The Transaction

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.

  1. Building a Movement Through B2B Marketing with Kacie Jenkins, Head of Marketing for Claude Code at Anthropic - Ep 76

    7 HR AGO

    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 Takeaways Founder-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. Chapters 00:00 - Episode Preview 00:51 - Spooky Baseball 02:20 - Introducing Kacie Jenkins, Head of Marketing for Claude Code at Anthropic 05:46 -  Accidentally Hosting a Spooky Customer Advisory Board Retreat 12:53 - What Happens When All Your event Speakers get Food Poisoning 19:03 -  How Founders Can Seize the Story of Their Category and Own The Narrative 35:48 - How to Build Bold Brands for B2B SaaS 41:22 - Why brand fails without founder buy-in 47:23 - 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 Jenkins Connect with Kacie LinkedIn: https://www.linkedin.com/in/kaciejenkins/ Anthropic Website: https://www.anthropic.com/ Claude Code Website: https://claude.com/product/claude-code Shoutouts Ruby 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!

    58 min
  2. How Courageous Marketing Leadership Builds Bold Brands with Udi Ledergor, Chief Evangelist at Gong - Ep 75

    17 MAR

    How Courageous Marketing Leadership Builds Bold Brands with Udi Ledergor, Chief Evangelist at Gong - Ep 75

    Udi Ledergor is the Chief Evangelist at Gong and is firmly amongst the upper echelon of the, as yet to be founded, B2B marketing leader hall of fame, having led outstanding teams as both a Vice President of Marketing and Chief Marketing Officer at five B2B SaaS companies for over two decades. Alongside steadfast co-hosts Craig Rosenberg and Matt Amundson, Udi shares how he has crafted one of the top SaaS brands without losing its exceedingly human touch, how Gong thinks about the content they create as part of their marketing strategy, and to use AI to raise your bar for creative thinking by filtering out the obvious crap. Plus, Udi unpacks the three critical marketing leadership lessons he learned the hard way when a mistake in an email marketing campaign almost spiraled into a massive issue for one of the premier B2B SaaS brands in Silicon Valley today.    Also, Craig admits to claims he confused someone on a call, Matt waxes poetic about a B2B SaaS company he doesn’t work for, and Producer Sam revels in an ever-elusive mention of the show notes.  Critical Takeaways When a marketing mistake goes public, marketing leaders need to act decisively within hours, not days, and own it personally. A swift action paired with a personal response can de-escalate most complicated situations and help to quell even irate customers. By quickly taking personal accountability for the issue, you can turn a brand crisis into a trust-building moment.Teams should treat complaints as a signal, not the sample size. If a dozen people took the time to complain, many more probably felt the same way and stayed quiet. That is a strong operating principle for brand, product, and customer comms teams: they should respond to the unseen audience, not just the visible inbox.A key to building Gong’s human-feeling brand was deliberately connecting "trusted thought leader" with "relaxed, friendly person who wants to help you out" during an early brand workshop. Most B2B brands default to authoritative-plus-stuffy; product marketers and brand teams should explicitly codify an approachable, human counterweight in their brand guidelines.Use AI suggestions to find and filter out the obvious crap that everyone else would do in their marketing strategy. LLMs are a synthesis of (pretty much) everything on the internet, which means they’re great at telling you about what’s already out there. The next time you’re coming up with ideas for a marketing campaign, ask your LLM of choice for its recommendations and use those as a guide for what not to do.Rather than going fully with either gated or ungated content, using them in tandem can increase visibility and conversions. When sharing ungated content publicly, link to relevant gated assets and resources from within the ungated piece of content. This way, you get the visibility benefits of ungated content while getting your gated assets in front of a larger target audience. Chapters 00:00 - Episode Preview 00:56 - Craig Flounders While Filibustering to Find an Excuse For His Profile Photo Fiasco 03:16 - Introducing Udi Ledergor, Chief Evangelist at Gong 05:46 - 3 Critical Marketing Lessons Learned from an Email Campaign that Almost Ruined a Massive B2B SaaS Brand 17:02 - How Gong Intentionally Built an Authentic, Sincere, & Human Brand for A B2B SaaS Startup 22:06 - Reimagining B2B Marketing Events To Optimize for Guest Experience 28:48 - Using AI as a Quality Filter for Marketing Ideas 33:36 - The Two Ways to Use AI in Your Work 35:19 - Where Gong Lands in the Gated-versus-Ungated Content Debate 45:26 - The Basics of Email Marketing That Still Work in B2B 47:45 - The Bait & Switch Twitter Play for Boosting Web Traffic For Startups 51:31 - How Gong Develops its Content Marketing and Distribution Strategy Together Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/ Epic Quotes “We're sometimes over-reliant on all this automation crap. We like that it saves our team work, but we don't realize what we're giving up in return.” - Udi Ledergor“The worst thing that can happen to you is not that some people hate what you're doing. The worst thing that can happen to you is indifference.” -  Udi Ledergor Connect with Udi LinkedIn: https://www.linkedin.com/in/udiledergor/ Gong’s Website: https://www.gong.io/ Udi’s Book: https://a.co/d/0Cix9Ll Udi’s Website: https://www.udiledergor.com/  Shoutouts Ruby James: https://www.linkedin.com/in/rubyjameslinkedin/ Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’ Episode: https://open.substack.com/pub/thetransaction/p/solving-the-go-to-market-skills-crisisMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-inBrent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: https://open.substack.com/pub/thetransaction/p/rebuilding-b2b-customers-confidenceKyle Lacy: https://www.linkedin.com/in/kylelacy/ Top Swear Words - Gong: https://www.gong.io/blog/how-cursing-impacts-sales Alec Paul: https://www.linkedin.com/in/alecjpaul/ Alec’s Episode: https://open.substack.com/pub/thetransaction/p/becoming-a-linkedin-master-with-alec Danny Hutto: https://www.linkedin.com/in/dannyhutto/  Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

