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

Ya girl has a new title:
 
VP, Marketing at Vector 👻
 
And while I do my office chair happy dance, I see this as part of a larger and very exciting trend.
 
The next generation of B2B marketing leaders 𝘄𝗶𝗹𝗹 𝗯𝗲 𝗰𝗼𝗻𝘁𝗲𝗻𝘁 𝗺𝗮𝗿𝗸𝗲𝘁𝗲𝗿𝘀 because brand and storytelling have become non-negotiable for growth.
 
In a world where being forgotten is the most expensive problem you can have, the marketers who can: 
→ Tell a story that sticks 
→ Build brand that competitors can't replicate 
→ Create content that makes people feel something
 
... are the ones that smart founders and CEOs will want leading the charge.
 
So to all my fellow content people out there wondering if you can make the leap to marketing leadership:
 
👏 This 👏 is 👏 your 👏 moment.
 
Your ability to translate audience insights into ownable marketing moments is not a nice-to-have anymore.
 
It's the underpinning of modern marketing strategy.
 
And I'm crazy excited to keep proving it with the entire Vector team.

I found this random tool online that lets you create videos that look like they're breaking through your LinkedIn feed.
 
Cost me $40.
 
Figured, what the hell. Let's try it.
 
So I made this little video ad of our ghosties lounging in a pool with a unicorn floaty that "breaks through" the bottom of the post and floats across your feed.

And people 𝘭𝘰𝘴𝘵 𝘵𝘩𝘦𝘪𝘳 𝘮𝘪𝘯𝘥𝘴.
 
The comments weren't about our product. They weren't even really about the message.
 
They were about the ad itself:
• "Ok, the unicorn floating out of the post got my attention... very clever!"
• "Broke my brain in the best way!"
• "I am HERE for that unicorn!"

Which is either a total failure or the most successful awareness ad we've ever run, depending on how you look at it.
 
But with:
• 100k+ impressions
• 6-second dwell time
• 2.6% CTR
• 3% engagement rate
... I'm going with the latter.
 
I think about this ad a lot when people talk about needing huge budgets to do "creative" B2B ads.
 
The tool was $40. The video took maybe an hour to put together. The ad spend was $5k over the summer.

And it's still one of our most memorable ads.
 
All while companies out there spend $50k on a single piece of "premium" content that looks exactly like everyone else's premium content and performs exactly how you'd expect: meh.
 
What if you just tried something weird instead?

Things that have me 🐝 buzzing right now:

• I FINALLY hired a Demand Gen marketer and they start in two weeks! (Any guesses who? 😏)
• Vector's 2026 all-company kickoff is TODAY! 
• We're doing a LIVE episode of This Meeting Could've Been a Podcast on 1/14 - you comin'?
• My kids went back to school! (Hallelujah. I love them. But it was time.)
• The Stranger Things finale still giving me all the nostalgic feels

What's making this first Monday of 2026 a little less Monday-like for you?

Here's what's keeping me up at night lately:
 
All the things that put Vector 👻 on the map—the podcast, the bold ad creative, the swag—operated mainly on vibes.

They happened (and worked) because we moved fast, took risks, and didn't overthink it.
 
But now we're growing. Trying to triple what we did last year.
 
Which means we 𝘢𝘭𝘴𝘰 need the stuff that doesn't feel sexy but absolutely matters: processes, documentation, scalable systems, the "grown-up" marketing operations.
 
And I refuse to let building those things kill the magic.
 
Even though I know that's exactly what happens to most B2B brands as they grow.
 
They trade "let's try it" for "let's run it through legal." They trade bold for safe. They trade memorable for committee-approved.
 
I'm determined to figure out a different path.
 
Here's how I'm trying to think about it:
☝️ We can't sacrifice momentum for maturity. We have to figure out how to do both.
✌️ The cool stuff is what gets us noticed. But the systems are what let us capitalize on it.
 
