The Transaction

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 Takeaways Truly 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. Chapters 00:00 - Episode Preview 02:02 - Introducing David Politis, Co-Founder, Not Another CEO 05:17 - Selling SaaS to Companies Trying to Rip & Replace with Vibe-Coded Tools 14:57 - The Business Impact of In-Person Events for B2B SaaS 22:25 - Microsegmenting Your ICP Improves Long-Term Growth 30:32 - Matt Finally Decides To Show Up 31:55 - How to Build Valuable Research Content that AI Can’t Replicate 45:07 - Why GTM Engineers are the Highest ROI Roles to Hire For Join 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 Politis Connect with David LinkedIn: 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 Shoutouts Scott Albro Robert Koehler Ted Purcell AJ Gandhi Rory O’Driscoll Jon Miller Chris Orlob Neil Harrington Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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 Takeaways Audit 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. Chapters 00:00 - Episode Preview 03:11 - Introducing Tim Sanders, Chief Innovation Officer at G2 10:00 - Two Stories about Marketing Stunts and The World Series of Poker Finals 19:01 - Answer Engine Optimization & Content Strategy in the AI Age 26:32 - Optimizing Your YouTube Videos for AI LLMs to Index & Cite Your Content 28:51 - Seeding Branded Content into Reddit to Influence the Outputs of LLMs 36:59 - Does Your Company Website Still Matter in the AI Age? 43:58 - The Misaligned Prompt Problem Hurting Your Understanding of Customers & Prospects Join 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 Sanders Connect with Tim LinkedIn: 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/ Shoutouts On 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!

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 Takeaways Develop 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? Chapters 00:00 - Episode Preview 02:25 - Introducing Jim Wilson, Partner at Costanoa Ventures 05:57 - Why Creativity is Key to Effective Corporate Swag 13:27 - A Disastrous First Encounter with a Bidet & Other Sleepy Sales Stories 22:42 - How a Strong Founder POV Helps Sales Teams Build a Narrative 33:36 - Events are Back as a Major GTM Channel 45:09 - Why Paid Proof of Concepts are Comin Back in B2B Sales Cycles Join 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 Wilson Connect with Jim LinkedIn: https://www.linkedin.com/in/jimwilsonbayarea/ Costanoa Ventures Website: https://www.costanoa.vc/ Shoutouts Carilu 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-with Sam 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-fix Omar 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-david Joe 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!

