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Index/Sales/The Transaction
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Overcoming Your 'Go-To-Market Midlife Crisis' with Craig & Matt - Ep 57

The Transaction · 2025-06-12 · 55 min

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Topics in this episode

SaaSgo-to-marketFounderbusiness adviceC suite

Episode notes

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.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Guy Rubin - 2026 GTM BenchmarksCloud Radio · on SaaS95 / 100
  • April Dunford’s 1 Killer Question to Expose Weak AI Product Positioning [Repeat]LaunchPod · on SaaS94 / 100
  • Ep. 191 Andrew Lindsey, Chief Executive Officer at Flexnode | Data Center Go-to-Market PodcastData Center Go-to-Market Podcast · on go-to-market87 / 100
  • MicroConf Tactics: He Built Two Unicorns. Here’s The Only AI Startup He’d Build in 2026MicroConf On Air · on SaaS79 / 100
  • From ‘You’ll Never Make It’ to the C-Suite: Dr. DeRetta Rhodes, EVP & Chief People & Culture Officer, The Atlanta BravesExecutiveland · on C suite78 / 100
  • Reframing Marketing ROI to Return on Objectives with Karl Van den BerghThe B2B CMO Podcast with Jon Miller and Sydney Sloan · on SaaS75 / 100

More from The Transaction

All episodes →
  • How Founder POV Helps Sales Build Buyer Confidence with Jim Wilson, Partner at Costanoa Ventures - Ep 8485 / 100
  • Building Brand Momentum in Market with Carilu Dietrich & Maya Spivak - Live Session - Ep 8370 / 100
  • An Honest Reappraisal of Marketing Attribution with Dan Kimball, GTM Advisor - Ep 8276 / 100
  • Organizing Unforgettable Events for B2B with Jen Igartua, CEO of Go Nimbly - Ep 8176 / 100
  • The AEO Playbook: Own the AI Shortlist - Live with Sydney Sloan at GTM Tailwinds - Ep 8085 / 100
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