So I'm working on: 
→ Protecting time for experiments (they stay sacred) 
→ Building repeatable frameworks for what's working (so we can do more of it) 
→ Hiring people who get excited by BOTH sides of this equation
 
I think the trick will be to figure out which magical, vibey things work the most, and scale them without diluting them.
 
Still figuring this out. (And will be for the foreseeable future lol) 
But that's what's keeping me up.

When Eric Linssen introduced me to Kelly Arndt, I was on month five of searching for THE demand gen marketer to join the Vector team.

I had a lot of boxes this person needed to check: 
→ Ads expert who could stand up and scale our paid engine
→ Mad scientist who could run Vector for Vector
→ Charismatic ambassador who could share our own use cases with customers and prospects
→ Player coach willing to build in public alongside with the rest of our marketing team
 
I wasn't going to settle. I wanted top 1% talent, and that meant being patient.
 
I interviewed 30+ demand gen marketers. All incredibly talented, some we came thisclose 🤏 to hiring, but they just weren't our person for one reason or another.
 
So when I met Kelly Arndt, I knew I'd hit the jackpot.
 
🎰 He has a content background (WHAT?!) so he gets that story matters as much as performance.
🎰 He's a systems builder and a true believer in compounding incremental growth.
🎰 He has a bias toward action, a penchant for killer dashboards, and an experimental mindset.
🎰 He speaks fluent customer because he is the embodiment of our power users.
 
Kelly starts at Vector today (!!!) owning all things paid and growth. 
 
Six months felt like forever, but good people are always worth the wait.

Narrator: 𝘚𝘩𝘦 𝘴𝘩𝘰𝘶𝘭𝘥 𝘩𝘢𝘷𝘦 𝘸𝘰𝘳𝘳𝘪𝘦𝘥.
 

Here's what I didn't know was coming...

Josh posting "my head of marketing's on vacation, give me your worst ideas" and LinkedIn wholeheartedly accepting the challenge. Hundreds of suggestions. Everyone tagging me. Him hand-coding a website at midnight dedicated to his marketing crimes.
 
All while I'm in a pool in the Caribbean.
 
My mistake? 
Thinking he was joking when he dropped hints about "marketing plans" before I left.
 
His mistake? 
Not realizing I'd have WiFi.
 
The chaos that followed created the Josh & Jess dynamic that's still core to the Vector 👻 brand.
 
In the latest podcast episode of 𝗧𝗵𝗶𝘀 𝗠𝗲𝗲𝘁𝗶𝗻𝗴 𝗖𝗼𝘂𝗹𝗱'𝘃𝗲 𝗕𝗲𝗲𝗻 𝗮 𝗣𝗼𝗱𝗰𝗮𝘀𝘁, we break down:
→ How one joke post turned into one of our our biggest brand moments
→ Why Josh ended up shipping cards from his garage at $5 a pop (karma) 
→ The exact moment he realized marketing is harder than he thought 
→ How this accidental campaign shaped everything we do 
→ Why sometimes the best strategy is just trying something bold
 
People still ask if we planned it. The truth is I had no idea.
 
And somehow that made it perfect.

Raise your hand if you plan on updating your website content this year. 🙋‍♀️
 
(hint, your hand should be up)

The times, they are a-changing. There are SO many new way to get your content to work harder for you: feeding LLMs, creating buzz, handling objections, building trust, creating die-hard fans, and nurturing the 95% who aren't ready to buy just yet.

It's a LOT. 

But just breathe. Here's your first step. 👇
 
Get your ticket to 𝗔𝗯𝗼𝘃𝗲 𝘁𝗵𝗲 𝗙𝗼𝗹𝗱 — THE event for all things B2B websites — happening February 9–11 in Ft. Lauderdale, FL.
 
Two full days of workshops (hosted by the amazing peeps below) on the stuff that actually makes B2B websites work:
→ Brand
→ Positioning 
→ Messaging
→ Conversion optimization
 
And, of course, Content — hosted by me!

