Production

How Exit Five created B2B marketing's most beloved newsletter

By
Gareth Hancock
Published on
January 8, 2026
A well-crafted B2B newsletter can build real relationships and drive revenue. But most are generic, self-promotional round-ups of webinars and product releases that get ignored or filtered out of inboxes.
A well-crafted B2B newsletter can build real relationships and drive revenue. But most are generic, self-promotional round-ups of webinars and product releases that get ignored or filtered out of inboxes.

Exit Five is a rare exception that 40K+ B2B marketers are excited to read.

In this post, you’ll learn five core principles from Head of Content, Danielle Messler, that you can copy to make your own newsletter more successful.

1. Write for one reader at a time to build relationships

Write each issue as if you’re sending it to one person you know, not a buyer persona, to make your newsletter feel personal.

While most B2B newsletters act like link dumps, Danielle treats every Exit Five issue as a relationship-building channel.

“Today, I’m writing an email for Chelsea because I know she’ll care about this topic. Tomorrow, it’s Amruta, who just started a job where she’s managing an 80-person marketing org.”

That small shift changes the tone instantly.

Each email is focused on solving a real problem that others are looking to solve.

Danielle’s writing feels human and conversational because she’s willing to share her own challenges, successes, and failures:

Exit Five newsletter human-led content

Most B2B newsletters never go there, which makes Exit Five’s stand out.

They send two newsletters each week:

  • The Exit Five Weekly Newsletter (long-form strategic insights)
  • Marketing Snack (bite-size tactics)

Both appeal to different reading styles. However, they follow the same relationship-driven approach to drive organic growth.

Subscribers get double the value from a single newsletter, and Danielle gets richer data to keep improving content.

By comparing long-form and bite-sized version performance, she can see:

  • Themes that spark higher opens
  • Formats earning the most clicks
  • Where attention drops off

Those signals help Danielle fine-tune future issues, balance depth with speed, and prioritize the topics readers consistently crave.

2. Be transparent to drive trust and signups

Showing people what they’ll get from your newsletter before they subscribe removes skepticism and can increase sign-ups. 

Most B2B newsletters hide their content behind an opt-in form, which frustrates readers and makes them hesitant to opt in.

As Danielle explains:

“It’s a big ask. Our inboxes are packed with a lot of unwanted senders. To invite someone in, I think marketers have to prove why they deserve to get in the door.”

Exit Five overcomes skepticism by publishing previous issues on its newsletter landing page:

Framing the newsletter as a publication demonstrates what subscribers can expect.

It also makes it feel more thoughtfully produced with clear themes and consistent formatting, suggeting a higher editorial standard.

It also attracts the right audience: marketers who might later become community members.

This “try before you buy” approach:

  • Builds trust
  • Provides social proof
  • Reduces perceived risk

All without adding extra work for the team.

Transparency upfront helps turn more curious readers into subscribers.

3. Give readers a clear, actionable takeaway in every email

To increase engagement and loyalty, every issue should offer practical advice that readers can apply immediately.

Danielle’s rule is:

“Make sure there’s something in your newsletter readers can learn today. Something they can implement in some way.”

Sometimes, that’s a tactical hack. Others, a strategic framework or insight from industry research.

For example, Danielle breaks down Mutiny CEO Jaleh Rezaei’s growth strategy:

Exit Five newsletter growth strategy breakdown

Then, she explains exactly how readers can apply this strategy themselves:

Exit Five newsletter actionable next steps

To keep ideas fresh, Danielle turns to her audience and existing content to consistently deliver topics marketers care about.

Exit Five stays relevant and spots real pain points by:

  • Listening to community feedback
  • Monitoring trending conversations
  • Repurposing proven content from LinkedIn posts, podcasts, or other channels

Then, Danielle frames every newsletter angle with a new perspective and practical steps.

Founder Dave Gerhardt labels it Exit Five’s “content flywheel”:

A post becomes a newsletter, fueling feedback that feeds future content. This creates a self-sustaining cycle of actionable insights.

So, ditch the vague summaries.

Instead, focus your newsletter on usable insights.

“Avoid regurgitating information. Add narrative and a new angle. ‘Dave talked with this person, and here’s what they said about making sure your positioning is clear instead of broad, and here’s how to do it.’”

Instead of simply reposting content:

  • Extract the lesson from the original material
  • Add context that explains why it matters or how it fits into a bigger picture
  • Show readers how to apply it in their own work

That way, every email teaches something useful, keeps readers engaged, and gives them a reason to open the next issue.

4. Prioritize email replies to increase deliverability

Email responses are an opportunity to start two-way conversations with your subscribers and buyers. They also signal to email servers that recipients trust you with their inboxes.

While open and click-through rates matter, replies tell you who’s actually engaging while improving deliverability.

The simplest way to get replies is to ask for them.

Danielle includes value-led P.S. prompts to invite thoughts or reactions, which grabs the attention of readers who skim:

Exit Five often gets 30-40 replies per send. Almost unheard of in B2B.

Danielle has built this over time by replying to every message.

That personal touch builds trust and deepens relationships.

According to Dave Gerhardt:

“One other thing I love is Danielle's ‘PS’ tactic...super unscalable, right? She's going to email everyone the link to the article she mentioned? Yep. She will. And that's exactly why it works.”

Email automation is still crucial for B2B marketers. But it can’t replicate the human connection that spurs loyalty and advocacy.

5. Use curiosity-driven subject lines to increase opens

Exit Five’s most opened subject lines hint at relevant value within emails but withhold key details to boost open rates.

Zero Bounce research shows people are more interested in emails from work, friends, and family or brand discounts.

Relevance and subject lines are the top motivators for people opening brand emails:

Zero Bounce email marketing research

To improve open rates, Danielle creates a “curiosity gap” with her subject lines:

“The art of storytelling is withholding information, but you also want to give them just enough that they know it’s valuable.”

She pulls readers in by promising a payoff without giving it away:

  • “Here’s what to do when you’re not the subject matter expert”
  • “The mindset shift that helps marketing leaders move faster”

Honesty is the key to making these work. Your subject line must set a realistic expectation that’s fully delivered in your email.

Exit Five’s subject lines avoid clickbait. That consistency creates an expectation with readers that they can trust them to deliver value in future issues.

One way to write better subject lines is to study emails that you open.

Make observations in length, tonality, and psychological principles at play.

For example, you might open an email with the subject line: “The one shift that doubled our pipeline”.

Adapt this to your own emails.

For example, a product analytics brand might try: “The small shift that improves your onboarding flow”.

Track open rates over time to see which hooks resonate best with your audience.

Reward people’s curiosity with real value and watch engagement compound over time.

Start now instead of striving for perfection

Successful B2B newsletters show up consistently, write for humans, and share actionable insights.

You don’t need to nail the perfect format on day one. As Danielle says, you only figure out what works by getting reps in.

Start small, iterate fast, and improve with every issue.

Need help creating a newsletter people actually enjoy? Book a call today and let’s chat.

Share this post

Ready to scale your organic content?

Grizzle helps enterprise SaaS brands fuel their SEO engine with a proven content program.
Work and play—there’s no compromise
START A PILOT PROJECT

Get a proof-of-concept and scale your content engine

Here's what we'll cover in our 30-minute call:

  • Your content marketing and organic growth goals
  • Actionable advice based on real performance data
  • How we can get started with a "proof-of-concept" pilot project
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.