Kieran’s Substack - The AI Marketing Generalist

Your next marketing hire should probably surprise you

Kieran Flanagan — Fri, 16 Oct 2026 11:13:34 GMT

I’ve hired hundreds of marketers and growth professionals. Great leaders excel at hiring. It’s not just about sourcing, interviewing, or hiring. It’s about staying ahead of the curve on the skills you hire for.

A lot of the job descriptions I’ve used would need rewriting today.

Look at who Ramp brought into a marketing brainstorm: someone who had spent four years leading social for MrBeast. They ended up putting Brian Baumgartner, Kevin from The Office, in a glass box in New York doing expense reports.

ClickUp pays comedians and outside creators to join its writers’ rooms and improve its scripts.

These are software companies recruiting people who understand entertainment.

In 2021, I led HubSpot’s acquisition of The Hustle because we saw this trend. Make relevant content, not just educational.

Now, AI has commoditized so much of what we used to do. It can produce an infinite number of articles, videos, and campaigns. Your competitors have access to the same tools—the same models. You don’t even need to be a great prompter to get AI to produce pretty good results.

AI is commoditizing the consideration phase. And that changes where I’d spend my hiring budget.

I’d want people who can make our product interesting enough to watch. People who understand what our customers send to their friends. People who can convince creators with great audiences to build something with us.

When marketing moved to digital, everything became more professional. Optimized to the very last metric. It lost its edge, soul, and personality.

The battle is now in the awareness stage. To win, I’d make these three roles a critical part of my team.

Quick note: I’m going to be posting every two weeks for the rest of this year. I took on some new things. Became a best selling author. And finally reached 100k subs on YouTube. In doing all that, I need to fix my workload and I want to ensure quality is very high.

1. Viral Producer

What is it?

Someone who runs experiments that get us known. That help us win the stage above consideration → Awareness.

They take a problem our product solves and turn it into something people want to watch, participate in, or talk about. They own getting the idea made, getting it distributed, and deciding whether it deserves another investment.

Why now?

In PLG businesses, we built strong experimentation teams around sign-ups, activation, and conversion. I want that same discipline applied earlier, to awareness.

As buyers do more of their research inside AI assistants, I think being familiar before they start comparing products becomes more critical.

At the same time, AI makes parts of creative production cheaper. We can test more concepts before committing to a big production. That creates room for someone who combines a growth operator’s appetite for experiments with a producer’s ability to make things people care about.

Example

Ramp sells finance software. They put Kevin from The Office in a glass box in New York and made him process receipts by hand while a tracker compared him with Ramp.

[Brian video here]

Then came a partnership with Kumar, a retired-accountant character whose finance videos look like thriller trailers. And a Broadway musical about paying bills, starring Billy Porter.

This is the range of work I mean by a Viral Producer.

How it works

Ramp has a dedicated Creative Experimentation team reporting into growth marketing. Its current roster includes:

Kendall Tucker, Director of Creative Experimentation.
Three senior creative producers: Amber Layne, Mads Montana and Nolan Lunsford. Their backgrounds include acting, comedy, dance and YouTube entertainment.
Dallas Thompson, Influencer Manager.
Robert Lipman, Visibility Engineer.
A rotating group of freelance producers, directors, comedians and other talent.

The team owns the idea, execution and clips, and measures views, shares and downstream impact.

2. Internet Comedian

What is it?

Someone who makes your brand something customers send to their friends.

That could mean memes, short sketches, recurring characters, or an AI remix of a trend. They understand internet culture.

Why now?

Social is the new SEO

In the inbound era, you scaled via keywords and content. Now, you scale through memes and shit posting.

Basically, you have to be relevant online. The early-stage founders I speak with, pre-seed, seed, and series A, are more marketing than engineering. And they understand you need to do things differently online.

Check out this from a company called Monid.ai, whose co-founder Shengkun I met earlier this week. Their product is great. Their marketing is also great.