I'll walk you through Vector's content strategy, page structure, AI processes, and more, so you can see how we turn content consumption into dolla dolla billz.
 
Also, South FL in in February? Big ol' cherry on top.
 
If you are SERIOUS about coming, (like serious, serious) DM me for my half-off promo code.
 
See you in Florida? ☀️
https://lnkd.in/gvmqwBiF

The message testing strategy Josh 𝘥𝘦𝘧𝘪𝘯𝘪𝘵𝘦𝘭𝘺 knew about:
 

👉 Run a small ad campaign to test your positioning before launch day.
 
We launched a new product - Signal-Driven Ad Audiences - to see how people would respond to our new positioning, 𝘮𝘰𝘯𝘵𝘩𝘴 before everything else went live.
 
And instead of spending months workshopping it to death, we ran an ad campaign around it.
 
→ Real budget on the line
→ Real buyers seeing it (contact-level ad audiences FTW)
→ Real engagement (or crickets)
 
The fastest way to see if messaging resonates with actual humans.
 
I know for a FACT I told Josh about this beforehand, though he claims otherwise. He literally approved the creative. 😆
(In his defense, he was probably thinking about 47 other things.)
 
But I digress...

Your ad campaigns can do double duty. They're not just for demand gen—they're also your fastest feedback loop on whether your message and offer actually land.

Joshua Perk 👻 and I dig into all things ads at Vector 👻 in the latest episode of 𝗧𝗵𝗶𝘀 𝗠𝗲𝗲𝘁𝗶𝗻𝗴 𝗖𝗼𝘂𝗹𝗱'𝘃𝗲 𝗕𝗲𝗲𝗻 𝗮 𝗣𝗼𝗱𝗰𝗮𝘀𝘁 - out now!
 
AND if you dig what we're putting down, we're doing a LIVE episode next week. 😬 There's no telling what could happen. Get a front row seat with the link in the comments.

What's one of your Q1 marketing bets that's making you nervous?

Here's mine. 👇
 
Joshua Perk 👻 and I are recording a LIVE episode of 𝗧𝗵𝗶𝘀 𝗠𝗲𝗲𝘁𝗶𝗻𝗴 𝗖𝗼𝘂𝗹𝗱'𝘃𝗲 𝗕𝗲𝗲𝗻 𝗮 𝗣𝗼𝗱𝗰𝗮𝘀𝘁 this Wednesday, January 14, at 12 pm ET.
 
No editing. No do-overs. Just us, talking through our entire 2026 marketing plan in real time.

We'll share:
→ The market forces that shaped our plan
→ Our 3 "big rocks" for the year
→ The channels we're putting most of our dolla billz into
→ Sneak peeks of our hiring, event, and influencer plans
→ How we'll know if any of this (gestures around wildly) is actually working
 
All delivered with our general weirdness... and nowhere to hide.
 
See you there?! 🤞
https://lnkd.in/g8GDaSw8

Hey, real quick...
 
Josh and I are doing a LIVE episode of the podcast in T minus 3ish hours—sharing Vector's entire marketing plan for 2026: big rocks, goals, hiring, the whole shebang.
 
Would love for you to be a part of it if you're free at 12 noon ET. (And if you're not, register anyway so you get the recording!)

Hope you can make it! https://lnkd.in/g8GDaSw8

Jess and Josh from Vector standing against a blue background with pink and yellow geometric shapes. Text reads 'This Kickoff Could've Been a Podcast LIVE! with event details 'Jan 14 @ 12pm ET' and 'TODAY!' on sticky notes. Vector logo and ghost mascot appear in bottom right corner.

I already have seven conferences lined up on my calendar this year. 😳

Some we're sponsoring.
Some we're going to see and be seen.

But the one I KNOW is going to level up my skills (and confidence) as a newly minted VP of Marketing?

