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

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.

---

Not Getting Enough Demos?

Your messaging could be turning buyers away before you even get a chance to pitch.

🔗 Get a Free Messaging & Conversion Review

We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations.

And the best part?

💡 It’s completely free.

No commitments, no pressure—just actionable advice to help you book more demos.

Your next demo is just a click away—claim your free review now.

Transcript

Welcome to SaaS backwards, a podcast that helps SaaS Founders, CEOs, and go-to market teams to accelerate revenue and increase profitability. Our guest today is Casey Woo, CEO and founder of the Operators Guild. An independent and invitation only group that's home to the world's top operators in tech.

Ken Lempit: He's also CEO and Founder of Fog Ventures, a VC firm that was created to invest and support innovative Founders that are helping create the toolbox 2.0 for the modern day operator. And lastly, he's also in the process of writing a book about a distinct class of executives. He's dubbed as Scalers welcome to the podcast, Casey.

How are you?

Casey Woo: I'm good, thanks for having me, Ken.

Ken Lempit: Excited to dig in on great conversation. But before we do so, could you please tell our listeners a little bit more about yourself and these two companies?

Casey Woo: So I run the Operators Guild, which is now a close to 1200 person, global organization of some of the best tech operators in the world. The easiest way to call say it, is we don't code or we don't sell. So there are those who build it at a company, product engineering, those who sell, sales and marketing.

And in my opinion, there's a third class that used to be considered a, a back office cost center. They were called accountants and the finance people. And the operations people. And now I call them the scaler. So those who build, sell, and scale. We are the scaling organization. A lot of the famous probably names of tech companies you'll know of, we consider our members.

You go on the website and you can see more of them. But the titles are CFO, COO, early Stage Founder, BizOps, Chief of Staff, General Manager, Rev Ops and Director and above for all those categories. And then we do 150 events a year around the world. More importantly, I think we build incredible friendships.

We understand each other and we solve all the scaling problems together. Through online and offline. And then FOG Ventures stands for For Operators Guild. It is the investing arm syndicate of Operators Guild. We have considered some of the best tech deals in the world. If you heard some of the deals, you'll know exactly who they are.

We're stage agnostic from pre-seed all the way through pre IPO. We have a lot of fun investing in deals together as not only the buyers, but builders of a lot of these companies. And so, yeah, that's a little bit of what I do. Oh, and then of course, all this was inspired, a, a book I'm writing. The working title is the Scaler the Rise of Special Forces in Business, which is essentially startups used to become a hobby in terms of joining one and helping to build it is now a profession.

I've spoken to over 1200 operators. It occurred to me this is now a, a formal persona and career path to do early stage hypergrowth. And I call it the scaler.

Ken Lempit: I think that's a really, I mean there's a valuable insight and the only time I've heard it kind of collected this way, we, we've talked about the importance of the sales and marketing leaders, the GTM leaders to collaborate plan with. And execute alongside like the CFO people. But I think this is the first time on the podcast for sure that we're gonna explore this topic, and I think it's really important for Founders who may not have all the skills needed to scale up their organization, to surround themselves with solid operating talent.

So I think this is a great topic for our audience. and why don't we, why don't we explore this emerging professional category. Now, the, the idea of a scaler is the emerging idea here. These folks exist in many organizations. Perhaps the CFO comes too early or too late. How did these multidisciplinary professionals differ?

From more traditional specialists. And why is it crucial to staff this early in the life of a, of a SaaS organization?

Casey Woo: I ended up having to decide to write a book on it to answer it thoroughly. So I'll try my best to answer it in, you know, three minutes. But basically to me everything's on a spectrum. So when you think about stage of company from one person to Walmart, the later a company in general, the bigger and more corporate a company, the more you specialize.

You know, for example, I bet you IBM has a hundred people that just do payroll because they're big. Now imagine the extreme. You're two people, a dog and an idea. There is no money yet. There is no specialist yet. What do you mean you do everything? The dog does everything. That's what it's like. So if you believe that framework, early stage tech.

We're talking sub 50 people to start, you know, sub 30, sub 20, sub 10, sub 5. Oh, and also you're against the clock. So the other thing about early stage tech, so specifically I talk about fast moving more,

I would call sophisticated type of early stage. So not to pick on a pizza shop or a cupcake shop, but generally speaking they're not moving really quickly or super complex.

