SaaS Backwards - Reverse Engineering SaaS Success

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

Jun 27, 2025

Casey Woo, Founder and CEO of the Operators Guild and FOG Ventures, dives into how AI is reshaping organizational structures. He argues that lean teams of multi-discipline scalers, rather than specialists, will thrive in today’s startup world. Learn about the emerging roles like COFO, and why early-stage startups require versatile operators. Casey also discusses the critical decision of whether to bootstrap or seek VC funding, emphasizing lifestyle impacts. Discover how community growth nudges the future of operational roles and collaboration.

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INSIGHT

Scalers Are Early-Stage Force Multipliers

Early-stage startups need multidiscipline "scalers" who bridge finance, ops, and strategy to move fast.
These T-shaped operators are more valuable than heavy specialists during guerrilla-style growth.

ADVICE

Hire Multidiscipline Operators Early

Hire operators who can do multiple roles rather than specialists until you reach scale.
Expect early finance hires to handle HR, contracts, and ad-hoc tasks beyond pure accounting.

INSIGHT

Guerrilla Warfare Beats Big-Force Tactics

Early-stage growth resembles guerrilla warfare where small, horizontal teams win through speed and versatility.
Special Forces-style operators outperform deep specialists in fast, ambiguous fights.

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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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