Head of Content @ LASSO | Co-host of That's Marketing, Baby | Delivering daily cheat codes for small content teams

I'm a creative director turned content marketer and strategist with more than 20 years of experience conceptualizing and executing breakthrough work for B2C brands like Eggo, Rice Krispies, Blue Cross, Cottonelle, and McDonald’s, and B2B brands like Fastly and Island.

I have a knack for leading cross-functional teams toward a common goal, bringing order to the oft-chaotic creative process, crafting insight-driven global campaigns, and bringing stories to life via long- and short-form content.

Jess Cook

I've worked with a lot of talented people over the years.
 
But every once in a while, you meet someone who just 𝘨𝘦𝘵𝘴 𝘪𝘵 in every way that matters.
 
Annalisa Rodriguez is one of those people.

I had the privilege of working with her for a short time at Fastly.
 
And this week, she joined Vector 👻 as our Sr. Content Marketer Manager — a sentence that makes me so happy I could cry.
 
Annalisa has a journalism background that shows in everything she touches. Long-form, repurposing, content design... she's equally amazing at all of it.
 
But what makes her truly special is her ability to take the things people 𝘴𝘢𝘺, turn them into content that makes readers 𝘧𝘦𝘦𝘭, and connect it all to results when buyers 𝘢𝘤𝘵.

(Read: not a common skill.)

Bonus: she's already vibing with us in Slack, and keeping our cat-loving hearts fed with pics and videos of her kitties, Oreo and Darkness. 😻
 
With Annalisa on the squad, we now have four marketers at Vector. And for the first time, a real three-legged stool:
 
→ Product marketing 
→ Demand gen 
→ Content

(i.e. I feel like I just collected ALL OF THE POKEMON.)

Annalisa's going to be sharing how she builds content here at Vector. You'll want a front-row seat for that, so go give her a follow.

Then stand back, 'cause sparks are 'bout to fly, y'all.

I have a rule I live by in marketing: Test small before executing big.

It's why I ran an influencer pilot before making it a full program.
Tested new messaging in ads before our repositioning launch.
And why I'm so excited about what we're announcing today...

Vector 👻 𝗶𝘀 𝗽𝗼𝘄𝗲𝗿𝗶𝗻𝗴 𝘁𝗵𝗲 𝗰𝗼𝗻𝘁𝗮𝗰𝘁-𝗹𝗲𝘃𝗲𝗹 𝗱𝗮𝘁𝗮 𝗯𝗲𝗵𝗶𝗻𝗱 𝗖𝗹𝗮𝘆 𝗔𝗱𝘀. 🎉 

Here's the metaphor that's been living in my head for this:

Clay is the proving ground. 🏁
It's where GTM teams experiment with signals, build enrichment workflows, test what actually predicts buying behavior, and figure out which audiences are worth activating.

Vector is the Autobahn. 🚗
Once you know what works? You open it up. Contact-level targeting, live audience updates, suppression logic that actually follows your buyers—running modern ads playbooks at full speed.

This isn't hypothetical for us.

It's exactly how Kelly and Sara have been building Vector’s ads program.

• Kelly uses Vector to identify accounts and contacts signaling intent. 
• Sara uses Clay to enrich and score those ICP contacts. 
• Then, they use Vector to activate those contacts across LinkedIn and Google, keeping our paid targeting aligned to real buyer signals as they move through the funnel.

When your team’s already living the use case, you know you're onto something.

Grab some time to see it in action: https://lnkd.in/eugn7rJh

I love a good Uno reverse. 

Especially when it's aimed at Joshua Perk 👻.

In the season two finale (!!!) of This Meeting Could've Been a Podcast, Josh and I take you through our entire website redesign process: from the awkward "you literally told me no when I suggested this six months ago" conversation (haha), to how we worked with our design agency to build the new look and feel, to the 37-item launch checklist 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 (Josh) did not see coming.

But one of my favorite takeaways from the entire project goes a little something like this...

The second someone lands on your site, they start to form an opinion about your product. 𝗔𝗻 𝗼𝗽𝗶𝗻𝗶𝗼𝗻 𝘆𝗼𝘂𝗿 𝘄𝗲𝗯𝘀𝗶𝘁𝗲 𝗺𝗮𝗸𝗲𝘀 𝗳𝗼𝗿 𝘁𝗵𝗲𝗺.
 
They assume the same level of polish and thought put into your website go into your product, too.
😒 If the design feels dated, they assume the product UI is clunky.
😒 If product screen shots feel too mocked up, they assume the product isn't robust enough.
😒 If it's hard to figure out what you do, they assume the product is just as convoluted.

