The Transaction
The Transaction

The Transaction

Craig Rosenberg & Matt Amundson | B2B Sales & Marketing Experts - Hosts of The Transaction

Overview
Episodes

Details

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.

Recent Episodes

The AEO Playbook: Own the AI Shortlist - Live with Sydney Sloan at GTM Tailwinds - Ep 80
JUN 8, 2026
The AEO Playbook: Own the AI Shortlist - Live with Sydney Sloan at GTM Tailwinds - Ep 80
Sydney Sloan, the CMO of G2, joined Craig, Matt, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording where she outlined the major shift in B2B buyer behavior, how to measure and track Answer Engine Optimization, and why the partnership and distribution layer is as important as content creation.Critical TakeawaysOver half of B2B buyers (51%, up from 24% just one year ago) now start their research in an LLM rather than Google. GTM leaders must treat AI answer engines as the new top-of-funnel, not a novelty. Waiting another year means your competitors get a 12-month head start on owning these answers.Stop writing for search crawlers, instead write for the person you're trying to influence. The old HubSpot model of casting a wide content net (writing for non-marketers to drive traffic) is losing effectiveness. Instead, teams should map out the specific jobs-to-be-done for each buyer persona, the product leader, the CFO, the practitioner, and write questions and answers directly for that person. This persona-centric content approach is what gets surfaced and cited in LLM responses.LLMs favor content that mirrors the structure of a question, such as FAQs, pro/con lists, pricing comparisons, and definitional formats. G2 proactively added pricing data and pro/con lists to every product profile after seeing those formats show up in prompt patterns six months earlier. GTM teams should audit their top-performing SEO pages and rewrite AEO versions with this structure immediately.Publications like Forbes and VentureBeat are now formal citation sources for LLMs. G2 counter-pitched a negative MIT AI study and earned significant coverage, which then got indexed and cited. Teams should re-engage PR agencies (if they have newsworthy content) and consider low-cost options like Forbes Council ($1,600/year) to establish founder brand as authenticated content on authoritative domains.Chapters00:00 Episode Preview00:42 Introducing Sydney Sloan, the CMO of G201:25 Focus Wins at SalesLoft03:01 AEO vs GEO Explained04:00 New Buyer Research Behavior05:18 Build Brand in LLMs06:44 AI Citations of Reddit and G209:30 Zero to One AEO Setup10:10 Content Engineering Playbook11:58 G2 Adapts to Prompt Trends13:50 Measuring AEO Impact17:29 Consensus Signals and Sentiment19:37 Bots vs Humans Traffic20:14 Own Citation Sources21:07 Reddit and Influencers22:32 Freshness vs Old Content23:51 Pruning Content for LLMs25:01 PR Is Cool Again in B2B Marketing27:02 Should Founders Hire PR28:57 Partnerships and Frenemies33:07 AEO and SEO Together34:40 LinkedIn Virality Tips35:43 Wrap Up and OutroJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“AI's changed everything. Including where your buyers go to do their research, discovery, and shortlisting.” - Sydney SloanConnect with Sydney SloanLinkedIn: https://www.linkedin.com/in/sydsloan/ G2 Website: https://www.g2.com/ ShoutoutsGTMshift: https://gtmshift.com/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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36 MIN
Attention is the New Moat - LIVE with Scott Albro at GTM Tailwinds - Ep 79
MAY 31, 2026
Attention is the New Moat - LIVE with Scott Albro at GTM Tailwinds - Ep 79
The one and only Scott Albro once again returns to The Transaction, but this time, Scott joined Craig, Matt, James Kaikis, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording. Scott shares his insights on how to overcome the real GTM problem of the ‘attention bottleneck’ and lays out a precise framework for flipping from push to pull using network thinking, transformation narratives, and high-leverage distribution tactics. Using real examples from Clay, Granola, and ServiceTitan, he shows exactly how to identify 10x hubs in your market, build a narrative that makes your customer the hero, and develop a founder brand strategy that creates category synonymy rather than LinkedIn vanity metrics.Critical TakeawaysJust because you start a company, doesn’t mean anyone cares about it. GTM strategy has to start with the question, “How will this company earn attention in a market where AI has made product-building and content creation cheaper than ever?”GTM leaders should map their market as a network to identify the "10x hubs" in their market, which are nodes that have outsized influence over target buyers, and deliberately influence those hubs with their narrative. This unlocks massive downstream reach that a standard approach to a target account list would not have surfaced.Every startup needs three story types: the customer story (pain + day-in-life), the