ClickUp’s $1M Bet on the 100× Marketer

By Dan Sanchez · Episode published July 24, 2026

ClickUp’s 100X marketer role sounds bold, but it exposes a bigger question: how should marketers use AI without becoming bottlenecks, losing judgment, or chasing productivity theater?

When I first saw ClickUp’s job posting for a “100x marketer,” I assumed it was a prank or a clever PR stunt.

The role promised one person who could own brand, positioning, campaigns, creative direction, social, content, email, lifecycle marketing, production systems, and quality control. The person wouldn’t manage a team of 50. They’d build the systems, direct the AI agents, and review everything with enough taste to separate great work from garbage.

The compensation came with a million-dollar growth path—not necessarily a million-dollar salary on day one.

It’s a bold bet. It’s also a useful thought experiment because it asks where marketing is going, what AI can realistically handle, and what still requires a human being in the driver’s seat.

My conclusion is simple: a 100x marketer probably won’t replace a marketing team of 50 anytime soon. But a marketer who uses AI to remove organizational bottlenecks can create far more leverage than one who merely produces more content.

That distinction matters.

The 100x marketer sounds impressive—but the job description hides a problem

ClickUp’s definition of an “artisan” is compelling. This person has refined taste, understands the audience and market, knows what to build, and can evaluate dozens of AI-generated options quickly. The agents are the hands. The marketer is the taste and judgment.

That’s a much better description of advanced AI-assisted marketing than “just write better prompts.” The real work involves orchestrating systems, evaluating output, correcting course, and making high-stakes decisions without endless committees.

But the description also quietly bundles together several highly specialized jobs.

Brand strategy and positioning
Campaign strategy
Copywriting and creative direction
Video and visual production
Social media and community engagement
Email and lifecycle marketing
Marketing operations and automation
Quality assurance across every channel

It’s possible to find people who are strong in several of these areas. It’s extremely rare to find someone who is elite at all of them, understands AI systems deeply, and can operate inside a large company without becoming overwhelmed by meetings, approvals, politics, and competing priorities.

Even if that person exists, why would they take the job?

Someone capable of building and running a 100x marketing operation may already have a profitable consultancy, agency, product, or small company. They may value control and flexibility more than a large compensation package tied to someone else’s strategy. A million-dollar opportunity will attract applicants, but it won’t necessarily attract the one person who can actually do everything the role demands.

AI agents require tradeoffs, not just more capability

One reason this role feels premature is that people often discuss AI agents as if more capability automatically solves the problem.

It doesn’t. Every system has tradeoffs. An agent may be fast, tireless, and capable of producing dozens of variations. But it may also lack context, taste, accountability, or the ability to recognize when a technically correct output feels completely wrong for the brand.

That last part is especially important in marketing.

I can get away with AI-generated thumbnails for an AI marketing show because the audience expects that aesthetic. But other brands I work with can’t use the same approach without seeming inauthentic. Their appeal depends on a more human point of view. The technology may be identical, but the brand context changes the acceptable tradeoff.

ClickUp does some funny short-form content and social posts. That kind of humor often depends on timing, cultural awareness, and a sense of what the audience will find familiar or surprising. Maybe an AI system will eventually handle that well. Today, I’d be cautious about assuming it can.

There’s also the problem of review volume. The job description suggests that the artisan can look at 50 AI-generated options and instantly choose the two worth publishing. That sounds efficient until you ask what those 50 options are.

Are they 50 headlines? Maybe.

Are they 50 emails, 50 social posts, 50 ad concepts, 50 landing pages, or 50 videos of different lengths? That’s a different problem. Reviewing output still takes time. If one person is responsible for every marketing surface, the human reviewer becomes the bottleneck.

AI can generate faster than a person can evaluate. That doesn’t create infinite capacity. It creates a growing queue of decisions.

More output doesn’t necessarily mean better marketing

Marketing leaders often assume that if AI makes production cheaper and faster, the logical next step is to produce more.

I’m not convinced.

More content can create more opportunities, but it can also create more noise, more mediocre experiments, more brand inconsistency, and more work for the people who have to review, approve, distribute, measure, and improve it.

I’ve experienced a small version of this myself. I once over-automated a marketing system in Infusionsoft while working in higher education. The system technically worked, but the experience started to feel robotic. We had optimized the workflow and lost some of the human voice.

That’s the danger of treating AI as a production multiplier without deciding what should remain human. You can easily create a machine that publishes constantly while making the brand less trustworthy.

This is one reason I’ve written about the human loss many marketers are feeling around AI. The concern isn’t irrational. When every decision gets pushed into a system, people can feel their craft being reduced to prompts, templates, and approvals.

The answer isn’t to reject AI. It’s to be more deliberate about where human taste, empathy, responsibility, and original thinking matter most.

The real path to 100x leverage is fixing bottlenecks

The most useful idea I took from this conversation is that becoming a 100x marketer isn’t primarily about orchestrating more agents.

It’s about removing constraints.

Every organization has a bottleneck that limits what the rest of the team can accomplish. It might be slow approvals. A broken CRM. Unclear positioning. Poor lead follow-up. A lack of usable customer research. A campaign process that requires six handoffs. Or a senior leader who has become the only person capable of making certain decisions.

If you make a non-bottleneck activity 10 times faster, the organization may barely notice. If you remove the constraint holding back revenue or customer experience, the impact can be dramatic.

That’s why I keep returning to this sequence:

Find the constraint. Where does work pile up? What repeatedly delays growth?
Define the problem precisely. Don’t say “marketing is slow.” Identify which decision, handoff, system, or capability is causing the delay.
Use AI to investigate and design solutions. Let AI help collect information, compare options, document processes, write code, and expose patterns.
Keep ownership of the decision. AI can recommend a path, but a person needs to decide what the company is willing to trade off.
Measure whether the constraint moved. Productivity metrics are useful, but the real question is whether the business can now move faster or perform better.