A lot of teams either go full nuclear on a redesign and lose everything distinctive about their brand, or they're so precious about what they have that the "redesign" is just a fresh coat of paint on the same old house.
 
So when Josh and I sat down to figure out what to actually change, we built three buckets.
 
𝗕𝘂𝗰𝗸𝗲𝘁 𝟭: 𝗞𝗲𝗲𝗽. These are the things that make you you. The stuff your audience would immediately recognize and miss if it disappeared. You don't want to lose them—you want to evolve them. Same personality, better haircut. For us: Ghostie, bright colors, bold statements with a wink.
 
𝗕𝘂𝗰𝗸𝗲𝘁 𝟮: 𝗚𝗹𝗼𝘄 𝘂𝗽. These are the things that aren't bad, exactly—they're just limiting. They paint you into a corner or kill your flexibility, even if people associate them with your brand. For us: super saturated color usage that made text basically impossible to read.
 
𝗕𝘂𝗰𝗸𝗲𝘁 𝟯: 𝗥𝗲𝗽𝗹𝗮𝗰𝗲. These are the things actively working against you. They're building a perception you don't want—making you look smaller or less sophisticated than you actually are. No sentimentality. They gotta go. For us: all-caps headlines and ghost visuals in spots that should have had actual product screenshots.

The reason I love this framework is it gives you permission to make bold changes while protecting the things that actually matter. Before we kicked off the project with our design agency, Josh and I literally listed out which parts of our brand fell into which bucket. It made every every design decision after that so much cleaner. 🤌

The FULL second season of is out now! Just search This Meeting Could've Been a Podcast.

CMO @ Heatmap.com

Building the future of creative operations @ CreativeOS. Using this machine to make the world a more creative place through less busy work and more time to create!

Chase Mohseni

I've seen brands spend $30K on a video shoot and get beaten by a product shot with three arrows on it.

That's basically what happened here.

Hiya's kids sunscreen ad is two hands holding a tin and three callouts. Headline says "Fits Any Routine." 

There's nothing impressive about it creatively.

But it's doing exactly one job at exactly the right moment - answering the three questions a parent has right before they buy:

Is it messy? No. 
Can I carry it? Yes. 
Does it work for real life? Beach, park, school days - yes.

No desire creation. No lifestyle fantasy. Just objections killed cleanly.

This is what I think about every time a brand asks me why their retargeting isn't converting. 

Nine times out of ten they're running inspiration ads to people who already want the product. 

Those people don't need a mood board. They need one last question answered.

Know what job your ad is doing. 

Everything else follows from that.

Founder/CEO @ CreativeOS - streamlining your creative process.

Tomorrow I am jamming with Sarah Levinger and Matthew Gattozzi
 about all things ads and creative strategy on Creative Playbook from CreativeOS

If you want to get better at turning those impressions into conversions - come join us. (Sign up in the comments)

I keep seeing the same ad creative mistake everywhere.

Broad creative → collection page → zero conversions.

No focus = no conversion.

Here are 3 insights that came up during Creative Playbook this week with Sarah Levinger & Matthew Gattozzi:

1. The fatal mismatch

Everyone is making broad ads with no angle and sending them to the broadest page possible (collections, best-sellers).

Then wondering why nothing converts.

No focus = no conversion.

The fix: Match your creative to your page type. Static ads need deep landing pages. Video ads can work with simpler pages. And collection pages only work when people already know your brand.

2. Sell to the buyer, not the user

This came up on the STEM kit breakdown and it's the mistake most kids product brands make.

Parents don't buy STEM kits because their kids need physics lessons. They buy them to feel like good parents investing in their child's confidence.

Show the kid's face when they crack the code. Show "my kids are asleep—look at what they built tonight."

The parent is the buyer. The kid is the experience. Sell emotional ROI.

3. Category psychology matters more than you think

Jewelry ≠ kids products ≠ supplements. Different products need completely different approaches.

Example: Jewelry is one of the only categories where consumers want it to be expensive. Don't sell attainability—sell exclusivity and craftsmanship. And for the love of god, use harsh lighting to make stones sparkle. Soft lighting kills jewelry ads.

If you’ve made it this far and want to do deeper - get your full breakdown here.

I've been thinking about how all marketing strategy looks the same now.

Same playbooks. Same hooks. Same templates. Same "proven frameworks."

Then I read about Hermes - they've been in business for 186 years.
Worth $220 billion.

No marketing department. No ads. No discounts. Ever.

One sentence from a former CEO explains why:

"We don't have a policy of image. We have a policy of product."

Here's what that means for you today...

In 1837, Thierry Hermès opened a harness workshop in Paris.

He wasn't building a fashion brand.

He was solving a problem: horses' movements were hampered by poorly-sized equipment.