personal journey story (founder authenticity), and most importantly, the transformation story. The transformation narrative has three parts: the broken status quo, a believable-but-magical future vision, and a prescriptive guide for how customers get there.A narrative must be big, differentiated, and believable simultaneously. Scott's three non-negotiable attributes for a winning narrative are that it must compete for attention in your specific market, it must say something nobody else is saying, and it must be proven in the product demo. Marketers should test every narrative draft against all three filters before taking it to market.Chapters00:00 - Session Preview Clip00:40 - Introducing Scott Albro & How Scott’s First Board Meeting with Craig Went04:58 - Why the Attention Bottleneck is a Crisis for Startups in an Ever-Crowded Market 11:22 - How B2B Marketers Craft Winning Narratives That Spread Like Wildfire16:16 - Focusing Closer on Your Target Market Will Reveal The Compelling Narrative That Works For Your Buyer20:41 - Why & How Founders & CEOs Should Incorporate Their Own Authenticity into Their Narrative26:49 - Treating Your Market as a Network of Target Accounts, Not Just a Target Account List32:11 - Creating Systems for Founders and CEOs to Build Attention Around Your Brand NarrativeJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ In today's market, everything is downstream of attention.”  - Scott Albro“The default setting for a startup is obscurity.” - Scott AlbroConnect with ScottLinkedIn: https://www.linkedin.com/in/scottalbro/ ShoutoutsGTMshift: https://gtmshift.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Gainsight: https://www.gainsight.com/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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36 MIN
Building an Incorruptible Company that Lasts with Eric Ries, Author of Incorruptible & The Lean Startup - Ep 78
MAY 27, 2026
Building an Incorruptible Company that Lasts with Eric Ries, Author of Incorruptible & The Lean Startup - Ep 78
It’s not every day that you get to have one of the most important thinkers in the startup world on your podcast, but for The Transaction, that day is today.Eric Ries is a Founder and the renowned business author of The Lean Startup and his brand new book, Incorruptible: Why Good Companies Go Bad…and How Great Companies Stay Great.Eric joins Craig Rosenberg and returning guest host Scott Albro to discuss the forces that make companies vulnerable to destruction from within and without. Then he offers solutions that safeguard against them for the long-term.Incorruptible is the blueprint for companies that will prosper and endure without losing their soul. Plus, Eric shares how go-to-market teams, in their unique market-facing position, can make a profound impact on customer trust, both positively or negatively.Also, Craig describes his current deodorant situation, Scott mentioned the looming ARR creative accounting crisis, and Producer Sam mentions the link to Eric’s book in the show notes below. Critical TakeawaysTrust is the force that lowers friction, reduces costs, increases velocity, and makes customers stick around even when a company makes mistakes. By keeping their promises to customers, sales and marketing teams create long-term enterprise value by adding to the company’s trust account.A strong customer promise is not enough unless a company’s incentives, reporting, governance, and business model are built to defend it and deliver value to the customer.Corruption often looks like optimization in the moment. Eric defines corruption as “the making of money without the creation of value,” which many ‘best practices’ often encourage. Overpromising product capabilities, manipulating ARR, squeezing customer trust for quota, or turning a beloved product into an ad-clogged mess may improve a metric temporarily, but it destroys the value engine underneath.Go-to-market sits at the edge of the company’s moral logic. The GTM team is the “pointiest point at the edge of the spear” because it’s how the market experiences the company’s promises first. For example, revenue leaders are not just responsible for pipeline; they are responsible for making sure the promises used to create pipeline are believable, durable, and backed by the product and business model.Corporate governance is not about extra busywork or bureaucracy; it’s how companies, yes, even startups, protect what makes them worth building.Chapters00:00 - Episode Preview02:25 - Introducing Eric Ries, Author of The Lean Startup & Incorruptible06:09 - The Legacy of The Lean Startup in the AI Age08:59 - The Business Lessons Learned from Sol Price’s Journey of Founding FedMart & Price Club18:39 - How Founding The Long-Term Stock Exchange Showed The Limits of Best Practices & Conventional Thinking24:03 - How Businesses Cash in Trust & How They Build Trust with Customers27:54 - Why Re-examining OKRs & GTM Metrics Can Improve the Long-Term Health