    59 min
  3. Positioning Needs to Underpin Every Part of Your Brand Strategy with Stacey Epstein, CEO of Structured - Ep 74

    26 FEB

    Positioning Needs to Underpin Every Part of Your Brand Strategy with Stacey Epstein, CEO of Structured - Ep 74

    We’ve got the perfect guest to help you understand how your brand can stand out and provide a uniquely incredible experience for customers in the AI era. Stacey Epstein is the CEO of Structured, the only AI-native channel marketing platform purpose-built for complex partner ecosystems. She is also the Host of AI’ve Got Questions, a casual, candid podcast for marketers trying to make sense of the fast-moving world of AI. Stacey joins co-hosts Matt Amundson and Craig Rosenberg to discuss why your positioning framework needs to be at the core of every marketing campaign, how hiring for taste drives differentiation, and how to inject the voice of your customers into your brand. Plus, Stacey shares how to maximize the impact of your CEO or Founder throughout your marketing. Also, Craig talks about the miracle of birth, Matt mixes up the abbreviations of an African country, and Producer Sam expounds on the etymology of the word “czar”.  Critical Takeaways Before you start executing any marketing tactics, you need to develop a strong positioning framework that clearly articulates what your company does, why it matters, who the buyer is, and what makes you different. Way too many B2B companies are still doing "random acts of marketing" where every campaign differs from the website messaging, creating inconsistent brand experiences that confuse buyers and dilute impact.As AI handles more aspects of content creation, campaign distribution, and administrative tasks, marketing teams should prioritize hiring "tastemakers" who demonstrate exceptional judgment in evaluating strategic creative decisions. The ability to curate, refine, and elevate work, whether human-made or AI-generated, matters more than the ability to execute tactical tasks manually.Treat your S-1 as the foundation for all Go-To-Market activities. It should be the basis of your positioning, informing everything from why you exist, what your product does, points of competitive differentiation, and your future visionOrganizations need a centralized AI leader, whether in marketing ops, revenue ops, or IT, to coordinate AI initiatives across functions and prevent teams from burying themselves in disjointed AI projects. This role ensures strategic alignment, prevents redundant tool purchases, and helps teams focus AI adoption on high-impact use cases rather than experimenting randomly. Chapters 00:00 - Episode Preview 00:42 - Craig’s Story of Endings and New Beginnings 02:46 - Introducing Stacey Epstein, CEO of Structured 07:16 - Accidentally Sending an Embarrassing Email to Every Co-worker in an Entire Region 15:34 - Why Positioning is Foundational to Your Brand and Storytelling 21:29 -  How to Get Better Input on Marketing from Founders & CEOs 31:58 - What Stacey's Learned about AI From Hosting her Podcast 34:54 - Why You Need to Hire “Taste Makers” in an AI-first world 41:50 - A Brief Aside on the Etymology of Czar/Tsar 43:35 - Why Companies are Hiring GTM Engineers & The Impact They're Having 45:58 - How to Lead AI Implementation in Your Company Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/ Epic Quotes “ Who owns AI in the company?” - Stacey Epstein“ I love coming back to use cases, because use cases come back to the benefit for the company. So instead of telling me what the product does, tell me how that would be used.” - Stacey Epstein Connect with Stacey LinkedIn: https://www.linkedin.com/in/staceyepstein/ Magnetic GTM Website: https://www.magneticgtm.com/ Podcast: https://aivegotquestions.buzzsprout.com/ Structured Website: https://structured.ai/  Shoutouts David Boskovic: https://www.linkedin.com/in/dboskovic/ David’s Episode: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-marketLisa Cole: https://www.linkedin.com/in/lisacole01/