Carilu Dietrich & Maya Spivak joined Craig, Matt, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording where they shared insights on building founder and executive organic social media as a primary demand channel, why startups need to develop speed as a marketing skill, and why going viral on social doesn’t amount to what it seem for B2B companies. Carilu is the author of the Hypergrowth Leadership SubStack and is an all-star advisor and startup marketing leader. Maya is the Founder & Chief Marketer of Marketing.fan, a brand and creative marketing agency, and former VP of Marketing at Gretel.ai and Mux. Critical Takeaways Invest in taste, or find someone who has it, before spending on out-of-home ad campaigns. Out-of-home advertising in major markets is constrained supply with non-trivial costs, and a mediocre creative execution wastes every dollar and actively damages brand perception at scale. Before committing budget to OOH, have someone with genuine creative discernment review the work, and if that person doesn't exist in-house, find them in your network before the media buy clears. Consistency beats virality for pipeline generation. Marketing teams should resist chasing one-off viral brand moments and instead build sustainable content cadences. Allocate budget and headcount to rhythm, not lottery tickets. Real differentiation for brands is about timing and originality, not just quality. The frameworks your competitors are copying right now are already losing their edge, and the window to do something genuinely surprising is always narrower than it seems. The pace of AI innovation and product development means that GTM leaders need to operationalize speed as a marketing capability. GTM teams need pre-built rapid-response playbooks for product launches, because the window to capitalize on a launch is now measured in hours, not weeks. For example, Carilu's product marketing team had 32 hours notice from OpenAI before a major LLM launch and shipped a full campaign within that window. Teams that don't have templates, approval chains, and asset libraries ready in advance will consistently miss the moment when momentum is highest. Edutainment is the new table stakes for B2B events, content, and advertising. Marketing teams should interrogate every content format and event experience against the question: is this entertaining enough to earn attention before it earns trust? Chapters 00:00 Episode Preview 00:50 Introducing Carilu Dietrich & Maya Spivak 03:04 Are Viral Moments Worth Chasing for B2B Brands 12:02 Real Market Momentum Starts with Product 13:48 Edutainment Marketing Wins 14:12 Building Out Bold Billboards Campaigns for B2B Brands 16:29 Copycats and What Not to Do 17:52 Examples of Marketing Creativity Beyond Billboards 20:12 Startup Founder Social Media Playbook for B2B 23:19 LinkedIn Organic Content Marketing Drives Enterprise Revenue 27:29 Amplifying Customer Stories That Work 31:26 Zig When Others Zag 33:50 When B2B Brands Should Involve Influencers & The Need for Fast Launches 37:49 Out Of Home Advertising Taste is Critical Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/ Epic Quotes “The real problem that earlier stage companies have is they don't need advice. They need be able to do the work.” - Carilu Dietrich “If you're gonna spend the money, do it right. Make sure you have some taste.” - Maya Spivak Connect with Carilu LinkedIn: https://www.linkedin.com/in/cariludietrich/ Carilu’s SubStack: https://www.carilu.com/ Carilu’s Past Episode: https://open.substack.com/pub/thetransaction/p/advisor-avengers-assembling-your Connect with Maya LinkedIn: https://www.linkedin.com/in/mayagrinbergspivak/ Marketing.fan Website: https://www.marketing.fan/ Shoutouts GTMshift: https://gtmshift.com/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Dan Kimball is a GTM Advisor, AI Architect, and independent consultant at The Operating Partnership LLC. Dan’s a marketing expert with a bevy of amazing experiences to draw on, from serving as CMO of Spectrum Equity and ThisMoment, to VP of Marketing at Yelp, and SVP of Global Marketing at Eventbrite. Dan joins co-hosts Craig Rosenberg and Matt Amundson to dive into what sets great B2B brands apart and why marketers need to look at some of their metrics with a lot more scrutiny. Plus, Dan shares what happened when he unknowingly offended half of Cape Cod with a radio ad. Also, Craig pitches his idea for a nautically themed vape shop, Matt compares to Dan to M. Night Shyamalan, and Producer Sam slightly misquotes an iconic Steve Buscemi line. Critical Takeaways ICP clarity is the single highest-leverage activity a GTM team can do this year. The amount of focus a company has on its Ideal Customer Profile is "highly correlated with success at driving bookings goals." GTM leaders should run a formal ICP project at the start of every year, not treat it as a one-time setup task. The tools and AI capabilities now exist to make this faster and more rigorous than ever. Look at marginal ROAS (the return on the last incremental dollar spent in the Google auction) rather than blended ROAS. Mixed media modeling (MMM) is now accessible to mid-market companies, and B2B marketers should deploy it before their next budget cycle. Mid-size B2B companies can access credible MMM vendors and get marketing attribution sophistication that far exceeds what Google Analytics or any last-touch model can provide. Marketing leaders should bring a vendor comparison to their next QBR and frame it as risk mitigation: the current attribution model is actively misleading budget allocation decisions. As ChatGPT eats into Google organic traffic, brands increase paid search spend to compensate, which inflates CPCs for everyone, which degrades LTV-to-CAC ratios across the board. B2B marketing leaders should model what their blended CAC looks like if CPCs increase 20-30% and build the case for upper-funnel diversification (EG: YouTube, CTV, LinkedIn, organic community) before the CFO forces the conversation. Chapters 00:00 - Episode Preview 02:41 - Introducing Dan Kimball, GTM Advisor and Consultant at The Operating Partnership LLC 08:38 - The Unintended Consequences of Naming a Company Or, Dan Gives Us The Skinny on a Boneheaded Brand Name 17:44 - What's in a Name (Of a Company, Brand, or Product)? 25:59 - Why Your Degree of ICP Focus is Directly Correlated to Business Success 41:39 - B2B Marketers Need to Scrutinize Their Marketing Attribution More Thoroughly 48:05 - Diversify Paid Channel Spending Beyond Just Google or Facebook Owned Channels Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/ Epic Quotes “People aren't putting as much scrutiny on marketing attribution as they should. And this is nothing new, but people are giving way too much credit to Google” - Dan Kimball “ Look, I listen to it. I'm down.” - Craig Rosenberg, 2026 “You're not down. You're not down if you said you're down.” - Dan Kimball “You might be up.” - Matt Amundson Connect with Dan LinkedIn: https://www.linkedin.com/in/danielkimball/ Shoutouts Kara Swisher Love the show? Give us a shoutout on LinkedIn and tell us what you loved!