Imagine you created a sales process so amazing that it was the only one customers actually enjoyed. Impossible? Today’s guest says no.

Returning once again to grace this humble GTM-focused podcast with his immense intellect and immaculate presence is Brent Adamson, the co-author of The Challenger Sale and the upcoming new release, The Frame-Making Sale. Brent is back alongside Co-Hosts Matt Amundson and Craig Rosenberg to share how sellers can help B2B buyers become more confident in their own buying decisions, why “frame making” needs to be part of every seller's mindset, and how to tell powerful, emotionally engaging stories.

Also, Craig confronts his own fleeting mortality, Matt says he likes “the big pullout”, and Sam the Producer contributes by swearing.

Critical Takeaways

• Modern B2B buyers are overwhelmed and uncertain. Top-performing reps succeed by helping buyers build self-confidence in their decisions, not by pitching harder or throwing more whitepapers at them.
• The biggest predictor of successful SaaS deals isn’t objection handling, it’s whether the buyer believes they’re making a good decision. Sales teams should focus on guiding internal alignment and validating the decision process.
• Stop selling like you’re the expert and start selling like a guide. SaaS buyers want to see and hear what similar companies are doing when in their position. Social proof beats thought leadership when it comes to moving deals forward.
• Customer indecision is the real killer of your pipeline. B2B Buyers who feel overwhelmed delay action, your job is to make progress feel easy and safe.
• GTM leaders should train reps to speak with emotional clarity, using language that reflects how buyers feel, not just what they need to know.
• AI can’t replace human trust in B2B sales. Even as automation takes over task work, the real differentiator in SaaS GTM will be emotional connection and the ability to de-risk complex decisions.
• Vulnerability builds trust. Whether it’s storytelling, deal coaching, or just acknowledging awkward moments, honesty closes more than clever pitches.

Sponsored Segment

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 - Episode Preview

02:05 - Introducing Brent Adamson & Reliving the Maggots on a Plane Story

06:40 - Brent Recounts a Near-Death Experience, Courtesy of United Airlines

12:26 - The Origins of Brent’s Latest B2B Sales Research

16:15 - Why B2B Buyers Want a Rep-Free Buying Process & The Importance of Human Connection in Selling

19:35 - Customer Decision Confidence is the Biggest Factor in Driving High-Quality, Low Regret Deals

26:50 - B2B Sellers Need to Help SaaS Buyers Learn How to Buy Solutions Intelligently

31:26 - Sales Psychology will Play an Even Larger Role in B2B Moving Forward

37:49 - SaaS Sales Reps Need to Become Buying Coaches for their Prospects

41:18 - How to Increase Customers’ Confidence in Their Own Buying Decisions

48:32 - The Key to Telling Compelling, Emotionally Engaging Stories

53:25 - How Addressing the Elephant in the Room, like Bloody Eyeballs, can Create Better Human Connections  

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ When things like that make you nervous, uncomfortable, you don't run away from them you have to run right at 'em.” - Brent Adamson

Connect with Brent Adamson

• LinkedIn: https://www.linkedin.com/in/brentadamson 
• The Framemaking Sale: https://a.co/d/iQhqSzq 
• Website: https://www.brentadamson.net/ 
• A to B Insights Website: https://atobinsight.com/ 

Shoutouts

• Brent’s Last Episode: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyer
• Coffee with Brent Adamson & Matt Heinz: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ 

What if cold calling isn’t dead—but everything we know about it is?

From dissecting permission-based openers to dunking on dated tactics, sales experts Justin Michael and Charles Needham make a bold case for why the phone isn’t dead as a sales channel—it’s just misused. 

Justin Michael, aka the John Wick of executive coaching, is a longtime B2B seller and sales trainer, as well as the Founder of the Justin Michael Method and co-author of The Cold Call Algo. Along with being Justin’s Co-Author on Cold Call Algo, Charles Needham is a bona fide B2B Sales Badass in his own right, being the Founding Account Executive at TitanX and the Founder of Needham Advisory Group. Joining co-host Matt Amundson for this episode, Charles and Justin dig into the unique benefits of cold calling, the evolving role of Sales Development Reps, and where sales orgs should be trying to implement AI sales tools.