    55 min
  4. The AI-Enabled Future of Sales with James Kaikis, Founder of GTMshift - Ep 73

    9 FEB

    The AI-Enabled Future of Sales with James Kaikis, Founder of GTMshift - Ep 73

    The landscape of go-to-market in the B2B SaaS world is shifting rapidly, but thankfully we’ve got just the person to help you get ahead and innovate. James Kaikis is the Founder of GTMshift, Co-Founder of SolutionExec, Co-Founder of AI Sales Studio, and Host of The GTMshift Interview Series. James joins Matt Amundson and Craig Rosenberg to unpack the evolving role of sales reps, how to use the GTM Innovator’s Framework to stay up on AI advances, and why B2B SaaS companies must refocus their GTM motions on their customers. Plus, James shares his top spots to eat in Chicago. Also, Craig calls Matt a technical buyer, Matt rates Craig’s follicular health, and Producer Sam forgets how math works.  Critical Takeaways Technical buyers have done extensive research before ever talking to you and know their problems better than you do. Stop running rigid qualification frameworks like BANT or MEDDIC that waste their time asking questions they've already answered internally. Instead, get straight to demonstrating how your solution solves their specific problem with their actual data, positioning yourself as a consultant helping them buy rather than a salesperson trying to extract information.Sales reps must be able to demonstrate the product themselves for lower-complexity solutions, especially when selling to other sales or marketing professionals. If you're selling sales technology but can't give a demo because "that's what SEs do," you've already lost credibility with your buyer. Invest time learning your product deeply enough to have hands-on conversations, or accept that AI-proficient competitors will replace you.Shift your focus from new logos to customer expansion. B2B SaaS companies are now generating more net new revenue from existing customers than new logo acquisition for the first time. Every customer you close should have a clear expansion roadmap within the first 90 days, with multiple upsell opportunities identified before implementation completes.Vertical SaaS represents one of the few remaining competitive moats as horizontal solutions get commoditized overnight by AI. Sales reps must develop deep expertise in specific industries—understanding regulatory requirements, workflow nuances, and sector-specific language that generic reps cannot replicate. For example, if you're selling into pharmaceutical, financial services, or manufacturing, you need to speak their language authentically or technical buyers will immediately dismiss you as lacking credibility.The traditional AE role that handled prospecting, discovery, demoing, forecasting, product knowledge, and closing is fundamentally broken because it asks too much of one person. Your role must narrow to being a customer-centric problem solver who builds trust and delivers value, while AI handles pipeline generation and SEs handle technical depth. Sales professionals who cannot adapt to this narrower, more specialized role will be replaced by solutions engineers who understand the product deeply and can build trust through hands-on demonstrations rather than sales techniques.Chapters00:00 - Episode Preview00:50 - Checking in on Craig’s Follicular Growth, Grooming & Glasses03:12 - Introducing James Kaikis, Founder of GTMshift09:06 - The Life-changing Impact AI Innovation Had on James23:17 - B2B SaaS has Forgotten about the Customer & Their Experience31:18 -  The Changing Role of Sales Reps & Why Your Next Account Exec Should be a Solutions Engineer41:02 - How the Next Generation of Sales Reps will be Trained & Interact with AI50:11 - The Opportunity for Experiential Selling that AI Makes Feasible59:04 - Quick Review of the Chicago Cuisine Scene Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/ Epic Quotes “We have lost sight in B2B SaaS of who matters.” - James Kaikis“Trust and value are the ultimate currency and this next wave of B2B SaaS.” - James KaikisConnect with James LinkedIn: https://www.linkedin.com/in/jameskaikis/ GTMShift Website: https://gtmshift.com/ AI Sales Studio Website: SolutionExec Website: https://solutionexec.com/ The GTM Shift Interview Series: https://gtmshift.com/the-gtmshift Linktree: https://linktr.ee/jkaikis Shoutouts Doug Landis: https://www.linkedin.com/in/douglandis/ Doug’s Episode: https://open.substack.com/pub/thetransaction/p/overcoming-outbound-challenges-with Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ David Boskovic: https://www.linkedin.com/in/dboskovic/ David’s Episode: https://thetransaction.substack.com/p/building-an-ai-first-go-to-market MIT Study on AI Adoption: https://mitsloan.mit.edu/ideas-made-to-matter/productivity-paradox-ai-adoption-manufacturing-firms Craig’s Episode on GTM Shift: https://gtmshift.com/the-gtmshift/everything-s-back-on-the-table-why-ai-is-revolutionizing-gtm-with-craig-rosenberg Jeff Margolese’s Episode on GTM Shift: https://gtmshift.com/the-gtmshift/the-solution-exec-guide-to-navigating-the-great-ai-shift-with-jeff-margolese Dave Brock: https://www.linkedin.com/in/davebrock/ Dave’s Episode: https://open.substack.com/pub/thetransaction/p/really-knowing-your-customer-with?utm_campaign=post-expanded-share&utm_medium=web Trivoli Tavern: https://www.trivolitavern.com/trivoli Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