This is more practical than asking whether AI can replace 50 people. It asks what the company actually needs to improve.

For a deeper starting point, I’d use the framework in What Marketing Workflows Should You Automate With AI First? Start with repetitive work, but don’t stop there. The highest-value use of AI is often helping you work through the complicated problem everyone has avoided.

AI should help marketers move through bottlenecks—not become the bottleneck

AI has made it much easier for me to get unstuck.

When I hit a technical problem in WordPress, a CRM, a website build, or some other system, I can usually investigate and find a path forward much faster than I could before. AI can scan documentation, explain code, suggest fixes, and help me test alternatives.

That’s real leverage. But I’m still responsible for steering the project.

Ken pointed out something that’s easy to miss: as marketers build increasingly complex AI workflows, they can become passengers in their own systems. That happened to me recently while I was working through ideas for a project. AI started taking the conversation in a direction that sounded plausible but wasn’t aligned with the actual goal.

I had to stop and say, in effect, “This isn’t the goal. This is the goal.”

That kind of correction sounds obvious, but decision fatigue makes it easy to hand over the wheel. When a system gives you a polished answer, you may accept it even if it’s solving the wrong problem.

This is where the human edge in marketing becomes practical rather than philosophical. The human advantage isn’t simply being creative. It’s knowing what matters, recognizing what doesn’t, understanding the consequences, and choosing which tradeoffs are acceptable.

Soft skills will matter more as AI expectations rise

There’s another responsibility marketers need to prepare for: managing expectations upward.

Executives are seeing bold claims about 100x organizations, autonomous agents, and teams replaced by systems. Some will assume the technology is further along than it is. If marketers don’t explain the gap, the pressure will eventually land on the team.

That makes communication with leadership a core AI skill.

Don’t simply say, “AI can’t do that.” Explain what it can do, where it needs supervision, what quality will be sacrificed, and what experiment would produce useful evidence.

For example, instead of promising to replace an entire team, propose a contained test:

Choose one marketing surface, such as lifecycle email or paid social creative.
Document the current process and baseline results.
Use AI to reduce handoffs and accelerate variations.
Keep human review and brand accountability in place.
Compare speed, quality, conversion, and team capacity after a defined period.

This approach gives leadership something better than hype: a measurable learning loop.

It also protects the team from being judged against an exaggerated promise. A marketer may be able to 10x one part of the workflow while creating unacceptable sacrifices elsewhere. That’s still valuable information.

What marketers should do now

I don’t think marketers need to become full-time AI engineers. I do think we need to keep developing practical AI fluency.

Start with the work closest to your expertise. If you’re strong in lifecycle marketing, use AI to improve segmentation, analysis, testing, and documentation. If you’re a content strategist, use it to organize research, identify gaps, and explore angles—but keep the point of view human. If you’re technical, build small tools that remove recurring friction before you attempt an elaborate agent architecture.

You don’t have to chase every new term. I can’t keep up with every new framework, orchestration pattern, agent swarm, or tool. I’ve narrowed my own focus at different points to a smaller set of tools and practical projects. That’s enough to keep learning without spending every day rebuilding the stack.

Use AI to make your existing strengths more powerful before trying to become a completely different kind of professional.

And don’t confuse complexity with leverage. If you’ve created a sophisticated system that requires constant maintenance but doesn’t move an important business constraint, you may have built yourself a new job.

That’s the opposite of 100x.

The marketer stays in the driver’s seat

ClickUp’s job posting is valuable even if the exact role is impractical today. It forces us to imagine what happens when one person can direct a large collection of AI systems.

Some parts of that future are already here. Marketers can research faster, produce more variations, write code, automate repetitive tasks, and solve technical problems with less help.

Other parts still require a great deal of human judgment. Taste doesn’t scale automatically. Brand trust can’t be reduced to output volume. And no system eliminates the need to decide what the organization should do next.

The best use of AI isn’t creating 50 more things for one person to review. It’s helping that person identify and remove the constraint that matters most.

So keep learning the tools. Build useful systems. But stay responsible for the goal, the standards, and the consequences. AI can be the hands. It shouldn’t be the driver.

Dan Sanchez: Welcome back to the AI Driven Marketer. I'm Dan Sanchez and I'm boy joined by my friend Ken Fre.

Ken Freire: Yo, what's up, bro?

Dan Sanchez: And today we're talking about being a hundred X marketer. If you didn't see from LinkedIn posts and just general news going around, is that ClickUp, yes, that big software company that is like a big I don't I don't even know what to explain ClickUp. They kind of do a little bit of everything these days, but it's kind of like an interactive, I don't know, Excel sheet in the sky kind of a thing. That's what they started as and now it does a lot of stuff. project management system. Is that fair, Ken?

Ken Freire: I I mean they try to be a

Dan Sanchez: It's like air table competitor.

Ken Freire: biased I click up is the

Dan Sanchez: You don't like click up.

