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

Marketers can spot lazy creative from a mile away.

We roll our eyes at generic messaging. 

And we definitely know when someone's trying too hard.

But we also know when something's genuinely different. 
When a brand is doing something we haven't seen before. 
When the execution makes us stop scrolling and think, "Okay, that's actually clever."

That's the bar I want Vector 👻 to clear.

And with that, I give you "Warm Water, Warmer Leads."

We had 20 seats at our Exit Five Drive dinner.
 
And the way we filled them is different than what you'd expect.
 
Here's how we did it ⤵
 
Exit Five sent us an anonymized attendee list.
 
Just title, company, industry, and URL. No names.
 
So I passed it to our Rev Ops lead, Sara McNamara, and asked her to work her usual enrichment magic.
 
What she handed back was insane: 
→ Full names and LinkedIn URLs 
→ Their martech stack 
→ Number of ads currently running on LinkedIn
 
From there, I filtered ruthlessly:
 
✂️ Anyone running below a certain ad threshold (probably not our ICP) 
✂️ Small companies without the right team structure for our tool 
✂️ Anyone who wasn't a decision-maker or close to one
 
I needed people who could either make a buying decision or bring Vector 👻  directly to someone who could.
 
Then, I filled the other half of the seats with customers.
 
Joshua Perk 👻 was all, "Jess, we already sold them. What's the point?"
 
But because we seated them strategically next to prospects, we (the Vector team) didn't pitch Vector once that night.
 
We didn't have to.
 
Our customers did it for us—naturally, authentically, in their own words.
 
I'd walk around the restaurant and just... listen:
 
"Here's how we're using it..." 
"We've built our entire workflow around it..." 
"The results have been incredible..."
 
Way more powerful than anything we could've scripted.
 
Plus, it allowed our team to truly get to know our guests. We talked about our kids, our current Netflix obsessions, our favorite places to travel. All of which made follow up and opp creation a heck of a lot easier.
 
Josh and I break down our entire event sponsorship debut in the latest episode of This Meeting Could've Been a Podcast—out now!

• Why we selected the events we sponsored
• How we crafted an on-brand experience
• Our event plans for 2026
• The story of the three-hour scramble when the dinner got moved up a day

You know where to find the links! 👇

Hey, what are you doing Dec. 9-10?

Cuz it'd be cool or whatever if you could go to Full Circle with me.

It's for small, B2B marketing teams with big ambitions. Which, is like, totally us.

I made you a mix tape about it. ☺️

Wanna go?

☐ Yes (I left you a link in the comments.)
☐ No (Forget I said anything. Pretend this never happened.)

Full Circle Mixtape Vol. 2

Lead magnets have their place.

But this year, we focused squarely on awareness magnets.
 
And our podcast is proving it works.
 
→ More shared and talked about than 90% of shows on Spotify
→ Branded search up 430%
→ Inbound demos from people who "saw us everywhere"
 
They come in pre-sold on our vibe. Pre-educated on our POV. Pre-convinced we're the team they want to work with.
 
Meanwhile, our competitors are still gating their best ideas behind forms with very little investment toward getting people to CARE about them.
 
Sure that's harder to measure, takes longer to pay off, and requires way more creativity. 

But being forgotten is more expensive than all of that combined.

Because you can't convert people who don't know you exist.

------------------------

So proud of our little show that turned into a big show. Go check out This Meeting Could've Been a Podcast if you haven't already!

#SpotifyWrapped

When you pivot your entire company, your marketing goals have to pivot too.


We spent months repositioning Vector: new messaging, new pricing, new website, new everything.

Which meant we also have to temporarily shift from "will we hit our revenue number?"
to "is this pivot even the right direction?"

𝗠𝘆 𝗷𝗼𝗯 𝗯𝗲𝗰𝗮𝗺𝗲: 𝗳𝗶𝗻𝗱 𝘁𝗵𝗲 𝗹𝗲𝗮𝗱𝗶𝗻𝗴 𝗶𝗻𝗱𝗶𝗰𝗮𝘁𝗼𝗿𝘀 𝘁𝗵𝗮𝘁 𝗽𝗿𝗼𝘃𝗲 (𝗼𝗿 𝗱𝗶𝘀𝗽𝗿𝗼𝘃𝗲) 𝘁𝗵𝗶𝘀 𝘄𝗮𝘀 𝘁𝗵𝗲 𝗿𝗶𝗴𝗵𝘁 𝗺𝗼𝘃𝗲.