Critical Takeaways

• Encouraging SDRs to see cold calling as a means for intelligence gathering rather than merely scheduling meetings can lead to better insights and long-term relationships.
• The traditional methods of cold calling, like repetitive sales scripts, are losing effectiveness. Incorporate permission-based openers and insightful questions early in the call to create curiosity and engagement.
•  Leveraging AI to clean and target data can dramatically increase the effectiveness of your outreach strategy. By focusing only on prospects who are likely to answer, teams can improve their connect rates and overall outcomes.
• Train teams to focus on tonality and pacing during calls. Using neutral, calm tones, can help in calming down the prospect's initial resistance and opening up a more natural conversation.

Chapters

00:00 Intro

01:09 Introducing Justin Michael and Charles Needham

02:55 Discussing B2B Sales Strategies and Cold Calling as an effective sales channel

03:37 Justin's B2B Sales Stories and Experiences

08:07 Charles on Modern Sales Challenges for SaaS Startups

13:22 The Emerging Role of AI in B2B Sales Today

17:10 Cold Calling Sales Techniques and Best Practices

30:29 Debating Cold Call Openers

32:53 Unified Theory of Cold Calling for B2B sales

39:03 Mastering Tonality and Rhythm during B2B Sales Calls

56:26 The Future of Cold Calling

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “Cold calling is a mechanism to survey the market and have conversations, rather than going in there like 8 Mile Eminem style—one shot, one opportunity to book a meeting.” - Charles Needham
• “Problems are isolating by nature. So if you can show someone that it’s common, they’ll open up more.” - Charles Needham
• “ People buy emotionally, they justify with logic.” - Justin Michael

Connect with Justin Michael

• LinkedIn: https://www.linkedin.com/in/michaeljustin/ 
• Website: https://www.salesborgs.ai/ 
• Get the Book: https://coldcallalgo.com/ 

Connect with Charles Needham

• LinkedIn: https://www.linkedin.com/in/charles-needham/ 
• TitanX Website: https://www.titanx.io/ 

Shoutouts

• Kai-Fu Lee: https://www.linkedin.com/in/kaifulee/ 
• AI Superpowers: China, Silicon Valley, and the New World Order by Kai-Fu Lee: https://a.co/d/ex6F2Yz 
• David Dulany: https://www.linkedin.com/in/davidkdulany/ 
• Wyzer.ai
• Mike Bosworth: https://www.linkedin.com/in/mikebosworth/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

In the second episode of 'The Direct Deposit,' Matt Amundson and Craig Rosenberg dive into the astonishing growth of Cursor, a startup providing an AI code editor for software developers, that has secured three funding rounds and achieved $500 million ARR in less than a year—all without a traditional marketing strategy. Matt & Craig explore how Cursor's product-led growth go-to-market model and simple SaaS pricing tiers contribute to their success in both raising new funding rounds and recurring revenue. Plus, there's a debate over the relevance of a traditional Go-To-Market team for such early-stage startups creating AI products. We also briefly touch upon Matt's favorite movie, John Carpenter's 'Big Trouble in Little China.'

Join the newsletter to get new episodes straight to your inbox! Join here: https://thetransaction.substack.com/

Enjoy this episode? Share it with a friend!
Believe it or not, even in the tech-fueled world we live in, the number one way podcasts grow is word of mouth. So, if you learned something, lost your cool at something, or laughed at something from the show, give us a hand by sharing this with someone else who will get that same value from the show, regardless if it's education, entertainment, or outrage-inducing.

