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

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The Transaction

Craig Rosenberg & Matt Amundson | B2B Sales & Marketing Experts - Hosts of The Transaction

72 episodes

1 day ago

Welcome to The Transaction. The #1 Go-To-Market podcast on the planet. Hosts Craig Rosenberg and Matt Amundson, two legendary go-to-market leaders in their own right, talk weekly with the best sales, marketing, operations, and product leaders in the B2B SaaS world to understand what's working in the new playbook of the post-ZIRP market. But Craig, Matt, and their guests don't just talk theoretically, they share the stories and actionable tips, tactics, and strategies behind what's driving revenue growth that you can take and implement in your own go-to-market roles. Whether you're a Chief Revenue Officer leading a B2B SaaS sales and marketing organization, a marketing leader trying to drive bigger outcomes with your demand gen team, or a new sales rep, you'll learn and laugh every episode. From ABM to PLG, from MEDDIC to MEDDPICC, the world of business is constantly evolving. We’ll cover the who, what, where, when, why and most importantly how you get… The Transaction. About Your Hosts Craig Rosenberg is the Chief Platform Officer at Scale Venture Partners. He is a seasoned expert in B2B revenue growth, helping SaaS companies transition from founder-led growth to becoming high-growth Go-To-Market machines. Previously, Craig was a Distinguished VP Analyst at Gartner and co-founder of TOPO Inc., a research and advisory firm acquired by Gartner in 2020. Craig thinks Die Hard is a Christmas movie. Matt Amundson is the Chief Marketing Officer of DuploCloud. He is also an advisor for companies such as Sendoso and Salesloft. Prior to DuploCloud, Matt spent time as an Executive In Residence with Scale Venture Partners and led marketing departments at Census, Very Good Security, and Everstring, to name a few. Matt thinks Die Hard 2 is better than Die Hard. The Transaction is produced by Sam Guertin.

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

The Transaction

55 minutes

5 months ago

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

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

Maria Pergolino: https://www.linkedin.com/in/mariapergolino/
Kristina McMillan: https://www.linkedin.com/in/kristinamcmillan/
David Boskovic: https://www.linkedin.com/in/dboskovic/
Jill Rowley: https://www.linkedin.com/in/jillrowley/
Jill Rowley’s tweet calling Craig’s Blackberry in 2012: https://x.com/jill_rowley/status/187231284970536960
SaaStr
Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/
Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/
Copy.ai
Klarity: https://www.klarity.ai/
Sydney Sloan: https://www.linkedin.com/in/sydsloan/
Mandy Dhaliwal: https://www.linkedin.com/in/1mandydhaliwal/
Jake Dunlap: https://www.linkedin.com/in/jakedunlap/
James Kaikis: https://www.linkedin.com/in/jameskaikis/
Jordan Crawford: https://www.linkedin.com/in/jordancrawford/
Jordan’s Episode: https://open.substack.com/pub/thetransaction/p/inverting-your-go-to-market-strategy?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false

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