Ken Freire: management system, no to make on. But that's

Dan Sanchez: I tried it once and it was clunky as I'll get out. But it's a big company. Lots of people love ClickUp. it's fine. You know, it's up there with Airtable and Monday.com. It's kind of in that realm. but they've gone all in on this AI deal and they recently posted a job description, which is kind of causing a little bit of a stir. my good friend Ashley Foss sent this to me and she's like, dude, what do you think about this? And I saw it and I was like, What? And I was like, Well, maybe, but With that in mind, I just need to read it to you. So I'm gonna read it here on the podcast, and then we're gonna talk about it because this this is kind of a big marker of what we could be looking at for the future. but we have to ask the question: is this an indicator of what's to come? Is this where we should be thinking about aiming our careers as marketers? That's what we're gonna talk about. But first, let me actually just read the job description. Okay, so it starts off from clickup, and the title of this job title is 100x Marketer. Chief Marketing Officer. Okay, so that's the title. And then we see from Zeb Evans, the CEO, we're executing on the 100X org. I'm looking for one person to own the entire brand marketing function at ClickUp, not manage a team of 50, not sit in meetings all day, not write briefs for other people to execute. One person who builds the systems that produce world-class marketing at scale and reviews everything with taste, sharp enough to know the difference between great and garbage. Good copywriting right there. Good alliteration. we call this person an artisan. What is an artisan? An artisan is not just a quote unquote good marketer. An artisan is someone with whose taste and judgment are so refined they can orchestrate AI systems at hyper speed while maintaining quality that lesser teams can achieve at any speed. Taste. They know what good looks like before it exists. They can evaluate 50 AI generated options and immediately identify the two worth publishing. They're internalizing the craft so deeply that quality assessment is instantaneous. Judgment, they know what to build, not just how. They understand the audience, the market, and the trade-offs is well enough to make high stakes calls without committees. Speed of orchestration, they don't just prompt AI, they op they operate AI systems like instruments, fast iteration loops. Rapid evaluation, continuous course correction, which takes a team fifteen team of fifteen, six weeks takes artisans days. Ownership breadth. An artisan owns a surface end-to-end. Not the social part, not the email part, the whole thing. Strategy, systems, execution, quality. Fewer people means fewer handoffs. Fewer handoffs means faster, better output. This is the marketing equ equivalent of what an a 10x engineer does. Own an entire product surface, idea to execution live. the only two things that matter. yeah, it says only two things that matter is systems, and I'm gonna spare the description of systems. Can you or essentially can you build a mark marketing system that compound? And two, review, can you judge quality at absurdly high bars? What you own, brand messaging and positioning for everything ClickUp puts into the world, campaign strategy, creative direction, and systems that execute. Execute them, social media presence, content and engagement, email marketing, drip campaigns, and lifecycle flows, content production pipelines across all formats, quality gates, nothing ships unless it meets your bar. You build systems that do it. You are the taste, the agents are the hands. So this is the job description. It is up to a CMO title, so not guaranteed CMO title, and you get about a million dollar comp growth growth path. So it doesn't even guarantee a million dollar salary at first, a million comp growth path, as in you'd grow into a million dollars. So you probably wouldn't start that at the beginning. and there's a few other things on this. I skipped over a couple paragraphs explaining systems and review, but that's generally the resume. The hundred X marketer. Ken, initial reaction to this crazy job post.

Ken Freire: I thought it was a prank. I thought they were just messing.

Dan Sanchez: Ha ha ha.

Ken Freire: I was like, well, click up does a bunch of random stuff and then I was like, it's gotta be it. It's it's gotta be like them just messing with us. But

Dan Sanchez: It could be a PR stunt, that's for sure.

Ken Freire: I wouldn't be surprised. I would be like, okay, cool. Like, it's a fun PR set. But man, I I'm honestly my my s the my real hot take was that like this person's gonna be set up to fail. Because that the I don't think the tech is there yet to do everything that this person wants to do. And you gotta find someone who's such an expert at so many different areas of marketing to be able to pull this off well. That that's my initial I mean I could go into my own rant, but I'll let you give your your your input.

Dan Sanchez: So I went and polled the audience over on LinkedIn and we've had seventy-four votes. Not a great showing on the poll, but not bad. I don't know, I haven't been regular on LinkedIn lately, so my posts haven't been getting as much reach, and that's okay. Seventy four is good enough though. And I asked I asked the crew, could a supermarketer with insane tech chops replace a marketing team of fifty people? Okay. And then I also gave some context. This is like what clickup's hiring for, and maybe it's just a PR stunt. What do you think? And but the options I gave them were four different options. Absolutely. Yes, but with sacrifices, maybe in two year or two, and then absolutely not. And the results are as following. Absolutely got twelve percent. Yes, but with sacrifices, got eighteen. Maybe in a year or two got fourteen. And absolutely not got fifty four. So well over half are like, no way, not even close. Just no. Hard no, hard pass, you know. And a a little chunk, fifteen percent, it's not a big chunk, said maybe in a year or two, they're like, someday, maybe, 'cause they're seeing where it's going. I said yes, but with sacrifices. And you know, a very the smallest portion of people, twelve percent, said absolutely not. So or absolutely. So it's kinda like I'm kind of in the absolutely yes, but with sacrifices. And like asterisk Major, massive sacrifices. Could it be done?

Ken Freire: Sure.

Dan Sanchez: Yes. Is it the best? Is it worth it? no.

Ken Freire: yeah. And and I would say like if you had a marketing team of three, it might be better. But like fifty,

Dan Sanchez: Yeah, absolutely.

Ken Freire: right? Like fifty, I'm thinking of the whole architecture. You have someone who's so specialized in certain

Dan Sanchez: Dude.

Ken Freire: areas that like you you have a great copy a copywriter, a great media buyer. You have certain people that could do such extreme specialized skills.

Dan Sanchez: Deep better.

Ken Freire: It's almost like saying to the CEO, Hey, you don't need a CMO. You could do it. Just do it have AI do it. Why don't you just have someone set up the system and then you run it? It's it's it's that logical fallacy. Like I just gotta say this before I'm done with my rant.

Dan Sanchez: If I were ClickUp's competitor, wouldn't it be funny if you were like airtable and you're like job posting the thousand X CEO?

Ken Freire: Yeah.

Dan Sanchez: Just as like a reverse PR stunt, if it is a PR stunt, you know, that would be really funny.

