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.
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What you’ll learn:
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.
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In our conversation, we cover:
00:00 – Intro: Welcome Collin Mayjack to the show
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
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👉 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/
Substack: https://onmessaging.substack.com/
YouTube: https://www.youtube.com/channel/UCUdKBktrLJWzNMDS45fh_Bg
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🎙️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/
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit onmessaging.substack.com
