Ep. 170 - Why the Future of Work Belongs to Multi-Discipline Scalers + How AI Will Reshape the Org Chart

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Guest: Casey Woo, CEO & Founder of Operators Guild & FOG Ventures -- 

What happens when startups are built not by armies of specialists, but by lean teams of senior generalists paired with AI agents? 

In this episode of SaaS Backwards, we sit down with Casey Woo—CEO and Founder of FOG Ventures and the Operators Guild—to explore how AI is transforming the fundamental structure of companies. 

According to Woo, the org chart of the future isn’t just flatter and faster—it’s hybrid, where strategic, multi-discipline humans lead and AI agents handle executional work once done by junior staff.

From finance and support to engineering and ops, AI is hollowing out the middle, forcing leaders to become broader, sharper, and more cross-functional. 

Think “Special Forces” over traditional departments. The operators who thrive will be the ones who can think horizontally, move fast, and execute across domains.

Other key insights from the episode include:

• 🪖 Why early-stage startups need “scalers”—T-shaped operators who do a little of everything—to survive guerrilla warfare, not corporate specialists trained for big wars.
• 💥 The rise of roles like COFO (Chief Operating + Financial Officer) as titles and functions blend in response to new business demands.
• 🚀 A framework for understanding when to bootstrap vs. raise VC—and why many founders get it wrong by ignoring ROI and lifestyle trade-offs.
• 🌍 How Casey accidentally grew the Operators Guild into a 1,200+ member global force, and why its culture of “give more than you get” is key to its explosive success.

If you want to understand what the next wave of high-performance SaaS companies will look like—and who will build them—this conversation is essential.

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