So it's fine to have a, you don't need too many sophisticated generalists, but at early stage tech you do. In fact, if there's Founders listening, which I'm sure they are, most Founders that are very good are multi-discipline. They're trying to arrange an office lease on one side. They gotta hire an accountant on the other side.

They gotta fundraise or they see they gotta go sell four deals. They gotta deal with the marketing funnel. They gotta hire their CMO. That is as multi-discipline as it gets. So right there, the value of a multi generalist, I hope is obvious. Is at early stage, it is hyper valuable. At later and later stage, it is less valuable.

Not to say it's not valuable, but it doesn't apply as much because you're so big. Another reason of the the ailment of the big companies, right, is they can't move as fast, right? But they're cash flowing and it's more on optimization game. At later companies you do have multi generalists. I, for example, Google X or Amazon has a, it's kind of a startup division.

Yeah, you need to separate them from the big company and let them be free to try different things and experiment and innovate. And so that's really, really important to have a more of a generalist nature.

Ken Lempit: I think it would be good to maybe talk about like the third person, right? So you have the two Co-founders and

Casey Woo: Yeah, yeah, yeah, yeah, yeah, yeah.

Ken Lempit: so these guys are often splitting two important domains. They're building and selling. So this next person

Casey Woo: yep.

Ken Lempit: could be that, you know, that more general, multidisciplinary person, and I don't think that Founders think that way necessarily.

So I think that might be a good place to just dig in a little.

Casey Woo: You know, everything evolves, you know, so there's no black and white. But you know, in the beginning I'm gonna make it up. You know, there's a founder who doesn't wanna be in the financial model, but kind of has to do some financial modeling. Okay? And so what happens is they generally hire for things they don't like.

Or they're not good at, or they need more of. Right? So, you know, if you're more of a visionary founder, you'll hire an operator or finance person to start handling the model and finance, right? And so over time the, you know, employees 3 through 50, some will be specialists. Like you need a marketing person, right?

Or you, you know. But a lot of them actually need to serve more than one role. So it's very rare that if you get a director of finance or someone that I think it's relatively sophisticated finance that they only do finance. If you're an early stage head of finance, you're doing HR, you might be playing lawyer for NDAs, you start to do a lot of these things that you don't have the money for or is not gonna justify a general counsel, or you're not gonna justify a senior accounting manager.

You know, we just kind of do it ourselves, right? Or you outsource it. So the beginnings are very fractionally and you need a little bit, you don't need a lot. Just to move things along. So from employee 3 to 50, you start to have what I would call scalers or generalists. Now they do have titles. Their titles are generally not generalist.

They come in the form of finance and operations. I think if you're starting about sales and marketing, I consider that selling. I don't consider that scaling even though it's a different type. But basically the way to think about it is there's vertical and horizontal. A vertical specialist I think is like engineering.

Sales. You know, even, you know, legal, the analogy I use just bear with me, is the military. Army, Navy Air Force. They're specialists, they're deep specialist function, Land, Sea and Air. Sales, Engineering, Legal. It makes sense. So it's pretty clear in the Army you do tanks and infantry, you don't do fly, right? And it's very clear, so, so there's a lot of clarity and specialty because you have to run all the tanks or you have to fly all this and they're totally different.

Sales and Legal, totally different. And then they interact. Okay? However, in war there's big wars where you have the big branches. But all of a sudden, 70 years ago, thereabouts, special forces was created. Why? Why do you need Navy SEAL's? Why do you need Green Berets? Why do you need Delta force? What? You have an army, literally.

And the reason why, in my opinion is wars got smaller. So gorilla warfare you know, Vietnam War, right? Things where you could not just drive tanks and it's all, you know, it's very precision. Small, moving high, fast, but still sophisticated Special forces people are some of the best. Of the Army, Navy Air Force, okay. So this is not just, but if you actually kind of look at how they're organized, they're horizontal. So a Navy SEAL knows that needs how to swim, run, fight, teach, shoot, save, because there's only 10 of 'em on a mission. They can't bring the whole entire, you know, doctor force and all. No. They gotta like, you know, someone's gotta fly the helicopter and then repel out of it and then, you know, so.