The Exit Five Marketing Leadership Retreat
🌵 March 18-20 in Paradise Valley, AZ

A two-day working session with people who've been running marketing for years and can help me answer some of the questions I'm wrestling with right now:

• How do we keep our brand narrative focused as our team grows?
• What are the next key hires that will continue to propel our growth? 
• How should we adapt if we're not hitting our goals?
• How do we outdo what we did last year?
 
The group is small. The conversations are real. And there's nothing like learning from people who've already made the mistakes you're about to make.
 
There are only 100 spots and it's already half full. So, if you're new to leadership, a seasoned pro, or just want to pressure-test your thinking with other marketing leaders, come join me.
 
Details here:

Open article: Marketing Leadership Retreat | March 18-20, 2026 by bit.ly

Marketing Leadership Retreat | March 18-20, 2026

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

"We just need better messaging."

Actually, you need better positioning.

Positioning always comes first.

Here's the down low: Companies hire a copywriter to fix their website. And a copywriter often rewrites everything beautifully. Professional. Polished.

But you need a foundation before you create demand. You can't write your way out of unclear positioning.

Messaging is how you say it. Positioning is what you say.

If you don't know who you are for and what makes you different, no amount of copy will save you.

It's like asking someone to wrap a gift when you haven't decided what's inside the box.

B2B Healthcare SaaS Positioning & Messaging | ☕️ Espresso connoisseur

Happy to share that I'm drinking more coffee in 2026.

Please join me in this celebration.

"It's crazy how fast AI is replacing copywriters and marketers."

...is what I typically say when talking to copywriters and marketers.

Really frees up the job market for me.

Last year was a wonky year for me.

It was my best year in some ways, but also a year of endless headbanging against walls (still doing a bit of it right now).

For nearly 10 years, I've done all things copywriting. And gotten pretty dang good at it (so my kids tell me when they see a YouTube ad that they think I wrote).

But last year, I pivoted even more into the realm of B2B positioning.

I tested new offers like a madman constantly tweaking the perfect cup of espresso. 

I leaned into it. Failed. Leaned into it a bit more. And failed a bit more. And more and more (until I drank my sorrows away with more espresso).

And that's why I'm leaning more into B2B positioning. 

I know, weird.

Because the handful of amazing clients I worked with this year were absolutely amazing. Sure, I got hundreds of "no's, go away, and wrong person."

But that's part of building a solo consultancy. 

The best basketball players make 40% on 3s. The best baseball players hit a pitch 3 out of 10 attempts.

Rejection is part of the game. Falling on your face is part of the game. Even losing is a part of the game.

Giving up is not part of the game.

B2B healthcare SaaS positioning | ☕️ Espresso connoisseur

Bienenstich or bee sting cake. 

Divinely delicious. Will be making this again and again and again.

No alternative text description for this image

Your homepage or landing page hero section is your three-second argument.

I like to think of it as: 

- What's compelling to the readers? 
- Is your headline, subheadline, and proof all compounding to what matters? 
- And does the reader have confirmation that your promise actually works?

Positioning steers all of this.
 
Good copywriting follows good positioning.
 
Every headline sounds good until you realize that the product you're writing copy around has zero positioning strategy.

When a B2B product has a clear roadmap, the messaging has a roadmap, and the copywriting has a roadmap. 

Everyone has a roadmap. 

Even more importantly, your customers have a roadmap of how to see your product.

Made sponge cream cake (Erdbeerrolle), so I have the right food supplies during this ice storm.

Didn't really turn into a roll. But it was still delicious.

Stay safe out there!

There are those who get in shape at the beginning of a new year. 

And there are those who double down on making pie and cheesecake.

Starting the year off strong 💪

B2B Healthcare SaaS Positioning | From Decks to Email Messaging | ☕️ Espresso connoisseur

B2B healthcare startups should avoid overhyped messaging.

Stop overpromising outcomes on a new feature. Stop talking about how excited your company is to launch that product.