of a Company35:06 - The Looming Crisis in How Startups are Accounting their Annual Recurring Revenue (ARR) 40:10 - Why & When Early Stage Startups Need To Seriously Think About GovernanceJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ Trust is the asset that compounds.” - Eric Ries“ A lot of these so-called best practices are actually value destroying.” - Eric RiesConnect with Eric LinkedIn: https://www.linkedin.com/in/eries/ Incorruptible on Amazon: https://www.amazon.com/Incorruptible-Shape-Companies-That-Stand/dp/B0FWZZBPZB Website: http://incorruptible.co ShoutoutsLenny’s Podcast: https://www.lennysnewsletter.com/podcast Matt Dixon: https://www.linkedin.com/in/matthewxdixon/ Brent Adamson: https://www.linkedin.com/in/brentadamson/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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44 MIN
Using AI to Empower SDRs & Eliminate Admin Work with David Wilkins, Founder of SDR Leaders of EMEA & B2B Sales Expert - Ep 77
APR 16, 2026
Using AI to Empower SDRs & Eliminate Admin Work with David Wilkins, Founder of SDR Leaders of EMEA & B2B Sales Expert - Ep 77
Excessive admin work and poor-performing sales plays are killing SDR effectiveness and, in turn, company growth. We just so happen to know just the B2B sales expert to help SDR leaders kick things up a notch, wherever they may reside around the globe.Besides having a wonderful British accent, which Craig loved, David Wilkins is the Founder of SDR Leaders of EMEA and the Co-Founder of SDR Leaders of USA and APAC. David joins Co-Hosts Craig Rosenberg and Matt Amundson to dig into how sales leaders are overcoming the major issues facing SDRs (Sales Development Reps) in B2B sales today. David shares how successful sales leaders are implementing AI tools to cut down on excess admin work for their SDRs, why sales channels like cold-calling & video messages are outperforming email outreach, and how dialing up the difficulty of the sales training for your reps can keep them cool as can be on even their most cantankerous sales calls.Plus, David outlines the totally standard, run-of-the-mill journey of how he went from studying at the second-worst university in the UK to working for the number-one mayonnaise manufacturer in the Netherlands and ended up getting into B2B sales. Also, Craig references a late-80s rap duo, Matt alludes to the promise of a brisket, and Producer Sam somehow manages to ask a decent salestech question after breaking the 4th wall earlier in the episode.Critical TakeawaysExcessive admin work is still eating the SDR role alive. In a surprising number of B2B companies, SDRs are still burning three-plus hours a day on manual admin tasks. That is not harmless busywork in B2B sales; it is precious selling time being quietly set on fire. Rather than replacing a human SDR with an AI avatar, target this admin & sales prep work for elimination with AI. Email-first outbound has run out of runway. Email still has a place, but it should be just one piece of a larger outbound strategy that focuses more heavily on better-performing tactics like cold calls and social media touchpoints. The practical implication for sales and marketing leaders is simple: email can support the motion, but it cannot be the whole motion anymore.Sending videos and voice notes through LinkedIn messages works because they do something most outreach still does not: they make it obvious a real, honest-to-goodness human being is on the other end. That is especially useful in B2B SaaS, where copy-paste messages have saturated email, text, and even DM inboxes, and being able to interrupt that pattern buys sellers the few seconds of attention they need to make inroads.The sales training you provide for your SDRs and AEs should be significantly harder than anything they might deal with on a standard sales call. That way, if they find themselves in a delicate situation, they have the skills to stay calm and continue moving the conversation forward. A great way to give your sales reps more, well, reps is to use a training tool with AI-avatars of different customer profiles in sales scenarios.Chapters00:00 - Episode Preview00:51 - Trans-Atlantic Holiday Customs and Re-Ranking of Meats 04:11 - Introducing David Wilkins, Founder of SDR Leaders of EMEA & B2B Sales Expert06:55 - David's Journey From a Terrible School to Amazing Mayo & Eventually a B2B Sales Job15:10 - Why SDR Leaders Don't See Headcount as The Solution for Success with Sales Development in B2B SaaS 30:18 - Why Cold-calling Beats Email for Engaging with Prospects34:59 - Video Messages & Voice Notes Break the Pattern of B2B Sales Outreach46:09 - Improving Sales Training with AI Avatars To Help SDRs Perform Better on Sales Calls49: 57 - Predicting the Future Evolution of the SDR Role in B2B Sales & GTM55:04 - Random Rap & Wrestling References Before Wrapping UpJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ Make the training harder than the game.” - David Wilkins“ Making this function what it is, which is a critical part of the revenue generating organization.” - David Wilkins“ I'm gonna be calling myself Ron now, if ever I get in trouble” - Ron DavidsonConnect with DavidLinkedIn: https://www.linkedin.com/in/daveewilkins/ SDR Leaders of EMEA Website: https://sdr-leader.com/ ShoutoutsLars Nilsson: https://www.linkedin.com/in/lanilsson/ Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales?utm_campaign=post-expanded-share&utm_medium=web Travis Henry: https://www.linkedin.com/in/travisjhenry/ Russell Hearl: https://www.linkedin.com/in/russhearl/ PG.aiTitanXNooksHiya Morgan Ingram: https://www.linkedin.com/in/morganjingramamp/ QuibblySynthesiaTavusHyperboundScott AlbroRodney-O & Joe Cooley: https://youtu.be/BynWb6swQ74?si=_7ykfGXyz0GDACRl Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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58 MIN
Building a Movement Through B2B Marketing with Kacie Jenkins, Head of Marketing for Claude Code at Anthropic - Ep 76
MAR 31, 2026
Building a Movement Through B2B Marketing with Kacie Jenkins, Head of Marketing for Claude Code at Anthropic - Ep 76
Kacie Jenkins is the Head of Marketing for Claude Code at Anthropic. Prior to joining Anthropic, Kacie led marketing at Sendoso as SVP of Marketing, Sourcegraph as VP of Marketing, and Fastly as VP of Marketing, to name a few.Kacie joins co-hosts Craig Rosenberg and Matt Amundson to unpack what B2B brands need to learn from B2C companies in order to build bold, unforgettable brands that increase revenue and redefine markets. Plus, Kacie outlines why B2B startups need to see building a founder brand as a pipeline engine, how to move beyond broken marketing attribution systems, and why brand marketing is making a massive comeback.Also, Kacie shares the outcome of all her speakers getting food poisoning before an event, Craig explains why he’s bringing his son to Vegas, and Matt states his stance on the existence of ghosts. Critical TakeawaysFounder-led brand and content works because buyers want conviction from the people shaping the company, not just polished messaging from the brand account. The key to building a strong founder brand is finding the intersection of three things: 1. What is the founder an expert at? 2. What makes the founder utterly unique? 3. What does the target audience want and need?A bold brand doesn't mean punching competitors; it means being so weird, human, and mission-driven that people can't stop thinking about you. At Fastly, this meant leaning into engineer culture with quirky campaigns (literal messenger pigeons), bright red branding mirroring the founder's personality, and taking public stands on internet ethics. Find what makes your company authentically different and lean all the way into it.Your founder is the person with the most conviction on your team, and that conviction is what cuts through noise in crowded categories. Marketing should treat building and amplifying the founder's narrative as a top priority, not a side project. Invest time sitting with the founder to uncover what they stand for, what they hate, and what future they're building — then help them show up consistently.Sales leaders should map executive posts, thought leadership clips, and campaign creative to relevant strategic accounts, then use that content to multi-thread and re-engage deals. When a founder or visible executive has market credibility, reps get warmer entry points and stronger follow-up moments.Values only count when customers can feel them. If the brand story stops at messaging, buyers will eventually spot the gap. For example, Fastly’s brand worked because their stance showed up in customer selection, customer success, and even how they defined who they wanted to win with in the market.Chapters00:00 - Episode Preview00:51 - Spooky Baseball02:20 - Introducing Kacie Jenkins, Head of Marketing for Claude Code at Anthropic05:46 -  Accidentally Hosting a Spooky Customer Advisory Board Retreat12:53 - What Happens When All Your event Speakers get Food Poisoning19:03 -  How Founders Can Seize the Story of Their Category and Own The Narrative35:48 - How to Build Bold Brands for B2B SaaS41:22 - Why brand fails without founder buy-in47:23 - Marketing Attribution is Broken. Now what?Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“The key to winning is real, true, authentic differentiation.” - Kacie JenkinsConnect with KacieLinkedIn: https://www.linkedin.com/in/kaciejenkins/ Anthropic Website: https://www.anthropic.com/ Claude Code Website: https://claude.com/product/claude-code ShoutoutsRuby James: https://www.linkedin.com/in/rubyjameslinkedin/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Artur Bergman: https://www.linkedin.com/in/crucially/  Katie Penner: https://www.linkedin.com/in/kathrynpenner/ Kris Rudeegraap: https://www.linkedin.com/in/rudeegraap/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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58 MIN