AI has made it easier than ever to be boring AF. 

That’s by design. AI is great at filling in the next pattern of a sequence.

But building a standout brand is about disrupting patterns.  

Jessica Scodary, VP of Marketing at unicorn health insurer Curative, understands the dangers of sounding like anyone else. Her company, which started as the nation’s largest Covid-testing operation, has grown to a health insurance startup built on $0 copays and deductibles.

This means Curative sells against behemoths like Blue Cross Blue Shield and UnitedHealthcare, companies with decades of name recognition. (BCBS is seriously celebrating its 97th birthday this year.) 

“Nobody gets fired for renewing with Blue Cross Blue Shield,” says Jessica. “But they could get fired for taking a risk and going on a new plan.”

When those are your contenders, relying on “good enough” AI-powered content is never going to beat out the competition. 

And most marketers know this already — they’re just trying to balance that with mandates to fold AI into their content motion and produce faster, passable, but hopelessly generic content. 

In Jessica’s words: 

“The point of a company isn’t to be in the middle. It’s to be better than that.” 

We concur. 

And there’s a way to use AI without getting dragged to the middle. 

Let’s get into it.

In partnership with

Watch the full system run live on Sep 30. Walk away ready to do it yourself.

Most founders have LinkedIn traction with nothing to show for it in the CRM. On Sep 30, Maria Gharib (Mindstream) and Valerie Chapman (Ruth AI) walk through the exact system live.

From AI-assisted content creation to sequenced outreach to booked meeting. You'll leave with a process you can run the same day.

Eligible startups also get the LinkedIn-to-Leads Toolkit: ad credits, Apollo, Captions, and HubSpot's Prospecting Agent.

Get my spot

Here’s how Jessica bakes AI into her marketing motion for efficiency gains, without brand losses. 

Means vs. end  

The higher purpose of using AI is not “to use AI.” 

(We’d like to accent this with a little amen and hallelujah.)  

And yet, a lot of marketers get bombarded with AI creations that seem to have no oversight, simply because teams are often lean and trying to ship quickly. 

“Passable” content is seductive when you’re slammed. 

But as the arbiter of brand taste, you’ve gotta hold the line.

"We definitely get a lot of, ‘Hey, I just whipped this up with AI, can you approve it?’” says Jessica. “And we're like … no, we're not approving it, and this needs to be completely redone. But thank you for experimenting." 

But that doesn’t mean AI isn’t a great means to do better, faster work. Used correctly, it can help improve the workflows that drive toward a better end product. 

“You shouldn’t measure the success of your AI implementation program purely by the amount of AI used,” says Jessica. “You should measure by the effectiveness of the output.” 

Informing vs. deciding 

AI can synthesize information from disparate sources quickly and pretty accurately. Let it inform your decisions without taking over.  

“Use AI to make better decisions yourself,” Jessica says.  

Some use cases: 

• Run a legal-risk pass on drafted comms to get a quick directional read on something — then still loop in the actual legal team

• Pull market research from across the web — then kick the tires on the findings 

• Personalize marketing collateral for different audiences – but still review before hitting “send” 

• Pressure-test messaging against a specific audience before it ships ("read this the way a skeptical broker would”) — then make sure you agree with the outcome 

• Draft a brand style guide you can use for initial alignment — then fine-tune the final version with a human eye

Speed vs. distinctiveness 

Generic AI brand content is dangerous. 

Why buy your product, when it looks as milquetoast and half-baked as 50 other products that have come on the market since the launch of ChatGPT? 

Why go with your brand, when it looks no different from the established, trustworthy incumbents? 

In marketing, there are places where distinctiveness is crucial. 

Which is why, when deciding how much of a human touch is needed, Jessica likes to ask: Is the goal of this task speed, or distinctiveness? 

Everyday internal comms, repeatable processes (like campaign briefs), and rote reporting updates are all categories where generic is fine, and speed takes priority — especially for lean teams. Good tasks to train AI up on. 

For work that needs more specificity and humanity — like PR, brand development and crisis comms, or a product launch — AI can be a starter, but the human experience and creativity should stay in the driver’s seat. 

Campaigns that got us talking: Liquid Death and Garage Beer have a plan for AI’s water problem: Drink their beverages, then mail your pee to a data center. Jason Kelce is involved. Obviously. Welcome to the pee phase of AI marketing.

👉 More on our feelings here in Crowd Work

AI spotlight: Adobe Workfront now has AI coworkers that can pick up tasks, do the work, and send it back for review. The org chart is getting weird.

Stuff that makes us scroll back up: Dan Farr made a Spotify playlist for when the stakeholder icons start appearing in your Google Doc before you’ve finished writing. No notes. Unlike the stakeholders.

Last Thursday, we hosted a live comedy special with our friends at Air and beehiiv to celebrate the launch of Crowd Work at Air HQ, with a roster of talent the late nights would drool over. And it was anything but boring.

B2B marketers CAN be funny, and they can do it on purpose.

not a dry eye in the house… or a dry glass (except for Air drinkers).

Follow us on Instagram to catch more content from the event.

Dan got us on a roll.

“Could we get an example here?”

“Would love some data.”

“Maybe we talk to someone about this?”

“Could be cool to visualize this.”

Ma’am. That is a new deliverable.

Look, there’s a place and a time for generic. 

We can appreciate a Hallmark Christmas movie, Costco-brand allergy meds, and a Marriott lobby. In some contexts, generic is kind of comforting. 

But for brand content, especially in an industry that requires high levels of trust (like health insurance), the middle is the most dangerous place you can be. Because:  

“sounds like everyone else” = “sounds like they don’t have a thesis” =
“sounds like I shouldn’t trust them” 

Defend the edges. 

See y’all next time. 

— the storyarb writers’ room 🫡

Oh! And another thing... 

The Michelin Guide was created by Michelin to get people to drive more, which meant eventually buying more tires. Michelin stars are even classified based on whether a restaurant is worth the trip.

An absolutely unhinged long-game content marketing success story.

We help brands reach thousands of B2B marketing leaders, and we turn great experts into editorial features worth their inbox space.