Your customers don't care about super overhyped messages:

"We're launching our biggest product yet"
"Our product will change your life"
"Our product will save you hundreds of hours!"

You throw believability out the window with overhyped products that your audience knows nothing about.

Your audience wants two things:

1: Clarity of what your product is
2: How it's different

And the more you can tie it to a problem (and the conversation inside your buyer's head), the more believable it is.

Because nothing matters if you don't understand the problem you're solving.

Nothing matters if you don't understand how your buyers think and feel about their current problem and what's pushing them to a new solution.

Your buyers need a frame of reference. They need certainty. And they want frictionless clarity on what you do.

Easily one of the best flowcharts ever made.

Saying you can tell a story through email is like saying you can bake a cake.

Sure, you can make it but it doesn't mean it's gonna taste absolutely scrumpiously amazingly divine. 

And therein lies the magic of copywriting.

We know there are templates. And there's AI. And there are folks who don't use either and probably should.

Writing good emails about B2B products is never about writing about B2B products.

It's about knowing your reader's frame of mind, how they think and feel about your product (the pain they desperately hate being in).

And making them more aware of what your product can do for them. Not just by listing feature after feature.

But by painting a picture for them.

The last few months, I had the amazing opportunity to work with Britt Prim and Karias Health.
 
And they were the absolute best!

Loved helping them with all things positioning, messaging, and getting their prospecting emails dialed in (and talking all things Stranger Things with Britt).
 
And I love even more that they booked multiple meetings (and pipeline activity!) from these emails.
 
Nothing better helping healthcare teams win!

Britt Prim thanks for being awesome, kind, and an absolute joy to work with!

11 signs you need to fix your B2B healthcare positioning:

1. Your story is built around product features, not market change.

2. Your competitive analysis only lists competitors, not the status quo being replaced.

3. Your prospect refills their coffee cup 3x before you finish your pitch deck

4. Your differentiation sounds amazing internally but never actually show clear buyer value 

5. Your positioning deck is built for multiple buyer personas in a single sentence

6. You think you're about to own market category and you started your company 6 months ago and have three customers

7. You're testing messaging with your team instead of actual ICP prospects before launch (skipping voice of customer validation)

8. Your homepage headline, deck, and emails describe three different products and solutions you're solving

9. You see your competitors win because they're positioned in a clearer category 

10. Your prospects (maybe) forward your cold email asking "do we already have this?"

11. Your pitch deck has more words and images on a single slide than your 3-year-old's drawing.

The hardest thing about pitch decks is getting them to lead the messaging of your emails and landing pages. 

The problem is taking a deck (written in your voice) and turning it into an asset (written in your customer's voice).

Your deck is the problem you're solving and how you differentiate yourself in the market. You have to tell that story through the lens of your buyers.

The challenge is knowing your reader's awareness.

You have to know what conversation is happening in their heads (hint: it can't be a big problem you think it is)

Even more importantly, you have to take the logical langugae of your pitch deck and turn it into emotional copy.

Positioning creates internal alignment across the board.

Great copy shows up when your team has a clear position, understands where your buyers are in their story, and knows how to turn that into words that win people over.

The worst advice on hero sections is:

"Just make it clearer"

Something that's clear to an engineer could be wildly unclear to a clinical director. 

And it's only bad if you don't know how to make it clearer. The HOW of how to make it clear.

First, you need to know the 4 types of readers (h/t to Joanna Wiebe for this):

- Spontaneous (fast, emotional) They are the skimmers that want to know “What is this?” and “What can I do here?”

- Competitive (fast, logical): They are scanning for “What is this?” + “Who is it for?”

- Humanistic (slow, emotional): They like to read the whole page, but feel uncertain if they don't know what the hero section communicates

- Methodical (slow, logical) They notice the hero, but treat as a map for directions

And what they all have in common is these want these questions answered (and 8 seconds or less):

- What is this? 
- Who is it for?
- What can I do here?