His solution was the saddle stitch — two needles, two waxed threads, tensile opposition. Only done by hand.

One stitch became the foundation of a $220B company.

Not a logo. Not a slogan. A stitch.

By 1919, the automobile was killing the horse industry.

Most equestrian businesses panicked. Pivoted. Chased trends.

Hermès asked one question:

"What can we make with our hands here that will interest our clients today?"

Not: what's trending? Not: what are competitors doing? Not: what does market research say?

What can we make with our hands?

The most iconic bags in luxury fashion history were never designed as fashion.

The Haut à Courroies (1892) — designed to carry saddles.

The Bolide (1923) — first bag with a zipper. Designed so things wouldn't fall out during travel.

The Kelly — designed in 1935 as a "ladies' bag with straps."

No campaign brief. No focus group. No influencer strategy.

They made functional things beautifully. Fashion came later.

Here's what kills me:

Hermès made the Kelly bag for 20+ years before it became famous.

It wasn't even called the Kelly until 1956.

They didn't need the world to validate the product.

They trusted the craft.

While everyone optimizes for speed, Hermès built the opposite model.

One craftsman makes each bag. Start to finish.

A Kelly takes 18-20 hours of handwork.

New artisans don't touch a product for sale until they've apprenticed for 18 months to 4 years.

Slowness wasn't a bug.

It was the brand.

By 1935, Hermès had survived an entire industry dying.

They did it without:

→ A marketing department 
→ A single advertisement 
→ A discount, ever 
→ A product designed by committee

They only asked one question: "How do we make this better?"

The selling took care of itself.

Here's what this means for you today:

Everyone's asking "how do I market this?"

The better question: "Is this good enough that marketing becomes irrelevant?"

In a world of AI-generated everything, craft is the last moat.

Speed is the default. Slowness is the differentiator.

Make things no one asked for — but everyone needs.

Trust the work before the market validates it.

Hermès spent 20 years making bags nobody cared about.

Then they became the most valuable brand on earth.

Patience isn't a weakness. It's the whole strategy.

I recently looked at a funnel from Caraway Home (love them) for their airtight food storage containers.

At first glance, everything feels polished. The brand aesthetic is strong, the product photography is beautiful, and the experience feels premium.

But when you look at the ad → landing page transition, there’s a subtle breakdown that many eCommerce brands make.

The Ad

The creative leads with authority:
“Trusted by the Experts” + Good Housekeeping Award Winner.

It’s a powerful trust signal. The image reinforces the message too - the containers are shown in a real pantry environment, communicating organization, freshness, and everyday usefulness.

So the click motivation is clear:

This is a trusted, expert-approved storage solution.

The Landing Page:

After clicking, the user lands on a standard “Shop Food Storage” category page.

Instead of reinforcing the authority message, the experience immediately shifts to:
• filters
• product grids
• quick shop buttons

The funnel goes from persuasion → browsing.

That’s where the coherence drops.

What Works Well

• The product visuals match the ad perfectly
• The brand aesthetic is consistent (clean, premium, minimal)
• Users can quickly see product options, pricing, and ratings

So visually, the experience is cohesive.

Where the Opportunity Is: The landing page doesn’t continue the story that drove the click.

A few small changes could dramatically strengthen the funnel:

- Carry the authority message forward
- A hero section like “Award-Winning Airtight Storage” with the Good - Housekeeping badge would reinforce the click motivation.
- Introduce the category before the product grid
- A short benefit section explaining freshness, non-toxic materials, and pantry organization would turn the page into persuasion - so it's not not just browsing.
- Highlight a starter set or best-seller first

This reduces decision scroll fatigue and gives users a clear starting point.
The takeaway

This is a common pattern in DTC:

Great ad → solid product page → missing persuasion layer.

The funnel looks coherent, but the message continuity breaks after the click.
Often, the fastest conversion wins come from fixing that moment.

Curious how others handle this:

Do you usually send paid traffic to product pages, bundles, or category pages?

You're not stretching your creative limits. 

Don't argue - we both know it's true.

You make things with the intention of completing your work. That's it. It's natural.

I've set out to change that for myself. The challenge - create 3 new things a day using CreativeOS + a few other tools.

And I can't start with making things for my own company. It has to be for others to force me see the world differently. And argue for the angle I am taking.

Why: we get locked in the day to day too often - we don't allow ourselves to stretch our creative minds - and our work gets stale.

The interesting outcome has been seeing the gaps in my creative ideation. Seeing what I'm drawn to and the gaps in my natural creative inclintations.

I'm going to keep doing this weekly and share what I learn from it. 