I landed on three goals.

1️⃣ 𝗛𝗼𝗺𝗲𝗽𝗮𝗴𝗲 𝘁𝗼 𝗱𝗲𝗺𝗼 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗶𝗼𝗻 𝗿𝗮𝘁𝗲 
(Peep the video to see where you want it to be.) 😁

2️⃣ 𝗜𝗻𝗰𝗿𝗲𝗮𝘀𝗲 𝗱𝗲𝗺𝗼𝘀 𝗯𝗼𝗼𝗸𝗲𝗱 𝗯𝘆 𝗜𝗖𝗣 𝗽𝗲𝗿𝘀𝗼𝗻𝗮𝘀 𝗯𝘆 𝟱𝟬% 

3️⃣ 𝗗𝗲𝗰𝗿𝗲𝗮𝘀𝗲 𝗱𝗲𝗺𝗼𝘀 𝗯𝗼𝗼𝗸𝗲𝗱 𝗯𝘆 𝘀𝗮𝗹𝗲𝘀 𝗽𝗲𝗿𝘀𝗼𝗻𝗮𝘀 𝗯𝘆 𝟱𝟬%

Because positioning has to do TWO things at once: attract the right people AND repel the wrong ones.

We're nearly a month past launch, and we're nailing these goals.

But this taught me something valuable about pivots: You can't just keep measuring what you measured before.

Get the full scoop on how we pivoted Vector without breaking the business (and ourselves) in the latest episode of This Meeting Could've Been a Podcast—out now!

If you're spending $25k+ per month on LinkedIn ads, this is your BOGO moment.
 
No promo code needed.
 
Vector's new Bid Agent just launched, and it's basically Black Friday for your ad budget.
 
Flip a switch and start getting 25-60% more outcomes for the same spend.
 
𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝗶𝘁 𝗱𝗼𝗲𝘀:
 
LinkedIn's Max Delivery is designed to win auctions. Not to maximize what you get for your money.
 
Bid Agent adjusts your bids every 15 minutes to find lower-cost windows and higher-density impression periods within your audience.
 
Same targeting. Same people. Way more outcomes per dollar.
 
"𝗪𝗮𝗶𝘁, 𝗰𝗵𝗲𝗮𝗽𝗲𝗿 𝗰𝗹𝗶𝗰𝗸𝘀 = 𝘄𝗼𝗿𝘀𝗲 𝗾𝘂𝗮𝗹𝗶𝘁𝘆 𝘁𝗵𝗼𝘂𝗴𝗵, 𝗿𝗶𝗴𝗵𝘁?"
 
Nope.
 
LinkedIn still only shows your ads to the exact audience you define. Bid Agent just finds the moments when reaching them costs less.
 
(And things get REAL interesting when you layer it on top of your contact-level audiences built in Vector.)
 
If you're a demand gen leader that has this kind of buying power on your wish list, there's a link in the comments just for you.

It snowed here this week. So I need very little convincing.

But if you're someone who needs a bit more to go on...

Here's your sign to join me at Above the Fold in February. Two days of workshops focused on one thing—B2B websites—in Ft. Lauderdale, FL.

In my mind, I'm already there. 😎

See you in FL?

Benjamin Watkins

Watkins Agency

Watkins Agency is a positioning and messaging consultancy for B2B healthcare brands.

We've worked with Tomorrow Health, Focus Solutions, Sycle, Validic, Laguna, SingleComm, Penelope, Anya Health, Ayin Health, SmartCue, DexCare, and Parallel.

Founder of Watkins Agency

This Is Copy

This Is Copy is a resource to help copywriters and marketers in healthcare.

From workshops to content, we show founders, copywriters, and marketers how to speed up sales cycles, reframe sales emails, and create persuasive messaging.

Founder of This Is Copy

La Vie Ben Rose

Every week, I share copywriting examples and columns in B2B healthcare and SaaS.

I share email and landing page messaging techniques. I also look at data-driven strategies that help brands capture the voice of the customer to improve conversions and shorten sales cycles.

I've had the privilege of working with brands like BristleHealth, Tomorrow Health, Telemedicx, Sycle, Penelope Retirement, EverTransit, Anya Health, Laguna Health, Lucinetic, SingleComm, Parallel Learning, SmartCue, and more.

