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The Transaction

The Transaction

Di: Craig Rosenberg & Matt Amundson | B2B Sales & Marketing Experts - Hosts of The Transaction
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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 B2B 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. Join our newsletter to get every episode + exclusive extras & insights right in your overcrowded inbox: https://thetransaction.substack.com/ 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. *This claim is entirely unsubstantiated and is made wholly based on the subjective judgment of the inherently biased people who are part of this show.The Transaction Economia
  • The GTM Plays AI Can’t Replace with David Politis, Host of Not Another CEO Podcast - Ep 86
    Oct 3 2026
    David Politis is the Host of the Not Another CEO Podcast, and previously led three industry-leading companies to successful acquisitions, including Vocalocity, Cloud Sherpas, and BetterCloud. David joins Co-Hosts Craig Rosenberg and Matt Amundson to discuss the business value of providing customers with truly unique experiences, why micro-segmenting your ICP can lead to better growth, and why the GTM Engineer is the highest-ROI individual hire in demand generation.Plus, David outlines why the “we'll build it ourselves” objection is a market signal, not a dead end.Also, Craig reveals he lost his wedding ring, Matt recounts watching a UFC from inside a 7/Eleven in the San Fernando Valley, and Producer Sam shares his feelings on the performance of the New York Rangers and San Jose Sharks. Critical TakeawaysTruly memorable in-person experiences earn access that ordinary campaigns cannot. A World Cup match, intimate chef-led dinner, or genuinely rare experience creates an unrivaled direct relationship with decision-makers. Remember, the relationship comes first; turning the event into a captive sales presentation kills that bond.The “we'll build it ourselves” objection is a market signal, not a dead end. One AI-native company serving sales engineers answered it with a microsite offering 14 free Claude skills behind a registration form. That move helps buyers experiment on their own while creating a natural path back to the vendor when security, complexity, and operational support become real requirements.Microsegmentation makes every downstream motion more relevant. Shrinking a 1,500-account ICP to a 200–300-account slice sharpens the outreach, content, demo, trial, and sales conversation at the same time. It also lets sellers master a small number of repeatable use cases instead of improvising across a hundred variations.A small roundtable can become a repeatable acquisition loop. Bring together a few leaders from the same microsegment, such as bank CIOs, extract the best anonymized insights, and use those findings to recruit the next cohort. Attendees gain peer intelligence they can take back to their companies, while SDRs and AEs gain outreach that sounds like it belongs in the buyer's world.Original data is one of the few content advantages AI cannot commoditize. For example, BetterCloud surveyed thousands of targeted business leaders each year and turned the results into a full year of content. Repeating a core set of questions for five or six years created trend data that appeared far beyond the original report.Talented, AI-first GTM engineers can build microsegmentation, data enrichment, customized decks, and supporting workflows at a pace traditional RevOps and marketing operations teams struggle to match. Leadership's job is to set the ICP and business objective, give the builder freedom to test, and move the winning experiments into the operating machinery.Chapters00:00 - Episode Preview02:02 - Introducing David Politis, Co-Founder, Not Another CEO05:17 - Selling SaaS to Companies Trying to Rip & Replace with Vibe-Coded Tools14:57 - The Business Impact of In-Person Events for B2B SaaS 22:25 - Microsegmenting Your ICP Improves Long-Term Growth30:32 - Matt Finally Decides To Show Up31:55 - How to Build Valuable Research Content that AI Can’t Replicate45:07 - Why GTM Engineers are the Highest ROI Roles to Hire ForJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ When you get people in the room, you can build relationships in a way that you cannot do virtually, you cannot do through automation.” - David PolitisConnect with DavidLinkedIn: https://www.linkedin.com/in/davidpolitis/ Not Another CEO Podcast: https://podcast.notanotherceo.com/ Not Another CEO Substack: https://notanotherceo.substack.com The StartUp Founder Survival Guide: https://www.linkedin.com/posts/davidpolitis_startup-founder-survival-guide-david-politis-activity-7158455968194875393-QVdh David’s Previous Episode: https://thetransaction.substack.com/p/narrow-down-your-damn-icp-with-david ShoutoutsScott AlbroRobert KoehlerTed PurcellAJ GandhiRory O’DriscollJon MillerChris OrlobNeil HarringtonLove the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    55 min
