional fluency. And the window to make that transition on your own terms is shorter than most people realize.

What changed, and when

01

The ZIRP era built six assumptions into how you lead.

Free money rewarded growth over discipline, specialization over integration, and headcount over leverage. Each of those assumptions is now a liability.

02

Tech matured from disruptor to establishment.

Boards are demanding operational rigor most leaders have never had to operate under. The startup playbook stopped working when tech stopped being a startup.

03

AI is collapsing functional titles faster than anything before it.

CTO, CPO, and CMO as cleanly separate roles is already giving way. The executives who adapt are building a new kind of fluency. Everyone else is waiting.

MODULE 1 — FREE

The World Has Changed.

Have You?

 

Everything you need to understand why the transition to GM is no longer optional, and what your first moves look like.

  • Why the playbook that got you here is now the thing most likely to cap you

    Twenty-five years of booms, crashes, and free money — and the leadership playbook it produced. Understanding the era explains why the playbook made sense then and why it's breaking now.

  • The six ZIRP-era assumptions, and why each is now a liability

    Specific, named assumptions that were built into how most senior leaders operate. You'll recognize all six. At least three will feel personal.

  • Why the org structure you're operating inside right now is already being redesigned around you

    AI and financial discipline arriving simultaneously isn't additive. It's compressive. The timeline for adapting is materially shorter than most leaders assume.

  • What the GM mindset actually requires

    Not a job title. A way of operating. The first concrete look at what cross-functional executive fluency means in practice, and how to start building it.

Twenty years of expensive mistakes, so you don't have to make them.

 

I spent two decades going from software engineer to COO, across companies at every stage and scale. I'm currently the COO of Kajabi. Previously: Amazon Alexa, Smartsheet, Kickstarter, Fidelity, Vanguard.

I had no formal training for most of the transition. Everything in this course I learned in the field, by being in the room when hard decisions got made, and occasionally by being wrong about them.

I'm also the author of How to Deliver Bad News (Greenleaf, 2025) and write The Sensible Manager on Substack.

I don't teach theory. I teach pattern recognition.

 

20+

YEARS NAVIGATING THE TRANSITION

 

 

6

COMPANIES ACROSS EVERY SCALE

 

 

1

PUBLISHED BOOK (GREENLEAF, 2025)

Twenty years of expensive mistakes, so you don't have to make them.

 

I spent two decades going from software engineer to COO, across companies at every stage and scale. I'm currently the COO of Kajabi. Previously: Amazon Alexa, Smartsheet, Kickstarter, Fidelity, Vanguard.

I had no formal training for most of the transition. Everything in this course I learned in the field, by being in the room when hard decisions got made, and occasionally by being wrong about them.

I'm also the author of How to Deliver Bad News (Greenleaf, 2025) and write The Sensible Manager on Substack.

I don't teach theory. I teach pattern recognition.

 

20+

YEARS NAVIGATING THE TRANSITION

 

 

6

COMPANIES ACROSS EVERY SCALE

 

 

1

PUBLISHED BOOK (GREENLEAF, 2025)

Start the transition on your terms.

 

Get free access to Module 1 of Rewired for the Future. No credit card. No commitment. Just the clearest picture you'll find of what the shift demands, and what to do about it.

 

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