That's the exact analogy in business. Early stage hypergrowth is gorilla warfare. So the people you need to air quote, fight the battle or the business and business is war. It's just not violent, right? It's taking share, right? Resources, running out of it, supplying up. You have competitors, right? You're taking land, which is basically market share.

The soldiers you need the better they are as generalists. Probably the better you can succeed to scale quickly and to maneuver until you become a bigger war like Amazon. Then you have big specialist teams. So that's the analogy I use for people that are Founders, et cetera, is every business is different.

But if you have someone that is more of a special forces personality, which is basically the get it done. They're a little bit deadly at everything. Or I call T Shape. They understand the overall business, but some spike in finance, some spike in systems, some spike in people. You gotta mix those together.

And the book talks about the different types of scalers. They are who you really need to fight the small war that you start with. But if you bring in specialists, heavy specialists to a gorilla warfare, it doesn't really work. So, so the example would be the, you know, the big shot at Google who's used to size.

Imagine bringing them into a 10 person company. Of course they're smart, of course they're good, but it's a different type of fight. So that, that's what I'm trying to say. And we can get out of analogies and go into any more specific, but there's the accountant, so to speak, and then there's the strategic CFO.

and that's the difference.

Ken Lempit: Yeah, it makes a lot of sense. you know, We've seen mismatch. You know, when people hire, like, like your example, you know, a Google person into a startup. If they didn't come from that startup world, they may not know it. You know, in our business it's very hard to take a nonprofit marketing person and make them a great agency exec.

Just, it's just such a different clock that they operate on.

Casey Woo: That's exactly right. There's a speed. There is a comfort with ambiguity, and I can go into that more, but there's a persona, there's an actual persona that lends itself better or worse to earlier, later stage.

Ken Lempit: I, I wanna kind of flip this around a little bit and, and talk about investability of these young companies, right? Because these companies are getting smaller, not larger, right? The, the AI impact on a lot of these young companies is that they are smaller. So how does this impact their ability to staff and attract investment capital?

And, and also I, I didn't put this in the prep for you, but I wanna talk a little bit about the bootstrap mindset. I've run into a few of these AI first, you know, AI, native application Founders, and they're almost spurning investment and I, I think it's such a mistake, you know, especially they, like, I've met one recently and they said, well, I'd like to sell between 12 and 18 months.

And, you know, he is trying to bootstrap his way to a saleable business and I feel like they don't, maybe some of these Founders don't understand. The math of growing a business for sale, scaling for sale, and they, they're like, Hey, I'm profitable at two and a half million in ARR. Why should I take investment money and dilute myself?

And it's hard to explain to them that you might get four times as much money if you took investment and really scale.

Casey Woo: I love this topic. It's a very good one. I'll first tackle it in different, different lenses. I've been at WeWork, which is the ultimate go for go crazy. And I run my own, what I would call bootstrapped businesses. So I've kind of done the, again, I've, I've done five or six different startups from series A paper.

So what I've learned is one question a founder has to ask themselves is lifestyle. Yeah, before you take money, it's not it, I don't, I don't think it's a spectrum on that sense. Once you take money, it's a step function difference. It's not a little bit different. Meaning, and I, I use extremes again, if you don't take money and you bootstrap it, one of the things that generally happens is you have a lot of control.

And let's say you're cashflow positive, there's a lot more patience. There's a lot more answering to no one. And for someone that, you know, I have a friend who likes to spend time with his kids and do what he wants, but he makes far less. That is one reason why I think if your business could get bigger, you don't. If you take money, and I remember this meeting with a, a young founder. I was this, I was the CFO and I was first startup.

He goes, are you sure you wanna take my check? He is like, well, why? He said, yeah, I do. You can take it. And when you take it, the goals we're gonna get, you're gonna be a lot richer and we're gonna be much bigger, which I think this business can. But it's not gonna be this lifestyle business you have right now.

You are gonna need to triple sales, right? You're taking the money. So when you take money, there is an obligation to grow because generally, generally you're raising money at a higher valuation. All valuation is that's higher, is baking in some sort of growth assumption, profit assumption, growth assumption.