  • Win the AI Answer, Not Just the Citations with Tim Sanders, Chief Innovation Officer at G2 - Ep 85
    Sep 9 2026
    Tim Sanders is the Chief Innovation Officer at G2 and a New York Times best-selling author of five books, including Love is the Killer App and Dealstorming.Tim joins Co-Host Craig Rosenberg to discuss why "being cited" by ChatGPT and other LLMs means almost nothing compared to "winning the answer", which self-inflicted AI visibility mistakes that B2B marketers are making, and how to overcome the “Prompt Problem” by better understanding your customers.Also, Craig discusses his children’s taste in music, Matt is strangely absent, and Producer Sam briefly steers things down an extremely tactical rabbit hole for his own edification. Critical TakeawaysAudit every place you block AI crawlers, immediately. G2 blocked robot crawling for years before realizing the "big check" they thought they were protecting was worth less than the AI visibility they were sacrificing. Check every robots.txt block to see if the crawl-blocking upside actually outweighs the lost AI citation and recommendation value.Being cited by AI isn't the same as being recommended. In one example of asking an LLM for a product recommendation, Adobe was cited by the AI 13 times, but it did not make the final shortlist. Marketers should track whether their brand appears in the final "these are the three vendors" recommendation, not just whether they show up somewhere in the response.Unblock and re-platform gated content that models can't read. G2 learned models don't read PDFs or JavaScript-rendered pages during retrieval, only flat HTML. Audit your highest-value content (reports, comparison guides) and republish it in crawlable HTML instead of gated PDFs if AI visibility matters more than the lead-gen capture.Treat LLM relations as a new function, not a subset of SEO or PR. LLMs are now bigger influencers than traditional analysts. Because of this, G2, for example, explicitly unblocked Capterra, Software Advice, and GetApp after acquiring them from Gartner to capture this. GTM leaders should assign explicit ownership of "AI visibility" the way they already own analyst relations.Write answer-shaped content, not message-shaped content. Content structured as problem-solution-feature-benefit-CTA reads as "vendor speak" and lowers model confidence, while FAQ-style, conversational content that mirrors real Reddit-thread discussions earns more citations. Marketing teams should rewrite cornerstone content to directly resolve open questions in a natural, human tone rather than a sales pitch structure.Stop relying on web traffic as a north-star metric. With chat-driven buyers compressing research into a single prompt, overall website traffic will fall even as pipeline quality rises. Shift dashboards from sessions/pageviews to revenue attribution and closing ratio by traffic source.Chapters00:00 - Episode Preview03:11 - Introducing Tim Sanders, Chief Innovation Officer at G210:00 - Two Stories about Marketing Stunts and The World Series of Poker Finals19:01 - Answer Engine Optimization & Content Strategy in the AI Age26:32 - Optimizing Your YouTube Videos for AI LLMs to Index & Cite Your Content28:51 - Seeding Branded Content into Reddit to Influence the Outputs of LLMs36:59 - Does Your Company Website Still Matter in the AI Age? 43:58 - The Misaligned Prompt Problem Hurting Your Understanding of Customers & ProspectsJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“You have to get away from the addiction that traffic is a meaningful metric. It's not. Pipeline is the only metric that matters.” - Tim SandersConnect with TimLinkedIn: https://www.linkedin.com/in/sanderssays/ G2 Website: https://www.g2.com/ Love Is the Killer App by Tim Sanders: https://timsanders.com/love-is-the-killer-app/ Website: https://timsanders.com/ ShoutoutsOn The Edge by Nate Silver: https://www.penguinrandomhouse.com/books/529280/on-the-edge-by-nate-silver/ Josh Blyskal: https://www.linkedin.com/in/joshua-blyskal/ JH Scherck: https://www.linkedin.com/in/jhtscherck/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    51 min