Ken Freire: Well, you know, like th there's two things that I that come to mind. On the the job description, they said fewer hands off means faster, better output. And I'm like, Yeah, but that you're assuming that the CMO has the ability to interpret all that output. Like if they don't, it's gonna come out like garbage. And as sooner or later it is. The second thing that I thought when I was reading this, what are all of the marketing people at ClickUp right now thinking? All their employees if they see this.

Dan Sanchez: bro, I didn't even think about the indicator of like we don't value you if you're not one of these hundred X marketers.

Ken Freire: Yeah. It it's just like should they start looking for jobs right now? Should they be on the hunt? Are they in on it? Like I there's just so stuff.

Dan Sanchez: I mean, a lot of tech companies have already been sending the signals of like we're gonna be a hundred X orgs, we're gonna be AI first, blah, blah, blah. This has been happening for over a year now. So like if you work in tech, like come on, the writing's been on the wall that this is the expectation now. So everybody better be token maxing even if productivity isn't increasing just for the appearance of token maxing productivity. Sorry, if you're working in tech, I you've been hammered lately because of this stuff. So, but everybody else has to think about it because this is sending a signal and other people, CEOs specifically, start to borrow from other CEOs. This is going to have an impact, even if it doesn't like have the like everybody starts hiring it. It's going to start making CEOs think how they evaluate marketing teams because of stuff like this. I do think it's actually possible. I even for a company the size of of of clickup. Which they need a lot of stuff. They have a lot of social accounts. They they have a lot going on. I just don't think it'll be very good. Even if that marketer is like world class. Like, so you this this person also, even if it's possible, this person's gonna be incredibly rare. Like, I've interviewed probably hundreds of marketers, and lots of fantastic marketers. There's only a few that are this good marketing-wise. And then very e there's even less that are this good and Have serious AI chops that can orchestrate agents. Shoot, I struggle to orchestrate more than one at a time, let let alone create these crazy loops. And now loop loop loops are old now. Did you hear what the new thing is? Grids.

Ken Freire: No.

Dan Sanchez: I don't even know what that is yet.

Ken Freire: Grid?

Dan Sanchez: But people are like, loops are out, grids are in. I'm like, freaking, what does that even mean? You know, have you heard?

Ken Freire: Well I have not heard of Grids, but you know, the the thing I'm thinking about with this scenario is again, if there's a CMO who could do this, why would they come work at Click Up? They're already doing

Dan Sanchez: Hundred percent.

Ken Freire: their own thing.

Dan Sanchez: That was my thought too. I'm like, okay, even if you got a million dollar compensation package out of the gate, like a million dollars a year, I don't know what I don't know. How much is that a month?

Ken Freire: what, it's probably about a hundred, a hundred K

Dan Sanchez: My gosh, it's like

Ken Freire: a month.

Dan Sanchez: almost 100k a month. It's a little less, like 90k a month. Frick,

Ken Freire: Yeah, like ninety five or twenty one. Yeah.

Dan Sanchez: it's so much money. So much money. But even if you did, that person, if you're that good that you could actually crush it, is probably a multimillionaire already. Let's be honest. If you're that good at marketing and that good at tech, you already freaking figured it out how to do it solo and scale a little small organization that creates a lifestyle that you want. Why the heck would you work for Clickup? And all of a

Ken Freire: Yeah. I

Dan Sanchez: sudden have to bend to the whims of the CEO, even if you report directly to the CEO, which you do in this position, right? So it's like, ugh, like, how are they gonna tempt this person? Now I know because I posted about it and I asked this question. You know, there are a few people that were like, yeah. And I'm like, well, I some of them I'm like, well, like, are you? I don't know if you're this person. And some of them I don't know because I don't know them at all. I'm like, well, he's like, yeah. And I'm like, did you apply? He's like, yep. I'm like, Well, I don't know you, so I can't evaluate evaluate whether you got the marketing and the tech chops. but you know, million dollar comp packages will attract people, but will it attract the person that can actually do do it? I don't know.

Ken Freire: Yeah.

Dan Sanchez: I I think they probably will try to hire this person and see what they can do. And it'll be very interesting. I'd rather do it as an experiment rather than I I don't know. Are they gonna let go of their whole marketing team? I don't know. And

Ken Freire: No, I mean if I would assume that they would have this hundred X marketer like doing their own thing. They'll have the other they'll pretty much if they were smart, right? If they're smart.

Dan Sanchez: Yes, not fire the whole marketing team and be like, shoot, maybe we can't outsource the whole marketing team to one person yet.

Ken Freire: Yeah. They would split test it, like split and check like who does better at what. But I I I have a feeling that this is a little bit more of a extreme, you know, l like let's just do a little PR stunt. This person may end up being a marketer. They they may get rid of say they have fifty employees, they might get rid of ten because this marketer cannot do this, but to have just one person, it's And with a four billion dollar company, you gotta know there's so much moving parts that it's like from a organizational and operational structure, it just sounds like this person would be working like fifteen hours a week.

Dan Sanchez: twenty four seven, three sixty five, and have a miserable life.

Ken Freire: Yeah, just to get everything set up. And they also have a similar one this

Dan Sanchez: There's just 'cause a a company this big doesn't have a lot of room for failure. So if you post something and it's not great, people are gonna point it out. You know?

Ken Freire: Yeah.

Dan Sanchez: At at click up size they would. But if you were doing this solo, like it's a lot easier because if you miss with your systems, then you know, you just recalibrate and try again. But like a company at click up size, it's a lot of focus on every social post. It's a lot of there's there's there's gonna be it that's gonna be tough to iterate on the systems.