So once you take money, the deal is I will give you more resources, but the war just got bigger. You need to capture more treasure and more land and, and so meaning, part of it people forget is not just that, can I get rich question? Do I wanna fight that war? Do I wanna wake up every day and fight a bigger war?

Some people do, some people don't. Okay. That's the lifestyle. The the other side is there are businesses that should take money from a pure, just ROI is what I call it. Like this business could be 10 times bigger. You know, and the return on money is well worth, you know, more than 20% a year, then you do it.

This is not an emotional question. This is a business opportunity, opportunity cost question. And dilution is just one of the formulas in the total thing called shareholder value. I mean, we all know Bezos doesn't own a hundred percent Amazon. He got diluted a lot. I think he's also one of the richest people in the world.

So I don't need to give that explanation to people, but. Smaller slice, bigger pie. But to me the real difference is not, okay, do I want a bigger pie or not? It's one, can my business be a bigger pie in terms of the, you know, $1 in $4 out? Some businesses are $5 in $2 out. Yeah, that's not gonna work. And then the other is it could be a bigger business and a good ROI, but I don't want to do it because the other thing people forget about is their time.

Their life and their time so they can spend their time hustling more, which is fine, and make more money, which a lot of people chose or something else. Right? So anyways, those are the factors. Do you factor that in? Yes. A lot of companies, I think a lot of Founders can get a lot bigger. There are some that don't think they can get a lot bigger.

Ken Lempit: they might limit themselves,

Casey Woo: Yeah. So, so, so, so they're, they're, they're happy to go hard and to, you know, scale up. They don't know how to or who, and that's the whole scaler thing. You have a strategic CFO or strategic COO, they can very much paint a picture for you and help you fundraise, but not just fundraise.

What are the use of proceeds to start to model out scenarios? If we got an extra million, what we do with it? How do we test small and know that this might work before we, you know, we put the whole million in. So there's quick testing, quick iteration is another way to do it. But yes, in general, things are moving smaller because you can do a lot more with less 'cause the power of technology, AI, etc

Ken Lempit: Yeah, I, I guess I also feel like the missing thing in that conversation was that the moat is so different now, right? So the moat now is execution. The moat isn't, you have a great idea or you code well, right? The moat is really, are you gonna. Be better at growing the business than your competitors.

Casey Woo: I think if you double click into that, it's, it's more than execution. I think right now it's brand and distribution, because what's happening is everyone's got a solution to a problem. There's so many solutions to your problem and they can get created so fast. To your point about no moat, the only person that's gonna really win in theory, it's whoever can have a brand or a distribution vehicle, translation, sales that's gonna monetize.

That's why there's a whole question of like Granola. I, I love the product. I dunno if you know it, it's a transcribing device. They had a genius idea to record and subscribe, but never record digitally. It's always, it's, it's just written down and it kind of changed the game a bit on note taking as compared to what Otter's doing, which is, it records everything.

Well Chat GPT just did the same thing. No moat. We'll transcribe without recording. I dunno who's the winner. Maybe the person with distribution

Chat GPT has a hundred million users, so their distribution power allows 'em to monetize. So TLDR who can monetize, not even execute. I can execute on a product, I can execute, I can build whatever you want.

If I'm not getting customers to pull out their credit card. It doesn't matter. The other one is velocity. So distribution and velocity. I think Mark Zuckerberg said it. He goes, look, I don't know if we're going in the right direction, but we're gonna win because my team moves faster than any other team. The min, because there's no moat, right? So, oh, we're wrong. Turn on a dime. Sorry. Take your better idea. Let's go. Right. So velocity. Everyone's got an idea, to your point, so everyone can build a product. Technology no longer is as much of a differentiator. And then there's brand, right? The, the Hermas of the world, the, you know, CHat GPT is a trusted brand, right?

You build whatever Harvey AI for Legal, there's other legal things, but you know, for some reason, I feel like Harvey's the leader. So, yeah. So I agree with you, but I think it's moving toward, oh, and it's moving toward multi, multi-discipline generalists. 

Ken Lempit: I think we should talk about the impact of AI on, the staffing, the people doing the work. You know, how, how is it changing the roles of these leaders and, what should the C-suite be aware of and how, how are they gonna manage to that?