AI gives that person more ways to execute. They can mock up a character, edit a clip, or try several versions quickly. The valuable skill is having taste and judgment to know what would be funny in the first place.

And we’ve done this before. In 1957, Jim Henson was making puppet commercials for Wilkins Coffee. In one, a puppet refuses the coffee and gets shot with a cannon. Watch it here.

Imagine getting that through your brand review today. We’ve lost our edge.

We have better production tools than ever, and so much B2B marketing still sounds like a corporate induction.

Example

Look at how Alexandr Wang promoted Muse.

Meta’s chief AI officer turned its fluffy mascot into material for memes, pop-culture references and jokes about competitors. Business Insider counted more than 300 posts on X between Muse’s launch on September 8 and its September 23 report. Source

When someone complimented his social team, Wang said he was posting himself:

“I don’t let the corposlops near my tweet cannon.” Source

That’s the instinct you need in an Internet Comedian. Someone who sees what people are already laughing about and knows how to put our product into the joke. Obviously Alex Wang is much more than an internet comedian lol

ClickUp has built a more formal process around this. It pays comedians and outside creators to join writers’ rooms, bring ideas, and improve scripts.

How it works

This is simple: you either can do this content or you can’t. You either have this skill in-house, or you don’t.

Hire a comedic script writer. Do a contract to try it out. Look for young, out-of-college grads who understand how to create content people share.

Pay a comedy writer or creator to turn those observations into five premises. Produce a few simple versions before commissioning anything expensive.

3. Creator Deal Maker

What is it?

Someone who makes the creators your customers follow want to work with you.

They find the right talent, understand what those creators want to build and put together an offer worth accepting.

Why now?

If a creator is a good fit for your company, they’re probably a good fit for several others.

You need a reason for them to choose you and stay. That might include money, production support, access, distribution or a project they couldn’t easily make alone.

This takes commercial judgement and relationship skills. A standard sponsorship email only gets you so far.

Example

At HubSpot, one of the things we did in our creator programme was cross-promote the creators.

Being part of the programme helped them grow their own audiences. We had something valuable to offer beyond the sponsorship fee, and a reason for them to keep participating.

We also bought half their ad inventory for 2 years, locking them into long-term deals meant they had predictability on their revenue, and we got the upside on their audience growth as we had locked in the CPM cost. For example, one of our creators grew their audience 5x during those 2 years, and that was all free visibility for us.

That’s the kind of deal I’d want this person to figure out: what can we offer that becomes more valuable the longer we work together?

How it works

First, check who actually engages with the creator. Look at relevant job roles, markets and the quality of the conversations.

I built a creator grader to help with this. In one case, roughly 80% of the engaging profiles I examined had no connections and looked newly created. That was a reason to investigate before paying. A big engagement number can hide a poor audience.

Then ask what the creator wants to build. Match that ambition with something your company can genuinely provide.

Start with a paid three-part pilot. Agree the fee, creative control, usage rights and what would justify continuing.

I’d look for someone who can explain both sides of the deal: why it works for our business, and why the creator would choose it over another offer.

Before opening your next marketing role, put a small budget behind one of these experiments.

Commission an entertaining product concept. Bring a comedian into a writing session. Build an offer for a creator you’d love to work with.

You’ll learn far more about the skills your team is missing by making something together than by rewriting the same job description you used last year.

Until Next Time,

Happy AI;fying

The Creative Context OS: How to Stop AI From Making Your Content Sound Like Everyone Else’s

Kieran Flanagan — Fri, 02 Oct 2026 10:57:03 GMT

Creating content is one of the biggest parts of a marketer’s job. Recent AI models have created a strange problem for writers.

The models are getting much better at creating content. And that’s exactly why so much of the content we’re seeing is getting worse.

Hundreds of thousands of people now use the same handful of models to write LinkedIn posts, newsl…

Is the Traditional Marketing Team Dying, Shrinking, or Turning Into Something Else?

