The Transaction

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 TakeawaysInstead 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.Chapters00:00 Episode Preview03:30 The GTM Midlife Crisis Hits – Why the old playbooks stopped working06:15 Building a New Playbook with AI in the Go-To-Market Hacker era08:45 Matt’s AI Buyer Persona Workflow – How to build and deploy AI agents for feedback13:15 Talk to Your AI Tools Like People 17:00 999/1000 Accuracy Rate – Why AI is now a mission-critical content editor25:30 Account Research is the New Minimum – How GTM teams are winning with better prep30:00  Matt & Craig just Want to Watch the World Burn37:00 Events Are Back, Baby – People crave new insights and in-person energy40:00 LinkedIn has changed, but it is still the social platform of choice for B2B brands45:00 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 himSign 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 AmundsonShoutoutsMaria 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 SaaStrMark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ Copy.aiKlarity: 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=falseLove 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 TakeawaysEvents 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 experiencesProspects 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.Chapters00:00 - Episode Teaser00:34 - Amy’s Amazing Hat, Chain Restaurant Pub Crawls, & the Apollo Theater10:36 - Introducing Amy Holtzman, Chief Marketing Officer at CHEQ13:46 - Lessons to Learn from the Worst Sales Experience Ever25:53 - Search is Still Driving A Surprising Amount of Enterprise Deals30:50 - Breaking Down the New G2 Research on B2B Buying Behavior & How AI is Impacting Vendor Shortlists35:08 - How to Get More ROI from your Event Strategy & Field Marketing Mistakes to Avoid39:46 - Sponsoring Niche Events can Pack a Massive Punch for Smaller B2B Brands44:44 - Thinking Beyond the Booth When Planning out Your Event StrategySign 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 RosenbergConnect with AmyLinkedIn: https://www.linkedin.com/in/aholtzman/ Website: https://cheq.ai/ ShoutoutsEvery 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-reportSydney 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!

Jordan Crawford, the Founder of Blueprint GTM and a pioneer in B2B sales innovation, joins Craig Rosenberg and Matt Amundson for an enlightening discussion. They tackle the rapid evolution of go-to-market strategies, emphasizing the need to adapt amidst technological advancements. Jordan shares tactics for effective lead segmentation based on customer pain points and highlights the importance of understanding your audience before deploying AI tools. With fresh insights, they critique traditional sales methods and explore how to refine messaging through intentional problem-solving.

Matt Heinz, President of Heinz Marketing and a top 50 Sales & Marketing Influencer, shares insights on navigating AI in B2B marketing. He emphasizes the critical need for structured AI adoption in go-to-market strategies, moving beyond 'random acts of AI.' Matt discusses the importance of personal connections in a noisy market and critiques the tendency of marketers to misname products. Additionally, he explores the evolving relationship between marketing and sales leadership, proposing a shift in reporting dynamics for CMOs.

Lars Nilsson, Founder and CEO of SalesSource and former VP of Global Sales Development at Snowflake, shares his expertise in B2B sales development. He discusses the evolution of sales strategies in SaaS, highlighting the need for empowerment and recognition of Sales Development Representatives. Lars also explores the emerging role of go-to-market engineers and the innovative use of AI in sales training. The conversation underscores the importance of continuous learning and effective marketing strategies for boosting revenue and improving customer interactions.

