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On the show today, I have Collin Mayjack, Principle Product Marketing Manager at GoFundMe.
Before joining GoFundMe, Collin worked in product marketing at Oncue and Dataro and is the creator of Holy Shift.
What you’ll learn from Collin in this episode:
Why Collin believes clarity always beats cleverness in B2B messaging—and how to avoid “junk food” copywriting
The seven messaging principles Collin uses to drive alignment across product, marketing, and sales
How to translate complex products into human-first stories that resonate with buyers (and actually get repeated by sales)
The secret to testing messaging without fancy tools—including Collin’s scrappy process using real customer calls
How to navigate internal messaging politics—balancing SEO, brand voice, and product truths without losing the message
A framework for driving influence across teams—even when you don’t own the pen or the process
How to write messaging that sticks: Collin’s 20-second talk track technique that sales teams love
Why side projects are the ultimate messaging gym—and how they make you a stronger communicator at work
A fresh take on feature vs. benefit messaging (hint: your buyers are smarter than you think)
How Collin builds buy-in by leading with positioning before assets—and how you can do the same
And so much more.
Collin’s 7 Messaging Principles
Clear is better than clever
Lesson: Clarity should always win.
Clever copy might feel fun to write, but if your buyer doesn’t immediately understand what you do, you lose.
“I know you want to write this clever tagline, but if people don’t know what it means, it just doesn’t matter.”
Best case: clear and clever.
Worst case: unclear and confusing.
Differentiate or die
Lesson: Your homepage shouldn’t hide your advantage.
If your differentiators don’t show up until the demo, you're too late. Position what makes you unique early and often.
“Buyers weren’t finding out what really made us different until they got into a sales pitch. It’s a little too late.”
Jargon is the enemy
Lesson: Speak like a human.
Internal buzzwords and vague phrasing sound smart, but confuse people. Say it like you would at a BBQ.
“Create memorable donation experiences” means nothing. Say: “Build a beautiful campaign page.”
You can’t say it all, focus
Lesson: Trying to cover everything means you say nothing.
Especially with platform products, resist the urge to list every feature. Lead with what your buyers love and what you’re best at.
“They love our donation pages—let’s lead with that. Don’t water it down to check every box.”
Customers do care about features
Lesson: Features are how benefits become believable.
We’ve overcorrected from “features don’t matter.” They do. Especially when they help buyers trust that the benefits are real.
“Every B2B tool says it saves time or money. What matters is how—and that’s the feature.”
Talk to your champion like a human
Lesson: Message to the internal advocate—no one else.
Your champion is the person selling your product internally. Don’t water the message down to please the C-suite.
“You can make a landing page for execs. But your main product website? That’s for the champion.”
Good messaging flows from good positioning
Lesson: If your messaging doesn’t reflect your strategic edge, it’s disconnected.
There should be a clear line from your market position → to your key value prop → to your message.
“If our corner is flexibility, and our messaging doesn’t scream flexibility, we’ve missed the mark.”
Here’s what’s covered in our conversation:
01:33 – From pastor to product marketer: Translating complexity into clarity
03:53 – Why side projects make you a better writer and messenger
06:17 – The origin of Collin’s 7 messaging principles
08:32 – #1: Clear is better than clever (and why most messaging fails here)
09:57 – #2: Differentiate or die—how to bring product strengths to the surface
10:55 – #3: Jargon is the enemy—cut through corporate fluff
11:25 – #4: You can’t say it all—focus on what matters most
12:24 – #5: Customers do care about features (with a twist)
14:21 – #6: Talk to your champion like a human
15:50 – #7: Good messaging flows from good positioning
18:22 – Bonus: The best messaging is clear and clever—but clarity wins
19:17 – How Collin tests messaging without fancy tools (and why he goes rogue)
20:44 – Partnering with PMs to pitch new features to real customers
21:43 – Using customer reactions to validate and refine messaging
22:37 – Real-world naming feedback: letting customers vote live
23:31 – Testing messaging in startups vs. larger companies
24:49 – Scrappy tactics: using social, email, and founders to test ideas
26:00 – How to choose the right customers for feedback
26:58 – The politics of advisory boards and enterprise obsession
28:11 – The PMM cheat code: bring the story, get invited to the table
29:04 – Balancing product messaging with SEO and brand voice
30:33 – Winning influence by starting with positioning, not copy
31:31 – Using Emma Stratton’s VBF framework to earn trust and traction
33:01 – The “mild sauce” effect: how messaging evolves through compromise
33:59 – The power of pen-to-paper: why the strategist shapes the outcome
35:45 – Influence, humility, and the politics of feedback
36:43 – Why being likable matters more than being right
38:10 – How Collin enables the sales team with clear, human messaging
39:21 – “Tuesdays with Enablement”: internal sessions that drive adoption
40:14 – How Collin builds 30-second sales stories that actually stick
41:43 – The James story: an example of sales messaging that works
43:07 – Talk tracks over taglines: why real talk wins
43:49 – Being active in Slack and jumping on sales calls to support deals
44:55 – Lightning round: One messaging tip you can implement tomorrow
46:21 – What is living all about? Collin’s personal reflection
47:00 – Where to find Collin and lift him up
👉 Where to find Collin
LinkedIn: https://www.linkedin.com/in/collinmayjack/
Holy Shift Podcast: https://www.linkedin.com/company/holy-shift-pod/
👉 Where to find Josh
LinkedIn: https://www.linkedin.com/in/joshua-chronister/
YouTube: https://www.youtube.com/channel/UCUdKBktrLJWzNMDS45fh_Bg
🎙️Referenced
Alex Eaton: https://www.linkedin.com/in/alexeaton1/
Mark Huber: https://www.linkedin.com/in/markehuber/
Gab Bujold: https://www.linkedin.com/in/gabriel-bujold/
Zach Messler: https://www.linkedin.com/in/zachmessler/
Anthony Pierri: https://www.linkedin.com/in/anthonypierri/
Emma Stratton: https://www.linkedin.com/in/emma-stratton-punchy/
Created by Josh Chronister
I interview the best product marketers and tech companies who create messaging that resonates with their buyers. Come learn from them, so you can hit ‘Publish’ with confidence.
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