The Scaler Role, Personality Traits and Business Impact - with Casey Woo, Founder and CEO Operators Guild

**Ray Wright** (0:00)
Hello, I'm Ray Wright, Founder and CEO of BenchMarket, and your host of the Metrics It Measure Up podcast. We talked to a wide variety of the top B2B SaaS and Cloud thought leaders, CEOs, executives, investors, and people just like you to discuss the metrics and benchmarks they use to make metrics informed and benchmark validated decisions. Now, on to today's show. Welcome to today's episode of the Metrics It Measure Up podcast. Today, I am joined by Casey Woo, who's the founder and CEO of the Operators Guild and the general partner at Fog Ventures. Today, we'll be covering three primary topics with Casey. First, the need for scalers, thanks special forces. Second, the scalar personality. And third, a little bit more insight into the Operators Guild. So with that, Casey, can you please take a moment to give a brief overview of your journey to becoming my guest here on the Metrics That Measure Up podcast?

**Casey Woo** (1:09)
Yeah, great to be here. My journey at the highest level is I went to the military, I went to West Point. Then I went to Harvard to finish out undergrad. So I have this kind of like dual type of college experience. That shot me into Wall Street. And we can talk about that a little bit more. But as an economics major, Wall Street was one of the short lists of places you go.
I spent about 10 years in New York doing investment banking and hedge funds during the heyday. And then I realized I wasn't fulfilled, not because it wasn't a great career or job, but there was something missing. That led me to tech. And so the last 12 years, I have been a part of six startups in various roles from COO, CFO, BizOps to founder. And along the way, built the operator community for tech and discovered the missing persona and the missing community, as well as started the number one operator syndicate, Fog. So my entire world is focused on serving the scaler or the operator, and as well as we have a talent agency as well. So all things for the elite tech operator.

**Ray Wright** (2:25)
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Get two months free and 50% off implementation for a limited time for Metrics at Measure Up listeners. That's D-R-I-V-E T-R-A-I-N dot A-I slash metrics. Yeah. Well, we won't be able to cover this today, but sometime over during, I'd love to talk to you about your experience that we work where you were the global head of strategic finance. I'm sure you've got some amazing stories.

**Casey Woo** (3:29)
I definitely do. And West Point. Both are pretty wild.

**Ray Wright** (3:33)
So most people who know me know me, I'm a high energy and kind of a tape eye driver personality. But when I first spoke to you, Casey, I felt like I just had a shot of double espresso and I really loved it. And the topic we were discussing was so not what I thought we'd be talking in was about how businesses like warfare, which I get from your West Point background. And then it quickly moved into the similarities between special forces and special ops and military and what we need in business. So can you share your perspective behind that analogy you shared with me?

**Casey Woo** (4:08)
Yeah, absolutely. So I think in analogies and the analogy that came up after interviewing 1,200 people for my operators group called Operators Guild, I started to realize and it hit me. So the analogy is when you think about war, it used to be big wars, World War I, World War II. The farther back you go, it's just mass, massive type situations. And so you have an army, a navy and an air force. And we look at big anything, corporate. You have specialists. That's how humans are organized. Army is for land, navy is for sea. And it makes sense. Look at corporate. Sales, marketing, legal, product. So you go to Oracle and those are massive departments, as they should be. Why would sales need to sit with accounting? They don't. So when it's big warfare, big corporate, that makes sense. And for the longest time, that's what business was, was big corporate.