Especially in B2B healthcare SaaS, when you have to be clearer than ever who your champion is and how you're helping them (and what category you're competing in).

It's easy to sound good internally. But does it make sense to your buyers?

P.S. I share more copywriting (and positioning) examples in my newsletter every week: https://lnkd.in/emV7YTJP

Love working with the Promptly team!

They are doing amazing things in healthcare, especially around specialty practices. Like seriously amazing.

And they have an awesome amazing team behind it all. I had a blast working with them on positioning strategy to messaging. 

P.S. If you're a B2B healthcare company and need help with positioning and messaging, I have a few spots for my positioning accelerator in February!

Don't sign up for my newsletter.

Unless you like espresso, B2B healthcare, copywriting techniques, positioning decks, and that's about it.

Then definitely sign up for it. 

Here's what I'm sending out today in my newsletter (one of three examples) that I'll be explaining.

P.S. Here's the link if you want to give it a looksie - https://lnkd.in/emV7YTJP

I talked to a B2B healthcare startup last year that had two positioning problems:

1. Differentiation doesn't show up in messaging (especially around AI products)
2. Closed / lost calls showed that buyers didn't see the urgency to act

In essence, their product “does AI for healthcare” with almost endless use cases.

It was difficult to identify a champion. And it's difficult for champions to accept change when there's urgency to change.

All in all, there are two things you have to remember about B2B healthcare positioning:

Put your product in a clear differentiated box and make the cost of staying with the status quo feel higher than the cost of changing.

If you're in B2B healthcare, you have a huge positioning opportunity.

The launch of ChatGPT and Claude Health shows how they are positioned around accessibility.

The mistake would be to chase the same positioning narrative:

- The most accessible AI for healthcare professionals
- Your personal AI assistant for health records
- Making AI healthcare simple

These are broad, vague, and you're competing in a category that never gives you a chance to win.

To stand out, you need to identify:

- Your champion (who cares the most)
- Define the alternatives (what did your champion use before you)
- Anchor into a problem
- How your differentiation solves that problem
- How that's framed around the market
- Take that frame and built out voice of market messaging

The mistake is that B2B healthcare startups will choose competitors (that aren't really competitors) and call out how they are different.

The mistake is picking the wrong competitor (like ChatGPT). And not listening to what your buyers really care about.

It's about going narrow and not trying to own a category that you're not really competing in to avoid category confusion.

Choose a roadmap that allows you to win over and over.

Abridge is a good example of this:

Narrow positioning: "Leading healthcare AI infrastructure powering the most trusted clinically useful, billable, and compliant notes at the point of care."

(If) they chose poor positioning: "The most accessible AI assistant for healthcare professionals"

Abridge chose a positioning that made them the obvious choice for clinical documentation.

As a B2B healthcare startup, your reaction shouldn't be, "Oh no, we can't own healthcare accessibility anymore."

Your job was never to own it. Because your startup had no business being in that category.

Show your customers, teach them, why your B2B healthcare's strengths are perfect for specific niche markets.

Most positioning fails because it doesn't go anywhere.

It stays hidden in a deck without ever traveling into the world of landing pages and emails.

Positioning is the story you tell to align your entire team. And it's the story that you express in your emails and landing pages to your buyers.

Why emails and landing pages?

1. Emails are a sequence of telling that story
2. Landing pages allow you to focus on one problem, one reader, and one promise

Positioning gives your product context. And that context has to be communicated clearly.

Positioning isn't a standstill deck. It should travel internally to align your team and externally to tell a story to your buyers.

taplio

The Battle

Jess Cook

Benjamin Watkins

Followers

Posts

Engagements

Likes

Performance ScoreJess Cook's LinkedIn Performance

Performance ScoreBenjamin Watkins's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Jess Cook

Benjamin Watkins

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jess Cook's LinkedIn Performance

Performance ScoreBenjamin Watkins's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreJess Cook's LinkedIn Performance