Ken Freire: They also have another role like this called the Hundred X Chief of Staff. So

Dan Sanchez: Yeah. I didn't look at that one. But apparently you were looking at it and just before we got on, you're like, dude, they a lot of hundred X rolls. I'm like, freaking I know they have a hundred X org going on, so now I'm like, Okay. They're really pushing here.

Ken Freire: I I would have a feeling that they internally are talking to everybody and saying, listen guys, we're just testing something. They're not your jobs are not on the line.

Dan Sanchez: I hope I hope that's the conversation internally.

Ken Freire: I would hope.

Dan Sanchez: I hope. But you know, leaders bad leaders do bad things sometimes and just sort of like, This is where we're going. We're hiring these people and everybody everybody else is like, What? I need to get my resume out and leave.

Ken Freire: I should have a hundred X leader who can think like that. Like common sense one on one. Like

Dan Sanchez: It's a burn. man, it's gonna be a clickup burn. I think let's we'll talk about the good things in a second. There's some things that you really should be thinking about for this, but one more slam on this before we head into the good parts of it is you and I talked about this right just as we started, but neither of us are fans of click up the software. So, like, okay, a hundred they hire a hundred X marketer who's probably got their own systems and agents and things that they do. Are they gonna force them to use clickup? 'Cause that would be part of the sell, right? Like, you have to use click up. So even if you do find the person and tempt them with a compensation package and they come in, like, are you gonna force them to use click up? 'Cause I doubt they do. I don't know any hundred X marketers slash tech people, that are like rocking click up as their main AI home base. It's all like Claude and D files and or open claw. You know what I'm saying? Like it's a collection of tools that And they have to have a harness and it's not click up.

Ken Freire: And I yeah,

Dan Sanchez: No.

Ken Freire: I would agree with you. There there's gonna be so many different

Dan Sanchez: Yes, you could use it as a database.

Ken Freire: And you know, I will say I don't know the the Click Up ClickUp's API. I will say that. I've pre predominantly used it as the project management tool. And someone

Dan Sanchez: Mm.

Ken Freire: here might be like, well, that's why you don't like it, because everything else is great. But I'm like, that's what ClickUp was known for, was like their spreadsheets, then they move to project management.

Dan Sanchez: Yeah, yeah.

Ken Freire: Everything else has been like ancillary or they're like trying to get more money. But click up is I get why people like it, but it is clunky and

Dan Sanchez: It is very clunky.

Ken Freire: People who wanna use AI do not like clunky. They like speed and efficiency.

Dan Sanchez: To now the the way they're positioning just to jump on ClickUp's website now is the software to replace all software. So this really is the goal, that it's the database. I'm sure I'm sure it's like Yeah, they're definitely trying to come after everything. So no, you're definitely you're definitely gonna have to use clickup. I'm like, dude, hundred X marketer that's got all these agents orchestrated and tuned in, they're gonna have to learn how to use your system. That's gonna be tough. 'Cause I I haven't heard a single person in the AI space. And I'm not like paying attention to everything, but I listen to a lot of podcasts, a lot of YouTubers, I'm newsletters. I'm trying to keep a pulse on the AI space and not I I'm like I can't remember meant clickup being mentioned until this Job boasting.

Ken Freire: Yeah. I mean it looks like for Clickup, if go a high level is the the marketing SaaS product that can do all things, this is trying to be the the operational side for a business. That's what click up is trying to be. And

Dan Sanchez: Yeah. Yeah. Yeah.

Ken Freire: I'm like, you you're now going against Microsoft, you're going against, you know, just a whole bunch of different groups of people that I'm like, Good luck.

Dan Sanchez: I mean it's a big company, so a lot of people do it.

Ken Freire: And they might, but Again, I haven't found anything that I've been like, this is awesome from ClickUp. there's other products that work way smoother.

Dan Sanchez: So what I like about this job boasting is one, it's it's fun to see somebody push the envelope and try radical things. it sounds like they're betting the whole org on it. It's like, hey, sometimes bold bets win, sometimes bold bets sink ships. but it is fun to see someone it is an interesting I th thought experiment to think like, like what how would you orchestrate this? Like how could you do this right now? Like it it'd be fascinating if you're listening Like I I'm almost tempted to just like interview three marketers to see how they would do it. Marketers that I think would actually be able to pull it off. Like, okay, like there's going to be sacrifices because you can't automate ever no matter how good you are with the tech and how good you are a marketer, there's going to be things that you're just going to be able to miss. Whether your agents get it wrong or they're just know. Like remember one time I over automated Infusion Soft and we were working in higher ed and the

Ken Freire: yeah.

Dan Sanchez: loop and it got a little crazy and the the audience kind of felt like you're feeling a little robotic. That's how it's going to feel. Hundred percent. There's no way around it. Like you can't give enough voice and brand and crap and context into it to not make it feel like that. It's going to feel like that. Has to at that scale. But you know That maybe that's part of the jive. Like I can get away with AI thumbnails on my podcast because it's an AI marketing podcast. So it's like it's ex it's expected. So maybe they can get away with that because they're positioning themselves as like the master database of all the AI stuff. And they can come across this feeling a little bit more robotic. Like my thumbnails are fine being AI and no I don't pretend to be otherwise. some other brands that I manage, like I can't get away with that because their brands are more auth like I don't know, I I can't say I'm inauthentic, but like their brand because their brands are an AI, it would be perceived as inauthentic. Yeah. Right.

Ken Freire: Yeah, the more human human element to it.

Dan Sanchez: So like but I love that they're pushing into it and challenging it and coming up with the stuff. It is an interesting idea. I think eventually agents will be able to be more and more capable. So in time you're like, Yeah, I don't know, maybe. Maybe as agents get better and they have access to more context and have bigger context windows and more tools, they can orchestrate things and spin off little agent swarms and accomplish things relatively well in a way that's pleasing to you because they know your tastes and preferences. maybe. Today, that's a sacrifice. A year from now? Maybe. But there's still gonna be sacrifices in the process. But what would those sacrifices be?