Founder

I teach creators, brands, copywriters, and marketers all about copywriting, writing, and creativity through cohorts, workshops, and courses.

I also like to write about what I'm learning until my brain needs more coffee.

Writer

California State University, Monterey Bay

Guest speaker at CSU Monterey. I help students and entrepreneurs with copywriting, marketing, and communications strategy.

Guest Speaker

RXMG

As Content Coordinator, I am responsible for writing and developing high-quality copy (clear, concise, and grammatically correct) for digital marketing campaigns and internal sites across all verticals; monitor effectiveness of marketing campaigns and align content creation with audience engagement trends; to coordinate between internal departments/teams and external advertisers and affiliates to ensure all content requirements are being met and relaying performance and; to develop and maintain systems and processes for managing copy and measuring performance. 

Other responsibilities include understanding the different language styles that appeal to various audiences/industries; being highly creative and curious about client's products, services, and industries; editing copy for message clarity, flow, consistency, grammar, brand voice, and tone; the ability to work autonomously on content assignments, often with tight deadlines and; regularly communicate with internal and external parties and maintain a high level of relationship management and confidentiality.

Email Coordinator and Lead Copywriter

NORCAL Ambulance

BLS emergency medical technician for hospitals and skilled nursing facilities.

Emergency Medical Technician

Ripon Unified School District

8th grade self-contained class. Teacher of History, Science, English, and Math.

Teacher

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)

Watkins Agency is a consulting firm that helps B2B healthcare & tech companies with positioning and messaging.

We get your customers to say, "This is a no-brainer," so they buy faster and understand everything you do.

And we do that by clarifying your positioning, sharpening your messaging, and writing compelling, voice of customer snazzy copy.

Loved by Tomorrow Health, Bristle Health, Focus Health, Sycle, Validic, and DexCare.

We've also:

→  I've helped SmartCue rank no. 1 on ProductHunt
→  I've worked with Bristle Health to align positioning and messaging
→  Helped Tomorrow Health get clear on positioning and messaging to elevate their sales deck
→ Developed Sycle's messaging around lifecycle emails

"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! Not only did he turn around awesome copy but he went out of his way to help us get things right before launch! Hire Ben! 💯"

- Robin Singhvi, Founder of SmartCue

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

www.ThisIsCopy.com

People sometimes ask me, "Ben, how do you find time to write with 5 kids at home?"

I actually have a simple strategy for that.

It's called, "Hiding"

I hide in the garage. I hide in the bathroom. I hide behind doors. I hide behind curtains. I hide on the roof.

I didn't even realize how many hiding spots were in my house until I worked from home. And there are a lot.

It even sparks spontaneous conversations when I hop on zoom calls with prospects and clients.

"Where are you working, Ben?"

"Oh this? It's just the top of the roof."

And that folks, is the secret to working from home.

Positioning & Messaging for B2B Healthcare SaaS. Deeply researched positioning insights (while I make more coffee)

Waiting for LinkedIn to send out this notification:

"Since OpenAI is down, you may see LinkedIn posts riddled with spelling errors, fewer hyphens, and that seem like an actual human wrote them (I know, a bit bonkers).

Do not be afraid, the robots will eventually return."

Positioning & Messaging for B2B healthcare & SaaS. Deeply researched positioning insights (while I make more coffee)

If you're ever stuck in your copywriting process, just ask these questions

1: Who's the enemy of what I'm trying to say
2: What's the conflict
3: What's the ultimate truth I'm trying to get at

Things are more interesting when you're finding the conflict in things. 

And it makes it more interesting to read.

One of the coolest and most underrated LinkedIn features that LinkedIn doesn't even tell you about is the ability to see someone's post from 3 weeks ago.

It's like forcing someone to time travel back through LinkedIn time regardless if you want to or not.

"The older I get, the more I realize self-confidence makes all the difference."

I remember seeing this tweet from Justin Welsh. And it made a huge difference in how I do business.

2025 was about having the confidence to get rejected as much as it was to test new offers. It was about putting myself out there regardless of the outcome.

The biggest highlights in 2025 were:

- Doing so much more positioning work for B2B healthcare
- Getting better at outbound, especially on LinkedIn
- Having the confidence to launch a new positioning offer
- Actually buckling down and implementing systems (and sticking with them)

I also worked with the awesome Darren McKee and Ken Yarmosh on all things sales, LinkedIn, and actually building a solo business with the right systems and processes.