Everyone's talking about how amazing AI can be, but there’s a real dearth of actionable advice on how to actually put generative AI to work for your sales, marketing, customer service, or other go-to-market team. Well, that was until we talked to this week’s incredible guest…

Jake Dunlap is truly a thought leader on using AI in B2B go-to-market strategies and is the CEO of Skaled Consulting, a revenue performance agency dedicated to helping B2B companies scale smarter. Jake joins Matt Amundson and Craig Rosenberg to delve into the tactical and practical ways he is implementing AI tools into go-to-market motions and how you can get the benefits of new AI technology. Jake and Matt have both been building some interesting agents and custom GPTs, and they get into how they set them up and how they are using them. Jake discusses why B2B sales leaders need to stop managing by measuring sales rep activity, how to avoid major pitfalls when implementing generative AI tools in your organization, and how to build an efficient and effective outbound strategy today. 

Also, Craig shares that both of his cars were stolen straight out of his driveway, Matt remembers the name of a consumer product, and Producer Sam interrupts to ask a question about podcasts.

Critical Takeaways

• Train your sellers to think critically. Don't just provide templates. Teach your sales team how to analyze trends, customize outreach, and add value based on their understanding of the buyer's industry and challenges. Encourage creativity and problem-solving skills.
• Measure outcomes, not just the activities of your sellers. Shift your focus from tracking the sheer volume of sales activities to measuring meaningful conversations and outcomes. The quality of interactions should take precedence over the quantity.
• Start using AI to improve bottlenecks that you or your team are facing. While there are myriad amazing things you could do with AI, by focusing on the boring, unsexy things that constrain your revenue team, you’ll actually drive greater outcomes for your team.
• Sellers, try doing the type of outreach that isn’t massively scalable, but that provides immense value and really sticks out. This is likely going to yield better results than hitting ‘send all’ again. For example, you could use new AI tools like Deep Research and NotebookLM to create customized podcasts and white papers tailored to the specific role and industry needs of a contact at a target account.
• AI is not a go-to-market strategy in and of itself, nor is it something that can be applied in a blanket fashion across every role or function. 
• Let sellers play to their strengths. For example, some reps are great on video, while others excel on the phone. Don’t force every sales rep into the same volume-driven mold. Focus on outcomes, not activities.
• Don’t wait for Enablement to hold your hand and train you on using AI. As Jake said, “ sales leaders, executives, listen to me. You have to learn this yourself. You cannot outsource this through rev ops.” Why is that? Because AI is more than just another tech tool, it’s a fundamental shift in problem-solving. Don’t sit around waiting for a playbook—experiment, build, and iterate. Training wheels are for losers… and small children.

Chapters

00:00 - Episode Preview

00:36 - The Fast & The Furious: Silicon Valley Drift

07:39 - Two Insightful Examples of How B2B Companies are Using & Operationalizing Gen AI

11:41 - Why B2B Sales Reps Need to Start Using AI for Account Research & How to Get Started with New AI Tools 

13:36 - How to Build AI Agents for Each Buyer Persona & How Matt is Using AI as a Chief Marketing Officer

16:08 - The Power of Building Custom AI Agents for Revenue Growth

22:22 - B2B Sales Leaders are Still Getting Stuck on Activity Metrics, When They Should Measure Impact

30:04 - How to Construct a Successful B2B Outbound Strategy in the Current Market

37:01 - How Will Anthropic and OpenAI’s Custom GPTs Integrate with Existing SaaS Tools & Will Gen AI Tools Replace the Go-To-Market Function as We Know It?

