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.

3 years ago, ChatGPT was supposed to kill content marketing jobs. Instead, content marketers are becoming CMOs.
 
That's not a coincidence.
 
In the age of AI, anyone can spin up a landing page, launch a campaign, or generate long-form content in minutes.
 
That's useful. Really.
 
But it's also made one skill more valuable than ever: storytelling.
 
The marketers who understand how to build a brand, create ownable content, and connect with an audience in a way that AI can't replicate—those are the people snagging seats at the table.

And not just in content, but across 👏 every. 👏 single. 👏 marketing. 👏 discipline.
 
(I shared more on Behind Good Content with Peter Conforti recently. Peep the clip!)
 
In fact, it's the skill I'm building Vector's entire marketing team around.
 
👾 Alex Virden is the most story-focused PMM you will ever meet. She doesn't just "do positioning"—she crafts narratives, messaging, and truly delightful content that make marketers feel seen and our product make sense.
 
Kelly Arndt's content background means he gets something most demand gen marketers miss: storytelling makes or breaks your demand gen activities. You can have the perfect targeting and the slickest automation. But if your message doesn't connect emotionally? None of it matters.
 
As B2B gets more crowded and products become more commoditized, storytellers ARE the differentiator.
 
And if you're one of us? Lean into those skills. They're more valuable than you think.

Just back from an incredible week at Above the Fold where I ran six content workshops over two days. I have but three pieces of photo evidence I was even there.

1) Schnitzel dinner with my ride or die agency guy, Justin Dunham. We've had two Zoom calls a week for nearly 5 years straight and had yet to meet in person. It was worth the wait. (For both the hang and the schnitzel.)

2) Got to meet my buddy from across the pond, Luke Winter - the man, the myth, the legend behind our "Next best way" ads. We talked shop (obvi), and concerts, and about what we do when we're not at our desks. His hair is just as fab in real life.

3) My parents were also flying out of Detroit at the same time as me - something we only realized a few days before. So we met up for an early bird special before boarding. They paid, of course, because I'm only 42. 🥰

So glad I went. So glad to be home. So ready for this damn snow to melt.

I've been a VP for all of 4 weeks.

And I'm obsessed with learning from leaders ahead of me.
 
The shift from "doing all the things" to "leading the people who do all the things" is real. I love it. But I also know there's so much more to learn.
 
Which is why I am counting down the days until Exit Five's Marketing Leadership Retreat in March.

I want to see how seasoned VPs and CMOs are building their teams, scaling high-impact programs, actually using AI (not the LinkedIn version, the real version), and proving brand value to skeptical CFOs.

Not so I can copy them, but so I can put them to work in a way that makes sense for Vector 👻.
 
March 18-20 in Paradise Valley, AZ.
 
I'll be the Hermione of the group: taking a bajillion notes and being way too eager to ask questions.
 
If you're going, let's connect. I'd love to meet you!

If you want to go, there are still a few tickets left! 
You can get yours here: https://lnkd.in/gXdGx4u3

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.

Some learning curves only make sense after you’ve lived them.


Funnel Vision was supposed to be 𝘵𝘩𝘦 thing for Vector 👻. Six months of building. A slick product UI. A beautiful narrative about contact-level intent. Launch posts. Playbooks. Customer testimonials. A scroll-stopping GIF with ghosts shooting lasers out of their eyes.
 
And then we killed it.
 
As a copywriter, you get used to having your darlings killed. But this one hurt differently.

It had been the entire company's full focus for two solid quarters, and we all believed in it wholeheartedly.

But when the data shows most customers aren't finding value, you listen.
 
The new episode of 𝗧𝗵𝗶𝘀 𝗠𝗲𝗲𝘁𝗶𝗻𝗴 𝗖𝗼𝘂𝗹𝗱'𝘃𝗲 𝗕𝗲𝗲𝗻 𝗮 𝗣𝗼𝗱𝗰𝗮𝘀𝘁 is about what happened when we swung for the fences with Funnel Vision—and missed.
 
What broke (besides our hearts lol).
How we told 180+ customers.
Why it was the right call.
And how making the wrong decision led us to exactly where we needed to be.

P.S. Sorry not sorry for swearing at you, Joshua Perk 👻

"We need an explainer video," is one of the most exciting and anxiety-inducing things a marketer can hear.

They can take forever.
They can be expensive.
They usually require buy-in from everyone and their mother.
And, because of all of the above, they need to last a while.

BUT, if you get it right, the payoff can be massive.

Because a great explainer video doesn't just educate—it gets people excited: 
"Oh my gosh, this is a different way of doing things. I want to try it." 
"They're fixing that thing that's driven me insane!"
"That was cool. I want to see more from these people." 

And if you're building something category-defining, like we are at Vector 👻, they're 10,000% worth the effort.

HUGE shout out to João Freitas and his team at MezzoLab Studio, for not only being the brilliant minds behind the video, but also making the process FUN.

