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.

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

Never underestimate this as a LinkedIn strategy.

B2B Healthcare SaaS Positioning & GTM 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.

B2B Healthcare Positioning & Messaging | ☕️ Espresso connoisseur

A fundamental difference between good and bad copywriting comes down to pronouns (me vs. you).

Bad copywriting (all about me):

• Check out my product
• Check out what my product does
• Check out why my product is awesome

Good copywriting (all about you):

• You have a problem
• You are looking for this benefit to solve it
• You are looking for a product that has these benefits and solves your problem

Always make it about the customer.

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

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.

Change your perspective, and you change your outlook on life!

Also, nothing beats Calvin and Hobbes.

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.

"When is a B2B company ready for positioning work?"

B2B healthcare startups ask me this a lot. Positioning is nerve-wrackinig if you don't have the data, or the customers. 

On the flip side, it's even more stressful when you're growing like crazy, but there's no real clarity around your positioning.

They both have something in common: You need to make the decision nobody's made yet.

Positioning is ultimately about pattern recognition. Can you name who you win? Do you know why you win them? Can you describe what they were doing before they found you?

That kind of clarity doesn't come before the work. It comes from the work.

What I tell founders is that picking a segment is a sequencing decision, not a forever decision.

And as the market changes, you have to revisit your positioning. 

The healthcare companies that struggle aren't the ones that position too early or too late. It's avoiding a decision altogether that impacts how your team sees you and (even more important) how your customers see you.

Everyone should follow and learn from Darren.

The best of the best when it comes to LinkedIn. I learned every single thing I know about LinkedIn and social selling from this dude.

LinkedIn & Social Selling took me from the mailroom to the boardroom in 10 years | Founder of Darren McKee Co. & 531 Social

Been a wild 4-5 weeks. 

I’m tired but it’s hard to even say that because I dreamed, hustled and prayed to eventually have days like these.

Now it’s happening. 

Time to rest, recover and ge the work life pendulum back in line.

Where do I start winning → Why do I win there → How do I say that

Or think of it like this: 

Wedge → Positioning → Messaging

Your wedge is the strategic choice that makes positioning possible. Especially if buyers don't know who you are.

Now, if you're in a known category, competing head to head, and buyers know what they are looking for, then you don't need a wedge.

My 8-year-old son likes to ask me when we're going to get a new car.

Even though our 2019 Honda Odyssey works perfectly fine.

I try to tell him that new does not equal better. You don't need the newest thing especially when the old thing isn't broken. 

I don't have a sense of urgency to get a new car. I don't want to spend money on something I don't need. And what I have works perfectly fine.

And that's a lot of the problem around AI.

Don't get me wrong, I love testing out new AI tools and projects.

But when you're trying to sell an AI product, you're not selling something brand new. Because nobody sees a need for that, no matter how cool it is.

You're showing the cost of something broken. You're showing the pain. You're walking them through the feeling of something that doesn't work.

A lot of AI tools, especially in healthcare, have to show that.

Otherwise, it's just something that's new. It's making an announcement where nobody cares what you have to say.  

Just because it's new doesn't mean it's useful.

Just because you can release an AI product, doesn't mean you should unless you're actually solving a tried and true customer pain.

I'll also be keeping my honda odyssey for a good while.

Nobody ever bought B2B healthcare software because of a "unified real-time platform." 

They bought it because something was broken and they were tired of pretending it wasn't. 

They care about the thing that's broken today. So that's where you start. You position around the pain they already feel. You use their words, not yours. 

But you don't stop there.

Once they see themselves in your positioning, you shift the story. You explain why that pain keeps showing up. 

The old game was built on manual processes and lagging indicators. The new game requires real-time data and proactive intervention. You're not selling yet. You're changing how they see the problem.

And then the sales conversation becomes easy. Because you're not convincing them they have a problem. You already did that on the homepage. You're not reframing their world. You already did that in your content. 

Now you're just showing them why your approach is the one that actually solves it.

Three steps. And each one earns the next. And the messaging at each step sounds completely different.

Most B2B healthcare companies try to do all three in one homepage headline. And that's why it reads like "Empowering organizations to deliver better outcomes through innovative solutions."

Which could be about a hospital. Or maybe even a really good sandwich shop.

Stop thinking of your B2B product as horizontal vs. vertical. Because it doesn't matter.

You need to first think about how it's positioned.

B2B companies get stuck on the entire strategy of horizontal or vertical, and then let it become their positioning. 

For example, the horizontal company says, "We're the #1 CRM, now for healthcare." 

The vertical company says, "We're built exclusively for healthcare." 

And yet, both are describing what they built. And neither is telling the buyer why it matters to them.

Take Clarify Health. They built a horizontal concept around data analytics. 

❌ They didn't say "we're a cloud analytics platform for healthcare."

Instead, they found the context that made their value obvious (healthcare executives are making billion-dollar care decisions with gut feel). 

✅ They gave it context: "Moneyball for healthcare".

CarePort Health is an example of going vertical. 

❌ They didn't say "we're a vertical discharge platform." 

✅ They named the pain no one had solved: "Nurses calling facilities, one by one, to place a patient."

Remember, horizontal or vertical can win. 

You'll never win by leading with what you built instead of the value it creates for the buyers who care most.

Find the context that makes your value obvious.

Drinking more coffee and sharing more positioning truths.

I work with B2B healthcare startups on positioning and always notice these challenges.

1) Competitors are often assumed rather than hearing what your market tells you. Listen to your market when they compare to the alternative.

2) Your market has a problem. They have a belief around that problem and the context that surrounds that problem. Listen first before inserting your product into the conversation

3) Everyone promises better patient outcomes. Better healthcare. Better everything. But what is something unique in value that you deliver that comes from your capabilities? That's where you stand out.

That's all for today's lesson.

Positioning is about knowing which game you're playing.

The mistake I see from B2B healthcare companies is borrowing the playbook from a quadrant they don't belong in.

Here's how it breaks down. 

Two angles: how broad your solution is (point solution vs. platform) and how healthcare-specific it is (generic infrastructure vs. built-for-healthcare).

Here's what confuses everyone. 

These aren't stages. You don't "graduate" or jump from point solution to platform. Each one is its own game with its own way to win and its own way to lose. And a level of education you have to do.

Positioning failures happen when a healthcare point solution tries to position like a platform. 

Don't put yourself in a positioning game you're not even supposed to be playing in.

Put yourself in a positioning game where you have the highest opportunity to win.

B2B healthcare is wild in 2026.

Every B2B healthcare startup wants to know how to "position their AI." AND it's 1000% the wrong question.

The right questions were before AI showed up.

1) What game are you playing?  
2) Why should the buyer care?

April Dunford has been saying this for years. Positioning isn't about describing what your product does. It's about defining the context that makes what you do make sense. 

The category, the competitive alternatives, and the value you deliver that nobody else can. 

That framework didn't retire when ChatGPT arrived. If anything, it's now even more important because now every company sounds the same.

And that's the part nobody's talking about. The AI wave didn't create a positioning problem. 

It exposed the one that was already there. 

The B2B healthcare SaaS startups winning right now aren't the ones with the best AI. They're the ones who can explain why their AI matters to a specific buyer with a specific problem in a way that nobody else can. 

That's a positioning advantage (not a technology advantage).

Went down a rabbit trail around how espresso was made.

And it led me to positioning. So, espresso is positioning. Imagine that. 

That means drink more espresso.

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