42:01 - What Hurdles to Avoid When Implementing AI Tools in Your Company & Why Leaders Need to Stay on Top of AI Advancements

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “Stop asking the question, ‘What’s our AI go-to-market strategy?’ It’s not the right question.” - Jake Dunlap
• “The goal are the outcomes, not the activities.” - Jake Dunlap
• “Outbound never ends. You cannot take a project-based mindset to outbound.”  - Jake Dunlap

Connect with Jake Dunlap

• LinkedIn: https://www.linkedin.com/in/jakedunlap/ 
• Website: https://skaled.com/ 
• The Innovative Seller (Jake’s Book): https://www.jakedunlap.com/the-innovative-seller 

Shoutouts

• Dirty Mike and The Boys: https://youtu.be/1FkK8ZFE7Y0?si=WpJ9miacA2CdLq0u 
• NotebookLM: https://notebooklm.google/ 
• The Goal: A Process of Ongoing Improvement by Eliyahu M. Goldratt & Jeff Cox: https://a.co/d/03F3RE2 
• Matt Heinz: https://www.linkedin.com/in/mattheinz/ 
• Matt’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/how-to-implement-ai-in-your-go-to?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• Sydney Sloan: https://www.linkedin.com/in/sydsloan/ 
• Sydney’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• The Club: https://store.winner-intl.com/the-original-club-p2.aspx 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

1. We are testing a new The Transaction product - The Direct Deposit. The idea is to take something that happened that week and one host asks the other host 5 questions. The result is a 5 minute quick hit.
2. For this week's Direct Deposit, we cover RevFest. I'll give you the high level: 🐰 Jen Igartua and the Go Nimbly team killed it. Also, I am leading an unauthorized effort to rename it LoveFest 2026 but Matt Amundson keeps killing it. Lesss go!

 This is the first edition of The Direct Deposit presented by The Transaction.
========================================
Subscribe to the Newsletter: https://thetransaction.substack.com/ 

Follow the Show:

- Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ 
- Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/
- Sam's LinkedIn: https://www.linkedin.com/in/sam-guertin/ 
- The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ 
- The Transaction Website: https://thetransactionpod.com/ 

Ways to Tune In:

- Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz 
- Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 
- YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1 
- More Options: https://thetransactionpod.com/subscribe

Scott Albro is back in The Transaction hot seat—and he’s not here to play nice. Scott brings a flame-thrower to traditional playbooks, urging GTM leaders to experiment wildly, think like founders, and stop chasing MQLs like it’s still 2014.

Craig and Matt get Scott talking about everything from AI-driven storytelling to "vibe marketing," with detours through SDR history lessons, Red Bull stunts, and the existential crisis of printer ownership. If your go-to-market motion still depends on intent data and white papers… this episode might hurt (in a good way).

Also, Craig breaks his keyboard, Matt mentions a little company he likes to call Red Bull, and Producer Sam desperately attempts to curry favor with Scott.

Critical Takeaways

• The next wave of breakout companies will be driven by founders who embed themselves deeply into the Go-To-Market engine, not just product. Founder-led GTM creates authenticity, speed, and unmatched customer resonance.
• High-performing Go-To-Market teams in SaaS-land are shifting from one-size-fits-all playbooks to an experimentation mindset. It’s about making bold bets, measuring ruthlessly, and scaling what works, not chasing the hack of the week.
• Most so-called intent data is internet exhaust, not evidence of real purchase behavior.
• The best GTM orgs lead with narrative clarity, tying their solution to a broader shift in the world, anchoring it in customer pain, and delivering it with conviction. Skip this, and no one remembers you.
• Stunt marketing has a place in B2B SaaS. Think viral launches, bold storytelling, and emotional engagement. It’s not about gimmicks, it’s about being memorable in a world flooded with sameness.

Chapters

00:00 Episode Preview

03:30 – The Go-To-Market Founder Concept

07:00 – How Modern Go-To-Market Orgs Win

13:00 – Growth Bets: What They Are and Why They Matter for B2B Marketers

17:00 – Crafting a Resonant Story for your B2B brand

21:00 – Aligning Product and Go-To-Market Motions (Finally)

25:00 – Convincing B2B Startup CEOs to Experiment

30:00 – Bland’s Viral Growth and the “Stunt Marketing” Debate

36:00 – Storytelling Frameworks That Actually Work for Startups

42:00 – Lethal Weapon Posters and Swarms of Bees

Epic Quotes

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “If you're not reinventing your Go-To-Market org, you need to have a look in the mirror.” - Scott Albro
• “Founders can just do things that other people can't.” - Scott Albro