If you've ever wondered...


what the inside of Vector actually looks like, how it works, and what this whole contact-level advertising thing is all about...

then Thursday, March 5 is your lucky day. 

In our first-ever Booooo-t Camp, our mother of Customer Solutions, Ally Saylor will show you the three most impactful plays you can run inside of Vector 👻.

1. Visualize who visits your site from target accounts 
2. See which ICP clicks on your paid ads
3. Create an ad audience of your entire ICP

Be sure to hydrate. 'Cause your campaigns are 'bout to get SHREDDED: https://lnkd.in/ehJJQcbN

Benjamin Watkins

Copywriter for health & SaaS companies. B2B landing pages, emails, and social ads for fast-growing health tech and SaaS companies. Dad of five adventurous kids (send coffee)

I help B2B healthcare and SaaS companies stand out with clear strategic product positioning through internal decks, a paid landing page, and a nurture sequence.

Collaborated with Tomorrow Health, Bristle Health, Focus Health, Sycle, Validic, PromptlyCheckin, and more.

"Ben is a fantastic copywriter. He understood our business and what we were looking for. He delivered copywriting that gave Opsera a voice that stood out to customers. Ben is a copywriter I highly recommend if you want results."

- Susmitha Vakkalanka, VP of Marketing of Opsera 

"Ben is awesome, folks! He went out of his way to help us get things right before launch! Hire Ben! 💯"

- Robin Singhvi, Founder of SmartCue

Founder

ThisIsCopy is a collection of the best copywriting and marketing examples on the internet.

www.ThisIsCopy.com

Just laid off my entire team today because they weren't meeting quota.

Goodbye to these fine folks:

Ben W - Head of Marketing
Ben W - VP of Sales
Ben W - Chief Revenue Officer
Ben W - Chief Copywriter

The good news is I've already found new talent that can start for me on Monday.

Say hello to: 

Ben W - Head of Marketing
Ben W - VP of Sales
Ben W - Chief Revenue Officer
Ben W - Chief Copywriter

Excited for this new team!

B2B Healthcare Positioning & Messaging | ☕️ Espresso connoisseur

My entire LinkedIn writing process changed when I changed my mindset.

I stopped repeatedly thinking:

- I can only write after a cup of coffee
- I can only write after a cup of coffee
- I can only write after a cup of coffee

I started thinking:

- I can write so much better after three cups of coffee
-.I can write so much better after three cups of coffee
- I can write so much better after three cups of coffee 

Change your coffee intake. Change the LinkedIn world.

B2B SaaS & Healthcare Positioning & Messaging | ☕️ Espresso connoisseur

Underrated hook words you should be using in your LinkedIn posts:

1. Mystify
2. Gobbledygook 
3. Collywobbles 

Examples of how to use them:

1. "Charlie can mystify LinkedIn posts"
2. "Why are you such a gobbledygook?"
3. "My dog has the collywobbles" 

Give it a try.

It's 2026 and the winter olympics still don't have AI skiing, AI figure skating, AI snowboarding, or even AI ice hockey.

Can you imagine the efficiency if we did?

Why spend years training to do a crazy triple jump or quadruple snowboarding spin when you can get AI robots to eventually do it for you without ever making a mistake?

Maybe in 2030.

Founder of ThisIsCopy.com | B2B Healthcare Positioning & Messaging | ☕️ Espresso connoisseur

The evolution of AI:

2023: "You're using AI?! You're fired."
2024: "You can use AI for spellcheck only."
2025: "You can use AI, just don't make it obvious."
2026: "You're not using AI?! You're fired."

A friendly reminder that it's never too late for an espresso.

Your Monday reminder:

- Positioning is the context that makes your value obvious
- Messaging is how you structure that context 
- Copywriting is the words that deliver it.

"What should our landing page say?"  

The better question is "what have we decided is worth saying?"

Answer questions like: 

- What's the one specific problem we solve? 
- What's the real pain we eliminate? 
- What's our actual mechanism for solving this that's unique?

Most B2B teams skip to product outcomes.

And it creates vagueness across your paid landing pages. Every vague line on your landing page is a reflection of your positioning.

Your positioning is a guide for your copy.

It tells your copy who you're for, what pain you solve, and what makes your approach different.

Because positioning is knowing what's worth saying. Copywriting is just knowing how to say it.

Your B2B Landing Page Has a Positioning Problem

I remember telling my mom and dad when I was 4 years old that I wanted to be a B2B healthcare positioning and messaging consultant when I grew up.

Wild how life turns out. 

Dreams do come true.

People ask why I only do positioning for B2B healthcare.

Because if you can position a product that's bought by committee, sold through compliance, and takes 18 months to close, you can position anything. 

That and six shots of espresso before 8am.

Healthcare companies love to add more category labels.

"We're an integration platform and a healthcare data platform and an API platform, AND we do interoperability solutions!"