I've also doubled down on connecting with healthcare folks in Slack groups like Health Tech Nerds. 

While I adopted a lot of things into my business, I actually decided to delete email from my phone, and it's been a game-changer. I was checking it every 5 minutes.

I have to remind myself that the business I'm building means to give myself grace whenever I'm stuck or not going as fast as possible.

I get a lot of opportunities that I actually need to take more advantage of, even if it means slowing down. The world won't end. It means random 2 pm bike rides with the kids, rewatching Stranger Things at lunch break, or just pausing to slow down for a minute.

I get to work with awesome clients. I get to build a business that affords me so many opportunities. 

2026 is about building that confidence, doing more positioning workshops with emails and landing pages that showcase it, going to an in-person conference, and meeting more awesome people (while drinking more coffee and eating more toffee).

If you want to work together on your brand's positioning (especially around decks, emails, and landing pages), shoot me a DM!

P.S. Thanks Jason Faber for the inspiration!

2025 Wrapped

Here's a brushup:

Positioning is what you’re allowed to say 
Messaging is how you say it. 
Copywriting is where and in what words you say it

Memorize. Pop quiz in 2026.

Is positioning in B2B healthcare actually harder?

In some instances, yes, because you're often dealing with more risk, more decision makers, and you're always challenging the status quo.

So you're creating alighment across teams in a sales deck and across your emails and landing pages.

The challenge is two fold:

First, you have to first get super clear on your positioning.

1. Map out the reason why customers choose you
2. Know your differentiated value
3. What jobs to be done are you solving
4. What are the unique (provable) attributes you are winning in the market
5. Identify your champion who care the most about your specific value 

Then you have to get your positioning something to stand on with your messaging.

1. You've built a clear differentiated story
2. You've mapped out attributes your customers care most about
3. You've clearly identified your champion that you can call out in your messaging
4. You know what problem you're solving (and the use case you can say in your messaging)
5. Choose the category that reiterates the voice of the customer and what they believe

In B2B healthcare, the solutions have to be more obvious because there are more decision makers and they need 

Whenever I work with healthcare teams, we go through this process and we uncover these central questions:

1: Who are we the best for?
2. Why would they switch?

Of course, there are a lot of reasons you want to find out around these. But the point is to find multilple directions.

P.S. Here's a before/after that shows what happens when you know who you're best for and why they'd switch

I don't usually give a shoutout to startups, but gotta hand it to Maggi Heneghan and Sumly.

Beyond being super kind, helpful, and knowing everything about taxes (the season I hate most), they have an app that's insanely good for solopreneurs like myself.

Been using their app for all things business and it's been amazing (no affiliation or anything). Better than QB. Better than anything I've tried.

They keep doing awesome work. And everyone should try them (if you're a solopreneur that is).

Superlatives don't belong in your copy.

Across all of the landing pages and emails I've written, I've learned that it really creates three kinds of problems:

1. It's not voice of customer
2. If a customer said something of the sorts, it's usually taken out of context
3. Superlatives are a shortcut to writing lazy copy because you want your product to sound amazing

A simple fix is to replace all of your superlatives with specifics.

You can actually work backwards like this.

1. Give your headline a superlative
2. Ask your product, sales, and marketing team why they think it's the greatest
3. Compare it with why customers say the product is so good or what it helps them achieve

You have to systematically break down why your product is so great.

Because hype does not equal persuasion.

In my experience, there's always a disconnect between telling someone how great your product is vs. showing them

Your team wants to hype up the product. Your team wants to impress by throwing in superlatives (and it actually causes skepticism)

Your product doesn't sell more on the hype you give it.

Your product will sell more based on the hype your customers give it.

The most valuable lesson I've learned as a B2B healthcare positioning consultant?

Positioning is wildly misunderstood.

There's a lot of whack-a-doo positioning nonsense out there about how positioning is just a marketing exercise. Or it's just something that lives in our sales deck.

I hear it a lot across B2B healthcare:

- We have multiple products and don't have a flagship product
- We have lots of differentiation, but don't know which one to lead with
- Our positioning needs revisiting because we've changed since we talked about it

It all boils down to knowing how to stand out in the market.

