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Hello and welcome to the Exit Five Weekly Newsletter — read by 42,000 B2B marketing professionals around the world. Exit Five is a membership site designed to help you build a successful career in B2B marketing. Join 5,700 other members at exitfive.com.
By the way — this email was designed in Knak, which helps you create email and landing pages in minutes without having to write code. Learn more about Knak here.
TOGETHER WITH CUSTOMER.IO
🧪 10 Growth Marketing Experiments Worth Stealing
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Want to skip the trial-and-error and get right to what works?
The team at Customer.io just dropped a new playbook that documents 10 growth marketing experiments they’ve run across the full customer lifecycle, from acquisition to churn and win-back.
What’s inside isn’t fluffy “tips.” These are real experiments with clear hypotheses, tested methodologies, and results.
You’ll learn:
- How one change to a trial expiration email increased checkout rates by 46%
- Why a plain-text welcome email outperformed its prettier HTML version in long-term revenue
- The small tweak that boosted activation rates by 417% (yes, you read that right)
- And how a multi-stage churn campaign uncovered the hidden metric that best predicts churn
It’s the kind of resource that sharpens your thinking, and gives you the ammo you need to run smarter experiments yourself.
Grab the playbook here and bring a few of these ideas into your next growth meeting.
💻 How HubSpot's AI Marketing Leader Actually Uses ChatGPT

By 2027, Gartner predicts 95% of the B2B buyer journey will start in an LLM (vs 80% on Google today).
So instead of searching "how to create Facebook ads that convert," buyers will just say "give me Facebook ads that convert."
What this means: Informational content is worthless. You need to win at awareness and post-click experience.
Kieran Flanagan leads 300+ marketers at HubSpot and lives in ChatGPT. Here's what he's learned about AI for B2B marketers.
How Kieran Actually Trains ChatGPT
Most marketers suck at prompting because they wing it. Kieran's different.
He has 12 custom GPTs trained on different prompt frameworks. When he finds something that works, he creates a custom GPT to turn conversations into prompts.
His process:
- Find winning frameworks (like when Cursor's system prompt leaked)
- Extract core learnings with O3
- Train a custom GPT on those learnings
- Let the GPT craft prompts for specific outcomes
Example: "I want a campaign that's quirky, runs 30 days, and generates 100 customers" → The trained GPT creates the full prompt.
Tool Stack That Actually Works
- ChatGPT: For everything. Memory = lock-in. "ChatGPT is literally my friend."
- Claude: Better for team projects and business integrations. Access to 8,000+ tools through Zapier's MCP.
- GenSpark: For presentations. All of Kieran's best decks come from here.
Pro tip: Don't prompt tools directly. Have O3 read the tool's documentation and craft the prompt for you.
The Creative Partner Problem
"AI is not a great creative partner" = You can't prompt.
Most marketers create average content at scale. But if you're skilled at both copy AND prompting, AI becomes incredible.
The swipe file approach: Train AI on what's good. Show examples. Be specific about outcomes.
The New Marketing Divide
You need to pick a lane:
- Technical: Think like an engineer. See everything as a workflow. Figure out where AI fits to 10x human output.
- Creative: Be at the outer edges. Ideation, storytelling, copy that can't be replicated.
The dangerous middle ground? "Good enough" work that AI already does better.
The Bottom Line
AI fatigue is real (Kieran was prototyping software, optimizing investments, and solving legal problems at 11:30 PM recently).
But for marketers who love the craft? We’re in the golden age.
The admin overhead is gone. The creative possibilities are endless.
Time to pick your lane.
P.S. One overrated AI use case Kieran could do without? LinkedIn comments. Just stop.
📺 UPCOMING EVENTS
💪 [July 23rd] The Exit Five AI Throw-Down: A Live Battle of the Best AI-Driven Content Workflows in B2B Marketing

B2B marketers everywhere are experimenting with AI to scale content, but who’s actually getting results?
We’re bringing those marketers front and center to show you how it’s done.
This live session will feature five finalists who submitted how they’re using AI to power their content engine. Each one will take the (virtual) stage to demo their process, show results, and answer questions from our expert panel:
- Benny Bridger (Head of Marketing, Walnut)
- Jess Cook (Head of Marketing, Vector)
- Dave Gerhardt (Founder, Exit Five)
It’s part workshop, part competition, with bragging rights and a pair of Meta Ray-Bans on the line for the top use case.
Expect behind-the-scenes workflows, creative tools in action, and lessons you can take back to your own team.
Think you’ve got the most creative AI workflow?
Submit your use case by July 15th for a chance to be one of the five featured marketers. All you need is:
- A quick write-up
- A 2-minute Loom demo
- Any results or metrics you can share
🏢 Open Roles
Who's hiring right now?
🔥 HOT JOBS OF THE WEEK:
NewtonX is hiring a Strategic Marketing Advisor to share expert insights through surveys and consults that shape B2B decisions. The ideal candidate is a seasoned marketer who wants to get paid for sharing smart takes, on their schedule, no strings attached.
Other open roles on the Exit Five job board this week:
- Directive is hiring a Demand Generation Manager
- Tiugo Technologies is hiring a Senior Web & Brand Designer
- RightRev is hiring a Marketing Manger
- Paramark is hiring a Marketing Manager
- Paramark is hiring a GTM Enginne
- Ankored is hiring a VP of Marketing
- Science Interactive is hiring a Producat Marketing Mangager
- Animalz is hiring a Senior Content Marketer
- Ceipal is hiring a Director of Content
- New North is hiring a Growth Marketing Strategist
- Quarterzip is hiring a Senior Growth Marketing Manager
- The Virtual Hub is hiring a Head of Growth Marketing
Have an open role and want to make sure the best B2B marketing talent sees it? Just reply to this email and we'll send over more info on how you can post it on our job board + get it in front of 42k+ marketers.
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