Connect with Scott

• LinkedIn: https://www.linkedin.com/in/scottalbro/ 

Shoutouts & Resources Mentioned

• Skosh: https://www.merriam-webster.com/dictionary/skosh 
• Skosh Usage over time: ​​https://books.google.com/ngrams/graph?content=skosh%2Csmidge%2Ctad%2Ciota%2Cmodicum%2Cwhit%2Cscruple%2Csmidgeon%2Cwee%2Cfathom&year_start=1800&year_end=2022&corpus=en&smoothing=3
• Bland
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• Tricia Gellman: https://www.linkedin.com/in/gellmansfmarketing/ 
•  Lena Waters: https://www.linkedin.com/in/lenawaters/

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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

Sign up for our Newsletter: https://thetransaction.substack.com/

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

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

B2B marketers keep making the same mistakes when it comes to events, only to end up asking why they didn’t see any ROI. Thankfully, we knew just the right person to help you improve your field marketing game…

Amy Holtzman is the Chief Marketing Officer of CHEQ, the leader in go-to-market security, and one of the best B2B marketing leaders in SaaS, especially when it comes to creating unforgettable experiences. Amy joins co-hosts Craig Rosenberg and Matt Amundson to explore how to plan an event marketing strategy that doesn’t suck, why you need to think beyond the vendor booth at a conference to see real ROI, and even how traditional paid search is holding up amidst the onslaught of AI advancements. 

Also, Craig says something he immediately regrets, Matt makes an unsettling insinuation, and Producer Sam calls someone a naughty word.

Critical Takeaways

• Events are still alive, if you are willing to put in the work to make them stand out. You can’t just “show up and hope.” Great booths need real strategy, creative hooks, and a human-first approach that makes people actually want to engage.
• Whether selling B2B or B2C, even strong demand dies in broken systems. Want revenue? Get your backend in order first so you can deliver remarkably good customer experiences
• Prospects are already using ChatGPT to build vendor shortlists. If your GTM doesn’t account for AI-powered discovery, you’re already behind.
• Despite the hype around AI, traditional paid search drove record enterprise deals for CHEQ in Q1 of this year, especially long-tail keywords. Don’t ditch the old toolbox just yet.

Chapters

00:00 - Episode Teaser

00:34 - Amy’s Amazing Hat, Chain Restaurant Pub Crawls, & the Apollo Theater

10:36 - Introducing Amy Holtzman, Chief Marketing Officer at CHEQ

13:46 - Lessons to Learn from the Worst Sales Experience Ever

25:53 - Search is Still Driving A Surprising Amount of Enterprise Deals

30:50 - Breaking Down the New G2 Research on B2B Buying Behavior & How AI is Impacting Vendor Shortlists

35:08 - How to Get More ROI from your Event Strategy & Field Marketing Mistakes to Avoid

39:46 - Sponsoring Niche Events can Pack a Massive Punch for Smaller B2B Brands

44:44 - Thinking Beyond the Booth When Planning out Your Event Strategy

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ Really strong quality work and great execution never goes out of style, no matter what the trend is and what's working.” - Amy Holtzman
• “If you want to sell things, make sure you have enough salespeople.” - Amy Holtzman
• “I rub the thing” - Craig Rosenberg

Connect with Amy

• LinkedIn: https://www.linkedin.com/in/aholtzman/ 
• Website: https://cheq.ai/ 

Shoutouts

• Every Little Step I Take by Bobby Brown: https://youtu.be/P0FKzPfsxA4?si=o3k9Iepu3KwnP1Aa 
• Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ 
• Jessica Lin: https://www.linkedin.com/in/jessicalin8/ 
• Amy’s Episode on The Drafting Table: https://www.thedraftingtablepodcast.com/content/conferences-arent-a-vibe-theyre-a-sales-channel-how-to-actually-make-them-worth-it-with-amy-holtzman-cmo-at-cheq 
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• G2 Buying Behavior Report: https://learn.g2.com/2025-g2-buyer-behavior-report
• Sydney Sloan: https://www.linkedin.com/in/sydsloan/ 
• Scott Albro: https://www.linkedin.com/in/scottalbro/ 
• The Tonga Room: https://www.fairmont-san-francisco.com/dine/tonga-room-hurricane-bar/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