    1hr 3min
  5. How the Most Successful B2B Marketing Teams are Winning with Omar Akhtar, Founder of Benchmarker - Ep 72

    20 JAN

    How the Most Successful B2B Marketing Teams are Winning with Omar Akhtar, Founder of Benchmarker - Ep 72

    Surprise: Doing ‘more with less’, doesn’t actually work in B2B marketing, and today’s guest has the data to show it. Omar Akhtar is the Founder and Principal Analyst of Benchmarker and the Director of Content at UserTesting. Omar joins co-hosts Matt Amundson & Craig Rosenberg to dive into the B2B marketing data from Benchmarker’s latest survey, why the most successful companies are spending more on brand than demand, and how events have emerged as one of the top growth channels in go-to-market. Plus, Omar digs into when to prioritize paid versus organic channels in your marketing mix. Also, Craig outlines the plans for his kid’s booze-fueled birthday party, Matt laughs at an inopportune moment, and Producer Sam says ‘raccoon’.  Critical Takeaways Doing more with less is dead. You can’t cut your way to growth. Marketing leaders need to choose between efficient growth or exponential growth and spend accordingly. The companies that are actually hitting or exceeding their targets are spending at least the same, if not more, on brand as they are on demand. The companies that are performing the worst are overspending on demand over brand marketing.When new account growth is the priority, marketing teams should lean into paid search and paid social even though they’re expensive, because these paid channels can deliver faster growth and can outperform organic channels for reach.Dinners and small events can be great, but you can easily ruin them by being overly pushy and sales-y. If someone is talking product before anyone’s had a drink, you need to nip that in the bud. Also, some consultants can be pitchy, so invite them selectively.SaaS marketers are great at deploying amazing new tactics; however, on the whole, they lack a strong foundation in the marketing basics. Before you learn about the next bleeding-edge tool, take a minute to brush up on the building blocks, like positioning, targeting, and messaging. Chapters 00:00 - Episode Preview 01:23 - Introducing Omar Akhtar, The Founder of Benchmarker 03:54 - A Perilously Precipitous Sales Call 06:01 - How Omar Moved From Rockstar to B2B Marketing Analyst 12:26 - Craig’s Dog Crashes the Party in Multiple Ways 13:32 - What Benchmarker’s Data has Revealed about Successful B2B Marketing Teams 21:26 - Why the Best Marketing Teams are Spending More on Brand Marketing 23:56 - Where Content Marketing Fits in the Modern B2B Marketing Mix 30:34 - Events & Small Dinners are Converting Like Crazy, but Please Don’t Overdo Them 37:24 - No Amount of Great Marketing Can Overcome a Crap Product, Have a Good Product & Execute the Basics of Marketing Well 44:11 - What Makes Clay’s Marketing So Special 50:21 - How Gong Survived the Latest SalesTech Revolution & is Now Thriving Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/ Epic Quotes “ This idea that we used to have for a long time, where you have to do more with less doesn't hold true anymore, because you can't cut your way to growth anymore.” - Omar Akhtar“We’re really in a B2B SaaS