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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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/