Kieran Flanagan — Fri, 18 Sep 2026 11:12:43 GMT

After “Is the CMO role dying?”, the number one question I get asked most is what happens to the marketing team. How drastically will it change? And is it going to shrink in size?

In May, I published a first draft of an answer: how to rebuild your marketing team for the agentic age. It consisted of four layers. Context, Execution, Orchestration, Leadershi…

The CMO Role Is Dying. Here's Why I Think That's Temporary.

Kieran Flanagan — Fri, 04 Sep 2026 10:40:18 GMT

The number one question I get asked right now is whether the CMO role is dying.

I hear it from marketers in my DMs, WhatsApp messages, and emails, all wanting to know whether they’ll end up reporting to a sales leader in the future. I hear it a lot from my founder friends, mostly in SF, who’ve told me their plans to split marketing between product and sa…

I Built an AI System That Positions Your Product

Kieran Flanagan — Fri, 28 Aug 2026 11:03:19 GMT

G2 lists 200,000 software products right now. Two thousand categories. And AI is causing this to accelerate; 20,000 new AI products appeared in a single year, a 391% spike. Every software category is being flooded with new entrants that all sound the same.

An explosion of sameness.

Wynter surveyed 100 B2B marketing leaders this year. 86% rated their own c…

How to Build Your Starter AI Marketing System

Kieran Flanagan — Fri, 21 Aug 2026 11:06:36 GMT

It’s a tough time to be a marketer. The overwhelming online narrative is that there are many ways you’ll lose your job and become obsolete. Your job disappears if you’re not AI-native; if you’re not a systems builder. AI means you don’t need a CMO or even a marketing leader.

The above narrative is everywhere. If you’re a marketer trying to build a career…

How I Built My Marketing Intelligence Layer (+ The Skill and Template)

Kieran Flanagan — Thu, 13 Aug 2026 10:49:21 GMT

I’ve spent 15+ years accumulating marketing experience. It lives in a sprawling mess, across the parts that become the unconscious way I do marketing, the sprawl of learnings across Google Docs. Presentations. Meeting notes. Slack threads. Random files. And most of it is lost.

That’s just how things worked.

Today, that intelligence is the most valuable as…

The State of B2B Marketing. What's working & What's not.

Kieran Flanagan — Thu, 06 Aug 2026 11:42:30 GMT

B2B marketing is changing at a rapid pace.

I’ve recently spent a bunch of time with founders and other marketing leaders. These are my unfiltered notes on the state of B2B marketing now. What’s working and what’s not.

1. Brand / Product Positioning.

The challenge for all brands right now is that AI is consuming all the online oxygen. ChatGPT and Claude alo…

Use AI to Craft ‘Slop’ Free Content

Kieran Flanagan — Fri, 31 Jul 2026 10:55:11 GMT

Brian Chesky (CEO of Airbnb) got called out for “claudeslop” last week. What’s funny is people were angrier that he supposedly used Claude to create his X thread than the fact that he was promoting a crypto scam.

It turned out his account was hacked, but we’re seeing a growing anti-AI sentiment when it comes to using AI to create content. People call it …

I Built a Claude Skill to Show Me Why My LinkedIn Reach Collapsed

Kieran Flanagan — Fri, 24 Jul 2026 11:06:17 GMT

Anyone building a personal audience through content has, at some point, been whacked by algorithmic changes. This is happening on LinkedIn all the time as they attempt to deal with the onslaught of AI-generated content.

The Pangram Labs study (published July 9, 2026) scanned over 1 million posts across five platforms. LinkedIn was the most AI-saturated b…

The Great AI Sprawl

Kieran Flanagan — Fri, 17 Jul 2026 11:05:13 GMT

In the early days of AI, every company had one directive for their people - BE AI NATIVE. Most of them got the opposite of what they expected.

Not more productivity. More chaos. A tangled web of ‘AI Sprawl ‘.

Everyone turned into an AI builder overnight. Some did it because it was now a big part of how they got promoted. Some did it because their team was…

I Built an AI Skill to Sharpen My Taste. Here’s how it works.