Casey Woo: Ai basically, to me, in this current stage, it's doing two things. One is it's substantially impacting things like junior copywriters, potentially bookkeeping and customer support like, like truly starting to take a big dent out of it. And the org chart of a support team will start to look like a senior, some senior generalists.

At the top and AI agents, right? It's the Human plus AI agent combo. And I think that's gonna continue to happen across finance, et cetera. It just, some, some functions will take longer to crack like finance because it's more complicated as money implications. It's not as easy as customer support, you know, FAQs and things like that.

Okay. I think it's an inevitable world of a hybrid org chart of, when I say senior, I mean people that are multi-disciplined and agents because what's gonna happen is the need is horizontal. So AI agents are taking care of specialty things. Writing emails, you know, whatever the interns, you know, are doing, so to speak.

The more specialized, I think the more programmable it's anything horizontal is more complicated strategy, more complicated because it takes in multiple things, including personal relationships. You know, there's a whole bunch of things that are not as structured as, you know, writing a, an article. So that's gonna continue to move where, you know, I think one idea is in the RnD department.

Engineers that have ideas or basically product people are gonna be the people left. 'cause if in theory, if you're an engineer that just codes, it's like purely just codes, right? In theory, you need less of them. But the engineer who has an idea, who has product chops, they can use the AI agent to code, but then adjust the product, right?

Because they're more than one. The minute you're more than one something. So finance, same thing. CFOs are gonna become more strategic. They're business people who know finance. If you're just purely a finance person trying to model, there's AI that will just model for you. They'll give you scenarios, right?

But you need someone who has way more than just finance forecasting abilities. 

Ken Lempit: It's really interesting, you know, I was thinking as, as you're speaking, that's advice I got in 1978 from my department head in the MIS group at Syracuse. He said, you can't just be a programmer. Go get another degree while you're here. So I ended up with a marketing degree 'cause he said one day you might be career limited if you're just a programmer.

It didn't happen as quick as you might've imagined, but I think it is here today.

Casey Woo: incredible insight. 'cause I think that was a huge surprise. And I said, you know, when did we ever think an oil painter degree might be worth more than a computer programming degree? Like when, when did we ever think that was gonna happen? And yeah.

Ken Lempit: Yeah, those folks are facing a little bit of decline in demand at the moment anyway. But let's move on a little bit, but sort of similar kind of topic area. We, we sort of said, Hey, if you're at Google, maybe you're not a great fit for startup, but let's say that's really what you wanna do. What, what can this person that's in a traditional corporate organization, how can they get themselves into the startup environment?

Like what should they be? What skills should they be building or highlighting to get the attention of these very early stage companies?

Casey Woo: Well, I think it very much depends on the role. But I do think in general you need to be able to prove the hustle. I think the stereotype of large corporate is used to a lot of resources, not used to breaking things and moving fast as much. what I would do if I was late stages, I bring all the best practices of a Google, of a, you know, great company. But I'm yearning to get back in there into an early stage where I can move faster, innovate, make bigger impact as, as one person rather than, you know, 10,000 person.

But move us toward best practice, right? So acknowledging that different stages have different best practice. The best practices at Google right now are, do not work for a series A company, right? So number one is understanding that, expressing that, but also showing this, I'm gonna bring this maturity and best practice future growth, but I wanna operate and can operate in a more scrappy, innovative.

Environment and then I'm gonna bridge it. I'm gonna bring us there. Right? So, so that's a big one.

And the other one is, prove to me you understand the dysfunctions and crazy of early stage anything. You know, it's like, oh yeah, I know what it's like to have kids, you know, it's crazy.

Do you have kids? No. Never. Never had kids. So how do you know? Well, I watch a lot of movies. Well, okay, well. Maybe, maybe you're gonna be cool and maybe you're gonna freak out and be the last Google guy who was like, screw this. I'm going back to Google. Right. So there's definitely just a completely different environment. Goes back to guerrilla warfare versus big war, right?

Very, very different environments. So you gotta prove to them that your yearning and can succeed at early, which is basically multi, multi-discipline, right? So don't be the specialist unless that's literally the job you're applying for is, you know, be the best at left eye surgeon. Okay, fine then, then, you know, prove to them that.

But you need to prove that you are a multi capable business exec that's gonna help the team left and right, not just up and down.

Ken Lempit: Fair enough.