Ken Freire: Yeah, I I mean

Dan Sanchez: What would they be leaving behind?

Ken Freire: I I feel like there's right now because of the way I've seen the level of AI, it feels like they're sacrificing s just about everything. Like I think they're copy. I if if you know, when I look at click up social media, they they do some funny reels or like some funny things that they do that I'm like, there's

Dan Sanchez: Yeah.

Ken Freire: a human element to that that Whoever's doing the CMO role, like I don't think AI could ever pull that off. Like that needs a human touch for comedy and jokes and just the way they frame things. I'm like, you're gonna lose that. And I think that that's I'm probably wrong, but I'm assuming that's actually worked in their favor. that they because they've keep doing it. So clearly these get they gotta have some metrics that this is working

Dan Sanchez: Yeah.

Ken Freire: for them.

Dan Sanchez: Eventually if you especially if you're doing a lot of media and video, and I don't know how much media and video ClickUp does, but I assume it's a lot, you know, with reels and all the video short posts and video ads and YouTube and they do they do I mean, I think they do even big commercials like on TV and all that kind of stuff too, 'cause they're big enough. like how do you how do you have enough time to even watch all the variations of those videos to find the ones that actually run? And then you need a certain amount of variations to run a split test. I'm like, there's not enough time in the freaking day to watch all the videos, even at 2X. If you think about it. Because AI is gonna spit out 20 and you need to find like he even said, like you need to be able to look at all the different variations and then judge the two of it of the 20. Yeah, he even said 50 pieces of output and immediately know which two are worth publishing. But what if those 50 pieces of content are all video and some of them are 30 seconds and some of them are five minutes? you're gonna be screwed. How do you have time for that? It takes too long to review everything. And that's you you become this massive bottleneck of review. Like that's and that's the problem that I'm like, there's just not enough hours in the day for one person to do this. Now, if you had only one person in charge of just video, maybe, but that person's gotta be in charge of more than video. We're talking about billboard-sized stuff. We're talking about design and social and image ads and emails and all kinds of crap. So like in order to accomplish it you have to scale everything way back into a meaningful amount of work and have to prioritize, which means you're doing less. Even though the AI agents can move faster, they can only move as fast as you can review everything.

Ken Freire: Yeah. I I my my my guess. There's there's two guesses that I have of on on this. Number one is if they find someone, it's gonna be a young person who 'cause they said like experience doesn't matter, it's just your output. Are you still

Dan Sanchez: yeah. No degree matters. No experience. No resume. no y yeah. No required. No resume. No degree. Just we wanna see systems plus review. That's it.

Ken Freire: So I I could see that there might be one guy who makes their career this launches their career, guy or gal, who it launches their career. so I could see that. The second thing I can see is they're trying to find someone super high level, but at the end of the day, they'll end up maybe taking over one depart division of marketing. Like they're gonna be crushing it in copywriting, for example, and they might get there. But like and that whole team maybe goes away. But they're not gonna like replace everything tomorrow if they found someone. I just haven't seen AI be able to pull it all off.

Dan Sanchez: Yeah, and I definitely can't pull off the video. The video part's really hard, but it takes someone working with it really closely and evaluating a lot of stuff to be able to put together one good video.

Ken Freire: Yeah. And I and I don't know a lot of marketers who are great at video who are also great at like ads copy. You know, like those are just two different skill sets that like and then like

Dan Sanchez: Yeah, there's there's probably out there. I I can I can think of there's one person who commented on my post. Let me see if I can find him, give him a shout out, 'cause I'm what did he say? It was where are you? Finn Mc McKenty. man, I love I love this guy. He's got great LinkedIn posts. Go follow Finn Mc McKenty. He's probably one of my favorite followers on LinkedIn right now. He says His this is one of the people that I actually think could do it. He says, No way. I am for sure in the top zero one percent of AI users in the context of marketing. And it's just not possible. I actually believe him. The technology isn't the issue. You could build whatever you want. It's just that no human can juggle that much context in their brain effectively. Also, if I'm replacing fifty people, I would certainly need more than one million a year. He's one of the guys that like he's financially well off enough. He's like, I freaking would never do this, even if he could do it. but again, and he's I I don't think he has previous CMO experience, but like he's worked for is it Ambercrombie, Ambercrombie and Fitch, Creative Live. he had a huge YouTube following, in the hundreds of thousands for the punk rock MBA. It's a fun channel. so like he's he's got serious chops. I've seen his posts. The guy knows what he's talking about. He's really good. he could probably do it, but he's saying no way. He's one of the people I would have nominated for it to see if it was even in the realm of possibility.

Ken Freire: Yeah. I'm with Finn. Finn is Finn is smart. Like, listen to Finn.

Dan Sanchez: Yeah. the question is will it be available to do a year from now then?

Ken Freire: Yeah, I I you know, I think putting a definite timeline might be hard, but I think that will be the future. I I think at some point it'll be able to not be just like a intern level. It'll be able to be manager director level when you have the appropriate skills to function well. I think the discernment piece, you're still gonna need someone with high level of discernment and a human individual to execute certain things about the business. I I just don't see that going away. And then even just like artistic taste, all that stuff is is needed. Like all of us know the basics of AI that you get what you put into it. so you just need those people who can put really good stuff into it to have great output.