AI use cases & tactics are moving at a million miles per hour which can make it hard to adopt some of these amazing innovations into your go-to-market strategy. Thankfully, we knew just the guy to have on the show to help us put into practice what otherwise could seem like technological mumbo, and or jumbo.

That man’s name is Jordan Crawford, the Founder of Blueprint GTM and one of the foremost go-to-market engineers innovating B2B sales and marketing on the cutting edge of AI advancements.

Jordan joins co-hosts Craig Rosenberg and Matt Amundson to dive into where we’re thinking about our go-to-market strategy and tech stack in the wrong way, how to segment cold outbound leads in an effective, yet scalable way based on pain, and how to evolve your revenue organization to excel in the new, ai-powered world.

Also, Craig shows off his sandwich shop shirt, Matt gets on yet another soapbox, and Producer Sam is asked for his opinion.

Critical Takeaways

• Identify specific, narrow segments by understanding unique heuristics that indicate a need for your product. For instance, identifying complex sales teams with high traffic who would benefit from LeanData's routing solutions is more effective than broad targeting.
• You need to understand your customers and their pain before bringing in tools like Clay or ZoomInfo. Sales leaders should spend time with SDRs to gain insights on what truly resonates with prospects, ensuring that any data or tools used are enhancing proven strategies rather than replacing deep understanding.
• The burden placed on SDRs to make sense of complex data without adequate support is a recurring issue. Leaders should simplify data insights and ensure SDRs are equipped with actionable, digestible information, alleviating stress and improving effectiveness. 
• Adopt a 'pain-qualified' segmentation approach. Identify segments that not only fit demographic profiles but also exhibit specific pain points that your product can address, such as complex routing needs in high-traffic sales teams for LeanData. This ensures messages are highly relevant and more likely to result in conversions.

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Introduction: The Intimidating Box

01:07 Mr. Pickles and Misadventures in Pocket Dialing

04:42 Craig’s Midlife Go-To-Market Crisis

05:31 What’s broken with the Old Go-To-Market Playbooks

07:30 What is The New World of Sales and AI

13:04 Segmenting and Targeting with Data

16:43 Permissionless Value Prop in Action

23:25 The List is the Message

25:47 Methodology and AI Integration

26:55 Understanding Customer Segments

29:56 Challenges in Sales and Marketing

33:18 Effective Campaign Strategies

35:16 Adapting to AI and Market Changes

38:37 Purpose of Niche Targeting and Success

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “The list is the message.” - Jordan Crawford
• “Never in my life has there been a more intimidating box than the ChatGPT, Claude, Gemini entry box because for the first time in our lifetimes, and maybe human history, we are the limiters.” - Jordan Crawford

New Terms

• Pain Qualified Segment: Two to five unique heuristics, often that imply tension.

Connect with Jordan

• LinkedIn: https://www.linkedin.com/in/jordancrawford/ 
• Website: https://blueprintgtm.com/ 
• YouTube: https://www.youtube.com/@BlueprintGTM 
• Jordan’s Latest Course: https://pvp.blueprintgtm.com/subscribe 

Shoutouts

• Scott Albro: https://www.linkedin.com/in/scottalbro/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved! 

Matt Heinz, the President of Heinz Marketing, is a top 50 Sales & Marketing Influencer and a prolific thought leader in the B2B marketing space. Matt digs into why B2B marketers should invest more in brand as the AI Age progresses, whether the Chief Marketing Officer should report to the Chief Revenue Officer, and why B2B marketers are so terrible at naming products and concepts.

