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

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

Please join me in this celebration.

B2B Healthcare SaaS Positioning & Messaging | ☕️ Espresso connoisseur

"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

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.

Bienenstich or bee sting cake. 

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

No alternative text description for this image

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.

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.

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.

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

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.

"We're smarter, better, and faster."

B2B startups say this all the time.

But there's no clarity. Nobody knows what that means. But it sure does sound nice.

Omada Health is a great example of this (and how they avoided saying this).

They could have positioned themselves super broadly around chronic conditions, with multiple buyers, and lots of value props.

They could have said: "The digital health platform for chronic disease management and prevention."

And it would have been wonderfully generic and forgettable.

But that's not how they started in 2011. 

They picked a winnable, narrow edge:

"A CDC-recognized digital Diabetes Prevention Program that helps people with prediabetes lose weight and reduce their risk of Type 2 diabetes by 58% , delivered virtually with personal coaching, connected devices, and peer support."

They went narrow:

✅ One condition
✅ One clinical anchor
✅ One audience 

Only after proving that winnable narrow positioning wedge did they expand.

Now they have a million members across four chronic conditions. And they started with a sharp and narrow position.

Omada won by starting narrow, proving value, and earning the right to expand.

Good copywriting can't save bad positioning.

In a nutshell, your copy should never do these things:

❌ Written without clear positioning or a real offer 
❌ Built around lovely wordplay instead of customer language 
❌ Trying to band-aid weak differentiation instead of exposing and sharpening it 

It's like moonwalking without ever moving and mostly looking like a doofus. 

When you fix your positioning, it empowers your team with a story:

✅ The right buyers
✅The right category
✅ Why buyers should choose you

But then your emails and landing pages have actual power:

✅ Understand the Voice of Customer data
✅ Pull out the exact phrases buyers use for their pains and desired outcomes
✅ And assemble it into headlines, leads, and calls-to-action that actually get the right people to say “yes, yes yes!"

B2B healthcare and SaaS try to jump ahead with clever copywriting that sounds amazing

Instead, these startups should look at how to create foundational positioning:

- What's the market shift
- Why does this problem matter to your buyer
- What are the flawed framings and alternatives
- What category are you competing in
- What is your unique value in that category
- What's the proof that it works?
- What makes it different from competitors
- How does that become a roadmap for messaging?

This is how I help B2B startups build a positioning deck and then show what that looks like through a landing page or email with copywriting.

Get your positioning aligned and your copy will follow.

Problems. Desires. Outcomes. Alternatives. Market.

Reddit is a goldmine for this.

You find phrases from your customers on how they think of the market, a failed solution, or a failed competitor. They tell you unfiltered thoughts.

On the positioning side, you can find patterns of where past early stage startups went wrong. 

You can feel the honesty. The emotion. The messiness.

And it's super helpful if you're trying to find what your buyers think of a certain problem in a certain context.

Perplexity Labs is amazing at finding this.

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.

Positioning comes before emails and landing pages.

Startups often work backwards because they want to get as much out there without having a real direction.

But positioning is essentially your map. Positioning sets the context, the problem, and the frame, and is how you position your emails and landing pages. 

You know where you're going because of where you came from.

When I help B2B healthcare startups with positioning, I'm giving them a direction so they know what story to tell. 

And that story is expressed across emails and landing pages through outbound, nurture, and paid landing pages.

You want to avoid working backwards:

1. Send emails hoping something lands
2. Whichever gets the highest click determines positioning
3. Make that winning email your positioning story

Vs.

1.  Identify competitive alternatives, unique capabilities, and best-fit customers
2. Turn that into a product story 
3. Write conversion copy that sharpens that story

The latter requires way more work and actually mapping out a process. And it almost  always takes months to validate. 

But it's worth it because it gives your team a roadmap.

Three of the most common mistakes I saw from B2B healthcare companies in 2025:

1) Not hiring Ben Watkins
2) Not hiring Ben Watkins
3) Not hiring Ben Watkins

Please avoid this mistake at all costs in 2026.

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

Jessica Walrack

Jessica Walrack Copy and Content

I am a professional freelance finance writer and journalist with 11+ years of experience writing and have a background in retail and B2B sales. I specialize in SEO-optimized personal finance articles and write for some of the leading media sites in the U.S. including CNN Underscored, U.S. News and World, Fox Money, and CBS News Moneywatch. 