Casey Woo: Oh, last thing. You're not an Empire Builder. Big one. So when they ask you, how many people do you need, like, okay, you're the head of a new department. Great. Give me your vision of, of your next three years.

That is a test. If you come back with a massive org chart and a whole bunch of resources you need, in general, I think that's a bad sign. For an early stage company, they're gonna be like, I, I needed more efficiency and more scrappiness. We can always push the gas easier, but it's really hard to take you back.

So I need to see you as a scrappy, highly efficient and smart. Taking bets when you need to. Not, I need to tell you to cut your budget half the time and do less with more.

Ken Lempit: Fair enough. I wanna, I wanna take some of the remaining time talk about the Operator's Guild. I'd love you to explain that a little more. You know the purpose of the operator's Guild, you know who, who it's for, and then talk to me about how you grew this thing so big. It's a great accomplishment.

Casey Woo: it's a really fun story and accident. I first 10 years of my life was military and investment banking, wall Street. So hedge funds. So I did the, the classic path of, okay I went to Harvard for economics and to West Point before that. And I said, okay, you know, this, this whole Wall Street thing looks awesome and it is. Either that or go to McKinsey, right?

Management Consulting or Wall Street. Okay, great. So I did the investment banking thing. It was great. Learned a lot. Half my groomsmen are from that class. And then I did hedge funds. Also a great profession. But I had a nice, you know, big office overlooking Central Park. I remember my office being bigger than my apartment, I got paid very well.

I got to be an investor. I got to invest and talk to the CEO of Abercrombie & Fitch, and it was awesome. And eventually I got bored. Not because the profession's easy, but just something about it was like not fulfilling me. And so I left and I joined a 10 person FinTech startup in New York. And I loved it. I loved it so much that I was like, why do I like eating glass?

But I had to move to Silicon Valley because at the time, 2010, 11, 12, tech was still Bay Area. And to be taken seriously, it was like, you gotta go to the Bay Area. Okay. So I'm no longer investing Investing, which is New York. I'm doing finance stuff at a tech company. A little company I will not name but is probably one of the most successful FinTech companies in the world was interviewing.

They had 60 people and now they think they're worth a hundred billion dollars by the way, as, and they looked at my resume when I was interviewing and they said, do you code or do you sell? And I'm like I dunno if that's a trick question, but I do finance ops and I clean toilets and I will work for free.

They said, you don't even have a CPA, so how do you qualify for finance here? I'm like, what? There, there's, there's also, you know, strategic finances. This is like 2013. Long story short, I did not get the job. Probably wouldn't be talking to you right now if I did. But instead I got lonely and I'm a flaming extrovert.

Like I love connecting and being with people and so I try to join a CFO group. No offense, it was kinda like Dilbert. I tried to join a founder group, good looking people, great storytellers. A lot of them were smooshing with VCs a lot 'cause they had to fundraise all the time, so they're kind of away from the action.

Okay. I also didn't feel exactly like my people. And then there's nine people. I got invited to a lunch with. Ex McKinsey, ex Goldman, Finance, BizOps, and I was like, you're my people. Hey, do you guys wanna start a little group, like a therapy groups support group? We meet at once a month. There's a few rules.

The rules are give more than you get. Leave your ego at the door. No bullshit, no promotion or solicitation. Do not sell your own book. Safe space. What's said here, stays here. And the last one is relevance. Active operators only, not investors. Not, you know. We called it Bay Area operators. I'm gonna fast forward 10.2 years.

We are the only paid professional organization that I'm aware of that has 100X'd organically. We don't have a sales team. We don't have a marketing team. Everything was word of mouth inbound. So we truly built a community like how friends are built, right? You get to make friends through friends. It's, it's no different.

But it told me something. Why in the world would an organization, it's paid by the way, it is free, then you can grow it as however much you want. But pay means people have to decide. I realized there was a missing community. There's a missing persona. And part of that was because scaling is a new thing.

So before tech put in a trillion dollars in the last 30 years into early stage. Being an early stage hypergrowth sophisticated business person did not exist. You know what existed? Computer Engineering, Product Sales, Accountants, HR, Legal. But this concept of a scaler or special forces Navy SEALs, just like in the military, did not exist until.