  • How Founder POV Helps Sales Build Buyer Confidence with Jim Wilson, Partner at Costanoa Ventures - Ep 84
    Jul 21 2026
    Jim Wilson is an Operating Partner at Costanoa Ventures and cut his teeth leading global sales teams for decades at major companies including SumoLogic, Microsoft, Merced Systems, PTC, and NICE Systems. Jim joined Co-Hosts Craig Rosenberg and Matt Amundson to discuss the impact that strong Founder vision has on the sales team’s narrative, why paid POCs (Proof of Concepts) are making a comeback in B2B sales, and what truly sets B2B events apart for buyers.Plus, Jim examines why corporate gifting swag has gotten so bland while also providing some great examples from B2B brands that are doing it well.Also, Craig reads verbatim from the article of a past guest, Matt extolls the virtues of the loop-swoop-pull technique, and Producer Sam shouts out a fellow Sam.Critical TakeawaysDevelop and weaponize a strong founder point of view, and then cascade it to sales. The single biggest differentiator in a crowded market is a bold, opinionated narrative that challenges the status quo. Train sales reps to lead with a prescriptive point of view on how to evaluate your product. Rather than asking prospects "what do you want to do next?", top reps proactively outline a logical, step-by-step evaluation process. Top B2B sellers consistently become trusted advisors by doing this, which ultimately means they are invited to help prospects draft the RFP and frame competitors.B2B events are producing outsized pipeline, especially intimate dinners of 10–12 people. The key rule: no structured pitches, no selling at the event itself. Rather, use the event to learn where prospects went to school, what their kids are up to, and what makes them laugh; then follow up the next day with a warm, specific outreach.Implement paid, time-boxed POCs with both technical and business validation built in to validate not just technical fit but business ROI. Stop running open-ended "kick the tires" evaluations with no end date; set a timeline, assign a kickoff call, schedule the readout with decision-makers, and build a report that champions can use to get internal approvals.When it comes to effectively planning events and corporate gifting, GTM teams should ask: what does our buyer persona find genuinely interesting, and how do we build an experience around that?Chapters00:00 - Episode Preview02:25 - Introducing Jim Wilson, Partner at Costanoa Ventures05:57 - Why Creativity is Key to Effective Corporate Swag13:27 - A Disastrous First Encounter with a Bidet & Other Sleepy Sales Stories22:42 - How a Strong Founder POV Helps Sales Teams Build a Narrative33:36 - Events are Back as a Major GTM Channel 45:09 - Why Paid Proof of Concepts are Comin Back in B2B Sales CyclesJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ I love sales teams that have a strong point of view on how you should evaluate our product.” - Jim WilsonConnect with JimLinkedIn: https://www.linkedin.com/in/jimwilsonbayarea/ Costanoa Ventures Website: https://www.costanoa.vc/ ShoutoutsCarilu Dietrich: https://open.substack.com/pub/thetransaction/p/advisor-avengers-assembling-your Business Bricks: https://businessbricks.com/ Maria Boulden: https://open.substack.com/pub/thetransaction/p/steak-dinners-dont-close-deals-withSam McKenna: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge Brian Halligan: https://www.linkedin.com/in/brianhalligan/ Chris Orlob: https://open.substack.com/pub/thetransaction/p/solving-the-go-to-market-skills-crisis Scott Albro: https://open.substack.com/pub/thetransaction/p/founder-led-gtm-growth-bets-and-why David DMo Morse: https://www.linkedin.com/in/yodavidmorse/ Topline: https://substack.com/@toplinemedia Craig’s Article for Topline about Driving Demand: https://open.substack.com/pub/toplinemedia/p/343-open-rates-the-founder-led-fixOmar Akhtar: https://open.substack.com/pub/thetransaction/p/how-the-most-successful-b2b-marketing David Politis: https://open.substack.com/pub/thetransaction/p/narrow-down-your-damn-icp-with-davidJoe Sullivan: https://www.linkedin.com/in/joesu11ivan/  Robert Koehler: https://www.linkedin.com/in/rkoehler/ Bugcrowd: https://www.bugcrowd.com/ Feldera: https://www.feldera.com/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    56 min
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