Also, Craig ponders the meaning of parabolas, Matt ranks the best men’s hair in B2B Marketing, and Producer Sam gets confused by Craig talking about bats.

Critical Takeaways

• Develop a structured approach to AI adoption in Go-To-Market strategies. Instead of engaging in 'random acts of AI,' organizations should create an accountability chart detailing which jobs are better suited for machines and which require human intervention. 
• Personal connections and credibility can differentiate a brand in a noisy market. Efforts should be made to maintain and build these relationships alongside leveraging scalable technology.
• While marketing attribution is important, it should not solely focus on credit for past actions. It should be used to create a more predictable and reliable path towards future outcomes. Go to market teams need to look at attribution as a tool for driving the right behaviors and actions, rather than merely analyzing past performance.
• Signals, including “intent signals”, need to be understood in context and not treated as immediate leads. Revenue teams should use signals to inform their understanding of where a prospect is in the buying journey, rather than assuming all signals indicate readiness to buy. This nuanced understanding can improve targeting and engagement efforts.
• Even as AI and automation take on more tasks, creativity and strategic thinking remain irreplaceable. Teams should focus on leveraging AI for efficiency while reserving creative and complex problem-solving tasks for human talent. This balance can drive innovation and maintain a competitive edge.

Sponsored Segment

Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Episode preview

00:30 Craig Goes Batty and Some Auction Antics

04:13 Introducing Matt Heinz, President of Heinz Marketing

08:07 B2B Marketers are Terrible at Naming Concepts, Products, and Strategies

19:16 Should CMOs Report Up to CROs in B2B SaaS?

22:03 Ranking the Best Hair Amongst Men in B2B & Matt Confesses to Rocking a Mullet

27:27 How Go-To-Market Teams are Using AI & Evolving Their GTM Strategy with AI

37:13 Trust & Personal Relationships are Differentiators in the Age of AI Marketing Tools

42:11 The Role of Data & The Cloud Data Warehouse in B2B Marketing

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ We shouldn't be guessing anymore, we should be using the agents to tell us how to improve right away” - Matt Heinz
• “ If I have more noise and less time, who am I going to prioritize? It's the people I enjoy. It's the people I trust. It's the people I like. That's going to be a huge differentiator moving forward.” - Matt Heinz
• “ I don't want anybody to think that I'm not down with intent signals. I'm down with signals because right now the hardest thing in the world to do is engage.” - Craig Rosenberg
• “If you are looking for the solution in the tool, you're bound to fail.” - Matt Amundson

Connect with Matt Heinz

• LinkedIn: https://www.linkedin.com/in/mattheinz/ 
• Website: https://www.heinzmarketing.com/ 

Shoutouts

• Bat Tours in Austin: https://www.austintexas.org/things-to-do/outdoors/bat-watching/ 
• Bert Kreischer’s Raffle Story: https://youtu.be/EsCadHpBdkY?si=GDRoQpWQ9B1Z_55l 
• Coffee with Brent & Matt: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ 
• Joe Chernov: https://www.linkedin.com/in/jchernov/ 
• Steve Woods: 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 
• Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in 
• Lars Nilsson: https://www.linkedin.com/in/lanilsson/ 
• Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales 
• Ted Purcell: https://www.linkedin.com/in/tedpurcell/ 
• Adam Robinson: https://www.linkedin.com/in/adam-robinson-4b156810/ 
• Adam’s Episode: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal 
• Anthony Kennada: https://www.linkedin.com/in/akennada/ 
• Chris Walker: https://www.linkedin.com/in/chriswalker171/ 
• Scott Albro: https://www.linkedin.com/in/scottalbro/ 
• Mary Meeker: https://www.linkedin.com/in/mary-meeker-5823ba48/ 
• Simbe Robotics
• Mperativ
• Brent Adamson: https://www.linkedin.com/in/brentadamson/ 
• Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!