Kieran Flanagan — Fri, 10 Jul 2026 11:10:08 GMT

One of the first meaningful things I built with AI is a content system. I documented some of the system here. And I’d still be the first to say AI will always disappoint if you’re expecting a finished article, social post or tweet.

But I still believe there is real value in AI for content, in its ability to build a profile of your audience, better unders…

The Rise of the 'AI Brains'. And Why Everyone Is Building One.

Kieran Flanagan — Fri, 03 Jul 2026 11:10:06 GMT

When Andrej Karpathy posted about building an “LLM Wiki” in April and garnered 19.6 million views, he started a trend: an army of geeks building their own “AI brains.”

I’m one of them. So is Brian Halligan, the former CEO of HubSpot and now partner at Sequoia, who revealed he’d built an AI agent trained on his entire life that now attends his Zoom meeti…

If I Had to Build My Audience From Zero Today, Here's What I'd Do

Kieran Flanagan — Fri, 26 Jun 2026 11:17:57 GMT

I’ve built a largish personal audience across Substack, YouTube, and LinkedIn. If I had to start from zero today, with AI flooding every platform, here are the principles I’d follow.

These have been learned through years of grinding, and iterating to figure out how to scale a personal audience through content.

Where applicable, I’ve added in skills from …

Stop outsourcing your marketing intelligence to AI. Do this instead.

Kieran Flanagan — Thu, 18 Jun 2026 11:10:26 GMT

Satya Nadella published something last week that speaks to how a modern marketing team will win once all teams are rebuilt around AI.

The title of the post was “A frontier without an ecosystem is not stable.” It sounds like something written for a CTO.

But it’s as applicable for anyone working in marketing.

Buried in the post is the clearest description I’…

3 Marketing Jobs Worth Paying 2x For: A Fable 5 UseCase Guide

Kieran Flanagan — Fri, 12 Jun 2026 10:53:06 GMT

The model releases just keep coming. All our feeds are awash with hype videos for Fable 5, anthropic’s latest model. And that hype is justified. The model does, from the small amount I’ve read and tested, seem incredible.

However, Fable 5 does deserve a different conversation. It’s a new class of model - the first Mythos-class model Anthropic has release…

How to Build Your Career in the Age of AI. You’re Being Lied To

Kieran Flanagan — Fri, 05 Jun 2026 11:03:16 GMT

Every podcast, tech billionaire, and AI influencer is saying the same thing about careers in the AI era. Work harder. Have agency. Adapt or die.

Almost all of it is being written by a group of people who’ve already made their money, had great careers, and aren’t under the same pressures as people still trying to build one.

I want to tell you why this nar…

How to Rebuild Your Marketing Team for the Agentic Age. Full Breakdown.

Kieran Flanagan — Fri, 29 May 2026 11:20:31 GMT

Most marketing leaders are trying to fit AI into their existing org. New AI assistants, tools, and agents, same old team boxes. It means you’re bolting AI onto a structure that was designed to do one thing: coordinate people.

That’s a mistake.

If you integrate AI into how a team works, you’ll get minimal results. I believe you have to rethink how the team…

The 4 New Claude Code Features for GTM Operators

Kieran Flanagan — Fri, 22 May 2026 11:05:56 GMT

Anthropic has been shipping a whole host of new features in Claude Code that are ‘gold’ for GTM operators, but you’ve likely not heard or used them yet. What I’m going to show you in this post is some of the best features shipped over the past 90 days and how to use them as GTM operator, whether that’s marketing, growth, or sales.

What shipped in the las…

Agentic-Led Growth: A New Model for How B2B Companies Grow

Kieran Flanagan — Fri, 15 May 2026 11:14:48 GMT

Everyone is frantically adding AI to their GTM. Very few are running a true agentic-first GTM. It’s the difference between integrating AI and reorienting your GTM around it.

We’ve seen this happen before.

When factories first got access to electricity in the late 1800s, most of them didn’t redesign their operations. They just replaced the steam engine wit…