It's easy to say why you're the best, why you're the best, and yada yada yada.

The hardest thing about positioning is saying who you're NOT for. It's choosing a direction based on what your customers value the most (not what you like or gravitate toward the most).

And that means staying out of your own way.

Because when the positioning is done right, it shows up on your website, landing pages, and emails.

Was going to write a banger post on B2B healthcare positioning. 

Got distracted and made bread instead.

No alternative text description for this image

B2B healthcare emails are still wildly underused (and undervalued).

Most B2B emails in general are webinars, updates, or "see you at the next conference" emails.

There's a real lack of emails that drive storytelling, take readers from unaware to problem aware, segment, or even highlight a real and relevant problem.

A core positioning narrative fixes a lot of this (if you can take it from your deck to your emails).

That means your nurture emails know how to frame a problem. Your outbound emails have a strong POV. Your product emails read like real value differentiators. 

Sure, you can still write emails without the perfect pitch deck or even without a pitch deck at all. 

But everything falls into place when you have a strong narrative to guide the copy across your emails for your marketing and sales teams.

Your emails aren't a checkbox on your calendar.

They should feel like they are actually checking off your core ICP's "we need that" checkbox.

Here's a super tactical, strategic, and mind-blowing way to improve your B2B positioning and copywriting in 2026.

- Hire Ben Watkins
- Hire Ben Watkins
- Hire Ben Watkins

My hobbies for December. 

Also my hobbies from January through November.

Positioning is a lot like sports.

With any great team, you need an identity. And it doesn't matter how great you are at offense if your defense is horrible.

Because when you have great defense, it often leads to offensive opportunities.

B2B positioning is exactly the same way.

When you fix internal clarity, you fix how you express that message and identity across your industry.

They aren't stand-alone. They work with each other to build a unique and winning identity.

For example, category and differentiation lead what you say across your homepage, emails, and landing pages.

The value of what you offer plays into the messaging hierarchy and the strategic narrative you tell across messaging.

And building that strong POV is what gives you the firepower to deliver a clear sales story.

A lot of the mistakes across B2B startups are running an offense without a clear identity. Without a defense, when prospects ask questions about category or value differentiation.

When you build a great defense, building an offense is so much easier.

How are you dialing in your B2B emails?

Positioning gives you the roadmap. But there's always a challenge of getting that story onto your emails.

I created a mapping checklist for email. And it also involved asking the right questions:

- What copy formula aligns with the buyers' awareness?
- Where can I find the voice of the customer?
- Why won't prospects take action?
- How can I reframe stories to shift perspectives?
- What's the next "yes" I'm selling?
- What's generic that I can cut from the messaging?
- What's the cost of inaction?
- What's the enemy of my messaging?
- Is this message worth forwarding to someone I know?
- What would be the most highlighted sentence in this message?

These are questions I'm constantly asking as I write B2B emails (to bring that positioning to life).

Why is it so hard to show the value of your features?

Because we always stop at benefits (feels safer without getting overly promisy and maybe risky).

In B2B healthcare and life sciences, you need to continue to map it to a goal the customer is trying to achieve (h/t to April Dunford for this inspiration).

To get value clarity, you have to keep asking, "so what, so what, so what, so what" to drive home that specific question. 

But don't just arrive at a general vague business value that isn't attached to anyone or any scenario.

Your features to value mapping becomes more powerful when you can:

1. Attach it to a use case
2. Know the value clarity for who benefits the most
3. Know who loses the most with the consequences of not taking action

Getting more into the weeds with this stuff in the next few weeks.

There are too many positioning myths.

Part of it is because we want to believe we are the only unique healthcare startup doing amazing things.

Or maybe we think our features are super rad and clearly speak for themselves without any explanation.

The challenge is getting granular in four specific areas:

1. What's your market category
2. Who's your competition (including status quo)
3. Who's your best-fit customer (not just addressable market)
4. What's your value differentiation that matters to your best-fit buyers?

You don't solve this with a one-time exercise. 

You find this when everyone is aligned. You know what directions you can go in based on the problems you solve for your best-fit customers.

When you have direction, you know where (and who) you can help the most.

B2B healthcare positioning 101

Find out what makes your startup unique.

Then spend six to seven months getting approval to say it.

"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.

taplio

The Battle

Jess Cook

Benjamin Watkins

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The Battle

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Engagements

Likes

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