Dan Sanchez: Yep. There's so it sounds like the consensus is it definitely can't be done now. We did have a company, solopreneur, that made a mi billion that was worth a billion dollars generating revenue in the hundred hundred maybe over a hundred million dollars for sure. And it was worth over a billion. So we have our first billionaire solopreneur, and I think he has his brother as like an executive assistant kind of a thing. So I'm still gonna count that as a solopreneur. The problem with this company was on the marketing front, he generated a lot of fake AI testimonials and endorsements, which is very unethical, and was selling like kind of questionable GLP one type products, which is a hot market, and he hammered it and did it. And it's like, okay, but the first solopreneur billionaire, while it's now technically accomplished, did it unethically in a lot of different ways. So again, that's like it was possible. But major sacrifices on ethics and integrity and quality and all that kind of stuff, to the point where it's obvious because like you had like Professor Darbrador giving endorsements with a fake looking doctor AI photo, you know. So that's how they knew. They found a bunch of like funny names in there and tried to validate that they were real Facebook profiles and social profiles of all these doctors and they're like, This is totally AI slop. So And that would that's what would happen to ClickUp if they really try to push it. Now I think based on what they're saying here, you're probably right. They're probably just gonna give them a small section and then build it out and then build it out and try to be like, That's the path, the million. If you can get up to this point, then you can earn a million dollars. But we're gonna start you here at this comp package and we're gonna give you this little section of the company to try to run with this. And we really wanna see you scale this out. I think that's gonna be the pitch, and that's how they're gonna keep themselves a little safer. Otherwise it would be way too risky.

Ken Freire: Yeah. There there's no way a four billion dollar company would just get rid of their marketing team tomorrow and hire one guy. Like maybe maybe if the person I'm gonna be pretty blunt here, maybe if the person's on crack, they would do that. But I I think click up has enough marketing chops that they wouldn't do that. That's just my my guess. Like everything that they've done, while I may not be a big fan of their software, clearly they're smarter than I am because they have a four billion dollar company. I do not, right? And they have better marketing acumen. So I'm gonna give them the benefit of the doubt in that aspect. I'm like, okay, there's a play here. And obviously we're talking about it. People are talking about it. So

Dan Sanchez: Yeah, yeah, yeah, yeah. I mean it's PR stubb, but I think it's this sounds like one of those things where they had an off site brainstorming meeting and they're trying to come up with ways to become a hundred X org. They're like, Well, let's find the best eight hundred X talent out there and see what we could do. And this was this was this is coming out of one of those brainstorming meetings for sure.

Ken Freire: Yeah.

Dan Sanchez: the question is like, what do we do about this? So let's get practical because I think people are gonna continue to think this way. CEOs are seeing this kind of stuff in their news feed. Which is going to come back to us as marketers. And I think again, it's important to be honing AI skills and sharpening them and staying up to date. It's really difficult. Like even for someone like me, and I'm pretty technical. I like keeping up to date with it, but I can't keep up with everything. So like I've just kind of honed into like Chat GPT and and Codecs, now the Chat GPT app with code mode, I guess. I and I'm using it more and more and I'm rebuilding my whole website in it. It's getting really exciting. I'm using Versell. It's like it's gr it's great. I I love it. and I'll be publishing a d podcast on that soon, on that process. So you need to be staying up to date and pushing the envelope with it and kind of just include just don't stop. Just keep learning. Try to do something new every every week, every other week or so and keep pushing it. That's good. Don't feel the FOMO when you're like, I'm not spinning up agent swarms and Designing my own SAS apps and all that kind of stuff, like, yeah, like maybe build some little mini tools, like keep going and just don't stop. and then eventually like it what's hard now becomes easy a year from now. It used to be hard to prompt, now it's not. You know, you can give crappy prompts and they still figure it out. You used to have to be super particular about how you talk to them. I spent hours refining prompts and instructions and now I don't I just word vomit, voice command into it and call it good 'cause that's easy now. but now I'm learning how to orchestrate systems and code and think through like what do I want to have happen here and how do I help the agent orchestrate it all, you know, kind of a thing. but I

Ken Freire: Yeah. The the other the other thing I was gonna mention, I don't know if I interrupted your train of thought there.

Dan Sanchez: No, go, go.

Ken Freire: But but the other thing that I would say is what practical things you could do, you obviously said number one, grow your skill set. And when I think about grow your skill set, grow your expertise before you start going

Dan Sanchez: Yes.

Ken Freire: to a different vertical, right? Like continue your expertise, whatever it is. Use AI to make that faster, smarter, like more agile. Then move to another one, another, you know, adjacent skill set. But the other other side of the coin that I was gonna mention is don't forget about the soft skill of that if you're talking with leaders manage their expectations because if they're reading this stuff, you got to be ahead of the game a little bit and be like, well, hey, actually, this is what AI is capable of. This is what they're probably doing. Like bring them back to reality a little bit. Because

Dan Sanchez: Yes. That's a very much managing up situation.

Ken Freire: it's a managing up situation. Cause if you don't do that, what ends up happening is all these people are all of a sudden going to be like, feel the pressure that now they have to perform in 100x when the tech is not even there yet. So like you might be able to ten X, but a hundred X, like, okay, let's let's everybody calm down. This is a little like hyperbole that's going on in the world right now and you're falling into it hook, line, and sinker.

Dan Sanchez: Yep. The big thing I'm communicating now is bottlenecks and constraints. And it's funny 'cause the CFOs love this con love this conversation. But essentially I'm like, we can't use AI just to be productive. We want to use AI to tackle the most com the most the biggest bottleneck holding us back, the biggest constraint that if moved makes the biggest difference. Because these are the things that we there's all these activities we have to do every week, every month. We got to continue doing those. And we can use AI to speed those up. But it doesn't matter how efficient those normal activities become if we don't address the bottleneck, which is why I'm like beating this drum on this now on LinkedIn, here on the podcast. Because if you don't fix those things, then no no amount of productivity is going to help. Like there's a constraint and you can only go as fast as that constraint. It's like You can only run a race so fast if you're doing it three legged, you know, and you have a band tied around you the reason why I say it's because I've run a six K with a three legged before. Random fact about Danchez today. 'Cause I'm weird. but that was a major constraint. You can only run so fast tied to another person, you know? And if I wanted to go faster, I'd have to cut that.