Choosing a market category before you've done positioning work is what April Dunford calls tail wagging the dog.

The problem often stems from starting narrow and as you grew, you kept adding category lables instead of finding one frame that fit them all.

It could also be that you're mirroring the confusion of the market. When the market hasn't defined the label. You only mirror that confusion instead of defining it (and trying to undo assumptions).

I get it, everyone wants to place themselves in a category right away because you want to be viewed a certain way.

But you don't decide the category until you've done the work to know what value you're delivering to your market.

It's like trying to arrive at a math solution without showing your work.

You might have the right answer. You might have the wrong answer. But you'll never know if you can't trace your work (and I hated doing that in school).

"Can't we just skip to the end"

Every startup wants to give themselves a label before they've done the work. But when you do that (and you create lablel after label), you're confusing internally to your team and to your buyers. 

Start with knowing what you offer before you give yourself a definition.

This week I got an exclusive, top‑secret look at how a B2B AI startup really positions itself:

How do you make your products feel more human?

You use a simile to bridge the gap between logic and emotion. And you add parentheses to make it feel even more human (like a friend talking to a friend).

That's how you make B2B copywriting more human.

B2B healthcare companies like to jump to "here's what makes us different."

But different from what? Different for who?

Positioning has to start somewhere. And where you start completely changes the messaging that comes out the other side.

Some companies should start from the buyer's problem. Name a pain the CMO feels but can't articulate. When you nail that, your messaging basically writes the diagnosis for them. You're not selling a product. You're giving them the words for something they've been struggling with.

Other companies should start from the category. Maybe the buyer is shopping in a space that doesn't quite fit what you do. So your positioning redefines where you compete. And your messaging follows with a totally different story (one where you're not being compared to the wrong products anymore).

And some companies need to start from the broken workflow. No competitor. Just a bad process everyone accepts. Your positioning makes the status quo look wild. And your messaging becomes the wake-up call.

Most healthcare SaaS companies never pick a starting point. They just describe features and hope it resonates.

It doesn't. Because the messaging has no foundation underneath it.

Healthcare startups need to ask the right questions. 

Instead of jumping right into messaging, consider diagnosing which part of your positioning needs work.

Maybe your differentiation is unclear across the board. Maybe your buyers keep putting you in a category that you don't want to belong in.

Different symptoms require different fixes.

Flatiron Health didn't win by writing better copy. They won by narrowing to EHR for oncology. 

Veeva entered a known category (pharma CRM).

Most healthcare teams skip this step. They rewrite the homepage, landing pages, and emails when the real problem is upstream.

Building a product is not a positioning strategy.

Showing your product demo is not a positioning strategy. Creating a marketing strategy is not a positioning strategy.

Your positioning strategy defines your product and why it's perfect for that target market (and why they should care).

Think of it like this: positioning is the strategic decision about who your hero is, what enemy they're fighting, and why your product is the obvious weapon for that specific battle. 

And those decisions inform the message on your homepage, landing page, and emails.

Growing a startup without positioning is like buying flowers, chocolates, and a lovely card for Valentine’s Day without knowing who you’re giving them to . 

Value narrowness is when only your leadership team knows the actual value of your product and what it delivers (h/t to April Dunford)

The more products you launch and the more your team grows, the more you'll see if your positioning ties everything together.

Because B2B positioning is not a simple marketing exercise that is figured out by filling in the blanks of who you help and how you help. 

You have to bring your leadership team together to document how you win, your unique attributes, differentiators, who you're for, and market context.

Value narrowness is when your positioning is stuck at leadership and nobody has a true positioning deck that you can show to new-hires as you continue to grow.

Do the hard work in the beginning to figure out your positioning before it becomes a huge bottleneck.

When you know your valentine, you know what gifts to give them besides generic ones.

Generic messaging is a reflection of generic positioning.

All outcome-focused. All overly-promised focused. All wonderfully terrible.

When you're not clear on your product's positioning, then the messaging that follows isn't going to be much better.

Positioning isn't about cutting to the outcome as fast as possible. 

It's about explaining the problem in the market you're solving with your product's unique attributes to deliver a specific value to a specific set of buyers.

And you don't do that by sounding like everyone else.

You do that by getting clear on your positioning, which informs your messaging. 

But even more important, it informs how you write a landing page and an email series that speaks to specific buyers with different levels of awareness.

 I say landing pages because those are built to capture the attention of one particular audience.

And I say emails because you tell stories through emails and drive awareness through those stories.

All in all, the better you know your positioning, the better you know your messaging.

Your product's features are like shiny pennies.

You always want to keep jumping to the next one even though it takes away the clarity of how it can help your market.

For B2B healthcare, you win when you position your product around a singular story.

You're not ignoring your other features. You're giving more weight to what matters to the person who's making the decision.

Made some raspberry frangipane tart this past weekend. 

This was a good one. 

Thanks for the inspiration Harriet Shuttleworth Reis!

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