I am very experienced with all parts of the content development process from SEO research to publishing. I love jumping onto teams and working with editors to create awesome content that drives results.

I am currently only providing freelance writing services for blogs and articles in the finance niche.

Check out my work and the results I drive on my website: https://jessicawalrack.com/

Want to chat about an upcoming project? Send me a DM!

Freelance Finance Writer and Journalist

CBS MoneyWatch

CBS MoneyWatch, a division of CBS News and a property of Paramount Global, is a personal finance website that provides advice on retirement, investing, money, work, and real estate. I provide them with blogs on various personal finance topics.

Freelance Personal Finance Writer

U.S. News & World Report

I’ll be contributing stories on a freelance basis to the money column.

Freelance Contributor

USA TODAY

I review personal finance articles and add insights to them.

Advisory Board Member

Investopedia

Investopedia has been helping readers through its financial news; original studies, research, data analysis; and best-in-class educational content for 21 years. I'm happy to be one of 840 contributors helping more than 44 million monthly readers find answers to empower them to take control and improve their financial lives.

Contributing Personal Finance Writer

All Things Freelance Writing

We are on a mission to create a lively, fun, and empowering freelance writing community that helps solopreneurs build thriving writing businesses they truly enjoy.

We envision a future community of millions of freelance writers helping one another run successful businesses they enjoy that also set them free to achieve other ambitions in life.

Find us on LinkedIn, Instagram, our Blog, our Shop, our FB group, and our podcast!

Performex Media Inc.

Performex Media is a creative content marketing agency that provides stunning media and engaging written content to drive results for our clients. I run all aspects of the written content side of the agency.

Co-Founder and COO

Forbes

Freelance Writer

Money

I write SEO-optimized personal finance content for the company which are published in newspapers across the U.S.

Personal finance freelance writer

The Balance

The Balance is among the top-10 largest finance properties as measured by comScore, a leading Internet measurement company, and helps over 100 million readers each year. We share in our mission to make personal finance easy to understand so it was a perfect place for me to jump on board and regularly contribute high-quality, search-optimized articles.

Personal Finance Writer

Freelance Finance Writer and Journalist 👩🏻‍💻🧲 | Business and Personal Finance Blogs | On-page SEO is my second language | U.S. News and World, Investopedia, & More | Founder of All Things Freelance Writing

Hi! I’m Jessica, a full-time freelance finance writer and marketing strategist with 10+ years of experience.

If you're looking for blogs, stories, or long-form content on finance-related topics, let's chat!

I cover mortgages, loans, credit cards, investment accounts, insurance, budgeting, and more.

My promise? Great content, no headaches!

You can find my work featured on many authority sites including CBS News MoneyWatch, US News, NewsWeek, USA Today, MSN Money, The Balance, Biz2Credit, The Simple Dollar, Interest, Investopedia, Commonbond, Supermoney, Bankrate, NextAdvisor, Guardian, Personalloans, as well as on hundreds of business websites.

I’ve helped my clients to rank at the top of the SERPs while engaging their human audience to drive specific results.

You can hire me to:

1️⃣ Write content and copy. ✍️

2️⃣ Edit/revamp existing content. ✅

I often work remotely with Founders, CEOs, Agency Owners, and Creative Directors. I love partnering with tight-knit teams!

What my clients are saying...

"Jessica is one of the best writers that we have ever worked with - she is very organized, structured and has great attention to detail. I've been in finance for over two decades and am super particular about what I'm looking for in our articles and writers - she is one of the very few that I've ever worked with where NO rewrites or edits were needed. We highly recommend Jessica!" -Jennifer Lammer, CEO, Founder & Chief Chef @ Diamond NestEgg

“I worked as Jessica's editor on a number of projects at ClearVoice. She is an amazing writer! She has incredible attention to detail, especially with complex subject manner and intricate style guides/briefs. Her copy is easy-to-read, error-free, engaging, and always nails the client's intended tone. She really excelled in the personal finance niche and was always one of my go-to writers for new assignments. I am always happy to send work her way because she makes my job so easy. I hope to keep collaborating in the future!” -Kristy Snyder, Editor at Clearvoice

Want to work together? DM me to see if we're a good fit!

I’m also the founder of All Things Freelance Writing. A community that helps freelance writers build profitable businesses they enjoy. Join 6.7K+ freelance writers who get our free jobs email every Friday!
https://allthingsfreelancewriting.beehiiv.com/

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The Battle

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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);}Benjamin Watkins's LinkedIn Performance

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