Ken Freire: Well you're getting shot. Well you're getting shot by paintballs. Who was shooting those paintballs? I won't say if it was me or not.

Dan Sanchez: That was a different race, Ken. Different

Ken Freire: What's it?

Dan Sanchez: different paintball race. Yeah. No, I didn't get shot while I was three legged. That would have been too much. Yeah, sometimes now now it's like we need story time with Dan and Ken. Our past lives.

Ken Freire: Everybody's gonna be like, Wait, what just happened?

Dan Sanchez: But you have to find the constraints of the company and then use AI help you find the problem to find the problem. Find it, define it, and then actually tackle the problem. And they're never easy. It always takes a long time to actually usually fix the constraints. There's a reason why they're constraints and they haven't been fixed yet, because they're not easy and they take time. but the more of those you fix, the better things get. Sometimes you need just a hundred little constraints fixed in order to get a big movement. Sometimes it's one big one that just takes up for freaking forever to finish. but AI can help you with all those things, but probably not in complete automated mode. They just help you with bits and pieces of it and you still have to drive. the whole project manually with help and assistance from AI, which is nice. I find I rarely get stuck anymore because AI is able to get you me unstuck so much faster. when I run into techno problems or WordPress problems or CRM problems or why doesn't this work right now problems. And you can have it scan it and bring you information and help you find the fix so much faster. It's amazing. So it's getting me through the bottlenecks faster, but that's what people need to focus on. and it's sad because I feel like this 100x marketer The the way you become a hundred X marketer is not by orchestrating agents and systems. It's by fixing bottlenecks. Because if you fix enough of the bottlenecks, you could hundred hundred X them you could hundred X the output, you know. And that's where you really should be focusing. Not spitting up systems and doing all the freaking content and stuff. I'm like, dude, that's if anything, I want to slow content down and focus like what can I do that no one else can do and then use AI to fix the bottlenecks to get more lead flow going on, you know.

Ken Freire: Yeah. And and one thing that I would encourage, you know, something that you said that I don't want people to miss is that as you're fixing the bottlenecks and using AI, it is becoming so much easier for you to lose being on the driver's seat and becoming on the passenger seat. That like people forget that you're supposed to be driving the whole situation. Dan, this happened to to me like this past week. We we were texting each other back and forth about some podcast ideas, and I was like throwing out these ideas, and you're like, this is not you this is this is AI. Stop letting AI drive it. And I'm like

Dan Sanchez: I'm like, are you leading this conversation or is chat? Because it sounds like chat's leading the conversation. You need to take the reins.

Ken Freire: Yeah, and I'm like, gosh, you're right. And then I was like, right, I gotta manhandle Chat GPT. You know, like and and

Dan Sanchez: Yeah. Yeah.

Ken Freire: had to change the thing. But even myself who's in it all day, every day, I think sooner or later we get decis decision fatigue that we want someone to just give us advice and we pivot and it's so subtle that we let AI do the work for us that we have to be mindful of that. as you're coming into it. So I think that's why when Finn said all those decisions that people need to make, I was like, he's spot on, because that's that's where people are gonna get tired. It's not that you might not have the expertise, but the 5,000 decisions that you have to make every single day for every little piece is gonna be exhausting.

Dan Sanchez: Dude, one thing that I've heard recently that's just given me so much freaking hope for the future because sometimes I do get nervous. I literally will have like not panic attacks, but I'll have like moments of like, we're all gonna lose our jobs. No one's gonna have work. Economy's gonna spiral out of control. I'm like, dude, I need to stop getting I need to get out of the news feed sometimes and go for a run. That's what I have to do to pump myself back up. but something that gives me so much hope that kinda like runs against that narrative in my head. is the fact that almost everybody I know who's like really into agents and harnesses and is orchestrating and that is freaking working way more hours. Right? And I'm like, it seems like AI is multiplying work. It ain't doing the opposite. So I'm like, I don't I don't like work ain't going away. We ain't gonna undo the curse of work. Work will always have pain and all humans are gonna have to be involved. Which is pretty much what historically has happened every time we've added new technology and automated crap. We've always just created more jobs and more work to do and more specialties and weird things. So I know this one's different because it's intelligence and who knows and it's scaling across so many different ways in so many different sectors. So like I get it. I I get why it's concerning and I still understand that. But it just seems like right now the trajectory is that the smartest people using it are working way more. They've they call AI vampires, I think, or something like that.

Ken Freire: Well and and and part of it is, you know, we we talked about this with clickup, but I everybody's creating harnesses and different tech stacks that now people are even creating their own tools because they don't want to use this tool. But like you're doing busy work and you're just adding stuff and I'm like, well just simplify life, man. Like what's the thing that you need to change? What lever do you need to pull to like grow your business or grow your efforts or or do the project, whatever you're doing? Focus on the accomplishment part, not all the things that you're doing. This happened when I was trying to, I'm rebuilding one of my websites. I literally, you know, Claude started taking me on this bunny trail and I'm like, whoa, whoa, what are we doing? This is not the goal. This is the goal. They're like, sorry, I just it just started hallucinating and taking me down the wrong path. If I would not have caught that early on, I would have probably lost three hours in my day. And I I think this is happening to a lot of people.

Dan Sanchez: So think that's good. Now I just need to go for a run and avoid getting shot by Ken in the woods.