Want to join me? 

creative this week made for: Ramp, Grüns, Nike, Metafit | TrimRX, and Parachute Home

Going to get more colorful next week!

Money printing websites is the goal.

How you do that: Come to Creative Playbook with me, Shaun Brandt, and Taylor Davies from Oddit & CreativeOS.

Learn what makes website great or not so great. There will be plenty of both. 

See you there tomorrow at 11am PST.

Link to sign up in comments.

I used to work in manufacturing during college. Traveled to China. And at the time, the pace of innovation felt genuinely wild.

You could video call a factory in Shenzhen, hold up a camera to show them what you were looking at, share files back and forth in real time, and they’d be prototyping on the floor within hours. 

That felt like magic in 2007, 2008.

Today at CreativeOS , we have our version of that. A customer drops async video feedback. It hits our team channel. 

We jump into a voice room, talk it through, get aligned. 

Someone pulls the specs together, APIs get connected, a design gets rendered, code gets pulled. All of it lands in staging for testing.


Start to finish: a few hours.

What blew my mind two decades ago now feels like table stakes. And I think that’s actually a beautiful thing.

Innovation isn’t a threat when you’re in service of people trying to build something real. (Pls read this again)

It’s just the game moving forward.

Happy Friday.

NYU just studied 106,000 ad impressions to figure out if AI-generated ads actually work.

The results are wild.

And they basically prove what I've been saying.

Here's what they found:

Fully AI-created ads outperformed human-made ads by 19% in click-through rate. 

Not in a lab. In real Google Ads campaigns across two brands.

But here's where it gets interesting.

AI-modified ads - where a human designed the ad and then AI "enhanced" it — performed NO better than human-only ads. In some cases they performed WORSE.

Read that again.

The WORST way to use AI in your creative process is as a touch-up tool. A little background swap here, a quick enhancement there. 

The research calls it a loss of "ecological validity" — basically the ads start looking uncanny. 

Your brain knows something is off even if you can't articulate why.

The BEST way? Let AI create from scratch with clear creative direction. Then layer in your brand, your taste, your judgment.

One more finding that should scare the slop merchants:

When consumers were TOLD the ads were AI-generated, effectiveness dropped by 31.5%.

Let that number sink in.

31.5%.

That means the brands pumping out obvious AI slop aren't just producing bad creative. 

They're actively training consumers to distrust their ads. Every generic AI-looking image is a signal to scroll faster.

Here's how I think about it:

There are three lanes right now.

Lane 1: Human-only. Slow. Expensive. Doesn't scale. The research confirms it's no longer the best option.

Lane 2: AI as a band-aid. Tweaking human work with AI tools. The data says this is actually the WORST approach — you get the uncanny valley without the upside.

Lane 3: AI as a creative engine with human taste as the filter. 

Start with AI. Direct it with real strategy. Layer in brand. Test at volume. This is what won in the study and it's what's winning in the market.

The brands that figure out Lane 3 are going to have a massive advantage.

The brands stuck in Lane 2 are going to wonder why their "AI-enhanced" ads keep underperforming.

And the brands in Lane 1 are going to get priced out by the speed gap.

The future of creative isn't human vs. AI.

It's taste + AI vs. everyone else.

Which lane are you in? 👇

The brands overthinking creative are losing.

But so are the ones pumping out AI slop.

And somehow nobody's talking about the middle.

Here's what I see running CreativeOS - there are two types of brands getting absolutely crushed right now:

Brand A spends 3 weeks on a single ad. Endless revisions. Pixel-perfect. They launch 1 concept, pray it works, and wonder why CAC keeps climbing.

Brand B discovered AI and now they're shipping 50 ads a week that all look like they were made by a microwave. Same generic hooks. Same stock-looking visuals. Zero brand. Zero soul.

Both are losing to Brand C.

Brand C gets it. They move fast AND they give a damn. They start with proven structures - not a blank canvas, not a ChatGPT fever dream. 

They put their brand into it. Real voice. Real angles. Real creative decisions made by a human who understands their customer.

Then they test at volume.

The difference is massive:

1) speed without slop
2) volume without looking like everyone else
3) templates as a starting point, not a final product
4) AI as a tool, not a replacement for taste

(Hot take: the brands that use AI to SKIP the thinking are going to get wrecked by the brands that use AI to do MORE thinking, faster.)

The bar for creative is about to split in two. The slop merchants will race to the bottom. The brands with real taste and real speed will pull away from everyone.

One more thing.

If your AI slop ads are "working" right now - don't get comfortable. That's arbitrage. You found a window where the bar is low. That window always closes.

The brands building real creative muscle right now are going to eat you alive when it does.

Where are you seeing the most AI slop right now? I have thoughts 👇

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