There was a fertile ground to support them and that fertile ground is tech. So OG is not nine people, we just crossed 1100 moving to 1200. We're not one chapter called San Francisco. We are 20 chapters around the world including Vancouver, London, Mexico City, Austin, Denver, Toronto. You name the tech code.

You know the biggest ones are New York, SF, LA. And instead of, you know, my sixth startup at that point did five more as CFO, COO, Janitor, BizOps, Interim CEO, and now Founder. It got so big that I never returned back to a operating job. What I operate now is the Operator's Guild. We specialize in all the problem solving.

Whether it's virtual events online, the most incredible answers you'll see to all the problems. Because we're so diverse. Yeah.

Ken Lempit: Do, do you think that there's gonna be a kind of shuffling of the deck of these operational roles and titles? You know, like we in go to market, you know, we have the rise of the CRO, you know, a role that didn't exist in reality five years ago. There were very few people carrying that title. You know, is there some elevation of these operational talents?

Casey Woo: I love that. I love that question. I think the answer is yes. It is gonna be a little, for example, have you heard of COFO? That just got created? COFO? It's a mix between COO and CFO and I believe Salesforce has it. Salesforce has an officer called COFO and I smiled 'cause after 10 years I go, here it is finally. Because CFO, COO BizOps Chief of Staff, it, it's all a get a done job.

Now obviously finance has a finance element, but it really is one minus. So other titles, I dunno, Chief Business Intelligence Officer, Chief Intelligence Officer, Chief Data Officer, which it does exist, but I think more so in the engineering world, I think CFOs and COOs are gonna become Chief Data Officers.

The difference between I think a Chief Data Officer in the more technical world versus the non-technical is finance. Is all the money that runs through the business. And at the end of the day, what is a business it, it makes money. Like, it's the blood flow of a business. So I think it'll move toward the money central figures.

CFO, COO, CEO. But yes, I think that there will be some elevation of title at the same time. Look, titles are important, right? You know, BizOps is gonna get more and more formalized. A Revops. But CRO to me is a nod to finance. 'cause what is R it's revenue. Revenue is actual finance figure. Bookings and Sales is a sales figure.

So the minute you said CRO, it means you care about finance and the business as compared to, I just need to land and book deals. I don't care what the profit is or whatever, you know, like old school just land in deals, right? And then we'll let finance do the pricing. We'll let, we'll let them fix it. But I, I just need to, all I care about is bookings, so to speak.

Nope. Now you care about churn, you care about margin. Oh, that's all CFO stuff. So the world is moving to the center and there will be a probably some new title. Oh, Chief, I mean the Chief AI Officer, right? Things like that's gonna happen. But yeah, it's a, it's a good insight 'cause I think it is gonna come.

Ken Lempit: So I, I think this is a conversation we could have for the whole afternoon, but we have to land the episode somewhere, so I'm gonna land it here. How can people learn more about

The Operator's Guild and Fog Ventures and get in touch with learn more. 

Casey Woo: yeah, go to the website

operators-guild.com

Fog is fog.ventures. Oh, fog by the way, is, you know, is an incredible group. If you love to Angel invest. We talk about deals together, we see Founders, they get to pitch directly, you get to see about the latest products. So yeah, you just go to the websites apply.

Obviously if you qualify, which is basically badass operators. We'd love to have you. Or if you have any questions, you know, you can hit me up on LinkedIn, et cetera. My professional mission is to help people who do this profession. I empathize greatly with Founders, with Scalers and if I can help you in any way, whether that's jobs also, also we have Gild Talent, so we do, the third thing I am a part of is actually Gild Talent, which is basically an executive search agency and talent operation for Scalers.

So for all the CFO's, COOs, General Managers, we are the best at it. So whether it's hiring jobs, investing, therapy events, or problem solving, I got you.

Ken Lempit: That's awesome. Thanks for that. If people wanna reach me, I'm on

linkedin/in/kenlempit

My advertising and demand generation agency for SaaS is Austin Lawrence. We're at 

austinlawrence.com

and if you haven't subscribed to the podcast yet, this is your big opportunity. Go to wherever podcasts are distributed.

Find SaaS backwards and hit the subscribe button and please give us ratings if that directory has that opportunity. thanks so much for being on SaaS backwards.

Casey Woo: Thanks for having me, Ken.