Most B2B brands (yes, probably yours) think that they’re ‘customer-centric’, and yet none of them ever stop droning on and on about their product and its ‘revolutionary’ features.Lauren Goldstein is the Chief Growth Officer of Winning by Design and Co-Founder, Board Member, Chair of the Board of Directors for Women in Revenue. Lauren joins co-hosts Craig Rosenberg and Matt Amundson to chat how B2B sellers and marketers can connect with buyers in the way buyers want them to, why having a diverse leadership team is an invaluable asset for any startup, and why “Strategic RevOps” is enabling breakthrough growth for SaaS startups.Also, Craig shocks the world by caping for his portfolio companies’ sales pitches, and Matt mentions the production design aesthetic of a niche director.Critical TakeawaysImplement structured mentorship programs in your org where experienced team members can guide less experienced colleagues, as this can lead to increased job satisfaction and retention, on top of the personal and professional development of your whole team.Instead of spending time on a sales call waxing poetic about the ‘revolutionary’ features of your product, use that time to ask your prospect what success looks like for them. How are they measured as a success or failure? Uncover that ideal state and help them understand how your product can get them there, provided it actually can; otherwise, don’t waste their time and yours.Consider using ‘Reverse Demos’, where instead of showing off your product right away, you have the customer outline their current processes and challenges. While this approach might not work with all types of buyers, it could be effective in understanding complex systems and better tailoring your pitch to the customer's actual needs.Cross-functional alignment across your go-to-market team is crucial. Sales, marketing, product, and finance teams need to work collaboratively, understanding each other’s objectives and challenges. Regular inter-department meetings to align goals and strategies help everyone move in the same direction towards shared business goals.Companies that have strategic RevOps roles are better at aligning their sales and marketing efforts with financial and operational goals, ultimately driving growth and operational efficiency.Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Episode Preview00:30 - Are the Angels a Real Team & Breaking Down the Backgrounds03:24 - Introducing Lauren Goldstein, Chief Growth Officer of Winning By Design & Co-Founder of Women in Revenue06:36 - The Origin Story of Women in Revenue (The group, not the concept)18:17 - The Immutable Impact Diverse Teams in Business23:43 - B2B Tech Brands Are NOT Connecting Buyers in the Ways That SaaS Buyers Want31:39 - What is a ‘Reverse Demo’ & Why is Gartner Analyst Dan Gottlieb Recommending it36:00 - Revenue Growth in SaaS Comes Back to Identifying the Right Buyers40:43 - The Critical Role of Rev Ops in B2B Go-to-Market Strategy for SaaS44:00 - Strategic Rev Ops: The Key to Integration & Go-To-Market AlignmentSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Managing multiple stakeholders in an enterprise sale is not a new thing. But it's more than managing multiple stakeholders, it's really about helping to facilitate a conversation where they're all understanding the problem in the same way and can connect back to a common denominator.” - Lauren Goldstein“ There is no greater liar as a buyer, than a marketer.” - Matt Amundson (A Marketer)Connect with LaurenLinkedIn: https://www.linkedin.com/in/laurengoldstein/ Winning by Design Website: https://winningbydesign.com/ Women in Revenue Website: https://womeninrevenue.org/ ShoutoutsSydney Sloan: https://www.linkedin.com/in/sydsloan/ Sydney’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with Katharine Reagan: https://www.linkedin.com/in/katharine-reagan/ Shari Johnston: https://www.linkedin.com/in/sharijohnston/ Jen Dimas: https://www.linkedin.com/in/jenpd/ Tracy Eiler: https://www.linkedin.com/in/tracyeiler/ Jim Walker: https://www.linkedin.com/in/jwwalker/ Robert Koehler: https://www.linkedin.com/in/rkoehler/ RadiusMarketoMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ InsideViewBabcock JenkinsDan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan’s Episode: ​​https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb MiroMark Kosoglow: https://www.linkedin.com/in/mkosoglow/ Mark’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity Kelly DeHart: https://www.linkedin.com/in/kelly-dehart-18b63315/ Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Colin Gerber: https://www.linkedin.com/in/colinsgerber/ SocureAdam B. Needles: https://www.linkedin.com/in/abneedles/ Adam’s Episode: https://open.substack.com/pub/thetransaction/p/the-new-go-to-market-blueprint-with AnnuitasLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

