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/