The Transaction | Overcoming Your 'Go-To-Market Midlife Crisis' with Craig & Matt

Overcoming Your 'Go-To-Market Midlife Crisis' with Craig & Matt - Ep 57

June 12, 2025 / 55:11/S2:E57

That’s right, no guest on this one, but not to worry, it’s just as insight-filled, yet off the rails, as all of our other episodes that you’ve come to know and love. Co-Hosts Matt Amundson and Craig Rosenberg discuss coming to terms with their go-to-market mid-life crises and how they have gotten up to speed on the latest AI advancements to help them get back in the game. Craig and Matt dig into how they’re using AI tools to create things like AI buyer personas, the impact B2B events are having, and what the new go to market playbook is beginning to look like.

Also, Matt reveals his devious guilty pleasure and Craig shares how he lost his children in the desert.

Critical Takeaways

Instead of prompting AI like a search engine, leaders should teach their teams to treat it like a colleague. Matt’s breakthrough came when he asked ChatGPT how to build personas and what information it needed to do so. By asking “how do I build X?” instead of “give me X,” teams unlock faster, higher-quality outcomes.
Adopt a “Shock & Awe” mindset to break through. The market is saturated and fatigued—practical content alone isn’t enough. As Craig put it, GTM teams need to pair insight with surprise to break buyers’ patterns. Leaders should push teams to experiment with bolder formats, storytelling, or AI-powered personalization that “breaks the frame.”
Account Research with AI is now table stakes for sales and marketing teams. Using AI for account research (before, during, and after sales calls) is no longer optional. Craig emphasized this is the new baseline expectation. If your team isn’t using tools like ChatGPT or Perplexity to prep on accounts and individuals before outreach, you’re behind.
Before adopting any AI vendor solution, ask: “Can my team do this directly in ChatGPT or another general model?” As Craig noted, many startups at SaaStr were pitching account prep workflows that anyone can already do with a simple prompt.

Chapters

00:00 Episode Preview

03:30 The GTM Midlife Crisis Hits – Why the old playbooks stopped working

06:15 Building a New Playbook with AI in the Go-To-Market Hacker era

08:45 Matt’s AI Buyer Persona Workflow – How to build and deploy AI agents for feedback

13:15 Talk to Your AI Tools Like People

17:00 999/1000 Accuracy Rate – Why AI is now a mission-critical content editor

25:30 Account Research is the New Minimum – How GTM teams are winning with better prep

30:00 Matt & Craig just Want to Watch the World Burn

37:00 Events Are Back, Baby – People crave new insights and in-person energy

40:00 LinkedIn has changed, but it is still the social platform of choice for B2B brands

45:00 Video Content: Raw vs. Polished – When it’s time to scale production (and when DIY still wins)

50:00 Lost in the Desert: A GTM Parable – Craig’s real-life ATV crisis ends with a 10-year-old roasting him

Epic Quotes

“ It's the age of the Go-To-Market hacker.” - Craig Rosenberg
“ Everybody needs to create a custom GPT. And if you want to know how to do it, just ask it. How do I create a custom GPT here?” - Matt Amundson

Shoutouts