Ana Leyva advises early-stage startups at Pear VC on their go-to-market strategy to help them build stunning sales motions that set them up to scale. Ana provides pre-seed and seed startups with her first-hand experience as a seasoned operator with past roles at tech unicorns Box, ServiceTitan, and Vanta. Ana joins Co-Hosts Craig Rosenberg and Matt Amundson to delve into how to transition beyond a founder-led sales motion without losing their special perspective, why insight-driven outreach beats crappy sales personalization in B2B, and the two foundational pillars that you need to have in place to build a strong go-to-market strategy.Additionally, Ana details the importance for founders to be extremely disciplined with their Ideal Customer Profile and who they allow to steer the course of the future of their company.Also, Craig gets a ton of text notifications, and Matt muses about buying Craig a present for Easter.Critical TakeawaysThe crappy bit of personalization you grabbed from LinkedIn and added to your stale cold outbound email is not going to set you apart. ‘We went to the same school’ doesn’t help that decision maker develop a solution to the problems they’re facing.Rather than relying on bare-minimum ‘personalization’, put your thinking cap on and reach out with a business insight that can actually help your prospect learn more about their business, understand their problem better, or make a more informed decision.As hard as it can seem to turn down customers early on, founders need the discipline to focus on prospects who will truly benefit from their product, and saying no to the wrong fit is crucial for building long-term customer relationships.The bedrock of your go to market strategy should be built upon endless customer obsession and very strict ICP (Ideal Customer Profile) parameters. That ensures you deeply understand the pain your customer solves and can build a product to solve that pain effectively. Don’t just let your customers come to you, you need to pick the right protagonists for the epic narrative that you are creating for yourself and your customers. Be picky about who you allow to join and steer the arc of this grand story you are embarking on. Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Episode Preview00:20 - Squishy Pineapples & The 1995 UCLA Bruins04:01 - Introducing Ana Leyva, GTM Leader at Pear VC08:29 Selling at B2B Conferences on the Road as a New Mom 11:32 - Focus on Providing Value, not on Bland “Personalization”21:33 - B2B SaaS Founders Need to Rewrite New Go To Market Playbooks27:24 - Scaling Your Sales Team & Shifting from Founder-led Sales34:53 - Discipline is a Founder’s Best Friend & Going Narrow is the Way to Win as a Startup45:06 - Is Cold-Calling Coming back in Style for SaaS Sales Teams?Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“I am sick of personalized emails.” - Ana Leyva“I always tell our founders, you’re not selling for the initial close; you’re selling for the renewal.” - Ana LeyvaConnect with AnaLinkedIn: https://www.linkedin.com/in/analeyva/ Pear VC Website: https://pear.vc/ ShoutoutsAJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ Brandon Redlinger: https://www.linkedin.com/in/brandonredlinger/ Brent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’s Episode: Jen Allen-Knuth: https://www.linkedin.com/in/demandjen1/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Jason’s Post on LinkedIn: https://www.linkedin.com/posts/jasonmlemkin_so-theres-a-lot-of-angst-on-linkedin-about-activity-7308223252420509697-EJCSStevie Case: https://www.linkedin.com/in/steviecase/ Scott Albro: https://www.linkedin.com/in/scottalbro/ GongScott Barker: https://www.linkedin.com/in/ssbarker/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Sheila Stafford, Founder and CEO of TeamSense, dives into the essentials of landing enterprise clients as a startup. She emphasizes that Net Revenue Retention is the key metric for success, highlighting the importance of customer satisfaction as a business moat. Sheila discusses the decline of email as a sales tool and her preference for modern PR strategies. Moreover, she shares insights on the significance of domain expertise and the need to address operational pain points in staffing to boost productivity, making her insights invaluable for new founders.

Eric Spett, Founder and CEO of Scalebound, shares insights on sustainable growth for CEOs. He emphasizes the importance of focusing on your primary go-to-market channel rather than spreading resources too thin. Eric discusses the pitfalls of 'shiny object syndrome' and the value of sticking with proven strategies. The conversation also dives into the significance of in-person events and community engagement, offering humorous anecdotes and personal experiences that highlight the power of authentic connections in business.

Sam McKenna, Founder of SamSales Consulting and a leading expert in social selling, joins the hosts for a lively discussion. They tackle the importance of personalization in prospecting and share tips on engaging with potential clients authentically on LinkedIn. Sam emphasizes standing out by adding thoughtful comments rather than generic interactions. The conversation also touches on the evolution of go-to-market strategies and the balance between automation and personal touch in sales, with amusing stories sprinkled throughout.