recession.” - Omar Akhtar Connect with Omar LinkedIn: https://www.linkedin.com/in/omarbilalakhtar/ Benchmarker Website: https://www.benchmarkerdata.com/ UserTesting Website: https://www.usertesting.com/  Shoutouts Amy Holtzman: https://www.linkedin.com/in/aholtzman/ Amy’s Episode: https://open.substack.com/pub/thetransaction/p/crafting-an-exceptional-event-marketing?r=3iae7z&utm_campaign=post&utm_medium=web Udi Ledergor: https://www.linkedin.com/in/udiledergor/ Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’s Episode:  https://open.substack.com/pub/thetransaction/p/solving-the-go-to-market-skills-crisis?utm_campaign=post-expanded-share&utm_medium=web Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in?utm_campaign=post-expanded-share&utm_medium=web  Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

    56 min
  6. “The Who is Everything” with Kathy Macchi, Co-Founder of Inverta - Ep 71

    8 JAN

    “The Who is Everything” with Kathy Macchi, Co-Founder of Inverta - Ep 71

    For our first episode of the new year, we’re thrilled to welcome special guest Kathy Macchi,  the Executive Vice President, Innovation & Co-Founder at Inverta. Kathy joins co-hosts Craig Rosenberg & Matt Amundson to discuss where so many go-to-market leaders go wrong with their segmentation, why your message matters more than the channel you deliver it through, and how to design a successful mid-market marketing org amidst massive pressure for budget cuts. Also, Craig bemoans eating vegetables, Matt gives an update on Craig’s health, and some may have been kidnapped at Producer Sam’s house.  Critical Takeaways Before chasing hyper-specifc and fancy AI tools, codify ICP, targeting, messaging, and what “good” outreach looks like. Then use AI to scale research and execution (with humans judging output), instead of hoping automation will invent strategy from scratch.If the account list is wrong, everything downstream gets harder (sales cycle, conversion, retention, even CSM load). Institutionalize segmentation by use case and continuously prune/refresh the target universe instead of debating tactics in the abstract.Stop obsessing over which channels you’re using and start focusing more on whether you have something worth saying to a specific buyer group. Then should ship that personalized, relevant message across every relevant channel as an integrated system, not as disconnected one-off campaigns. Chapters 00:00 Harrowing Health Foods, Rave Recaps, & Tennis Talk08:30 Introducing Kathy Macchi, Co-founder at Inverta 12:40 The Business Concerns Coming up In CMO Councils, Primarily AI & Budget Cuts 18:43 Why Cultivating Good Taste Transcends AI Advancements & Solving The Problem Before Adding AI Tools 30:27 AI's Impact on B2B Marketing Jobs and Economy 32:37 Rethinking Marketing and Business Processes with AI 34:06 The Role of Effective Targeting for Account-Based Marketing in the AI-era 37:02 Effective Use of AI in Marketing 42:13 Messaging + B2B Marketing Channel Strategies and Multi-Channel Marketing 53:04 B2B Sales and Territory Planning Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/ Epic Quotes “The who is everything” - Kathy Macchi“ We forgot that early pipeline, until you figure it out, costs money.  It costs money and you're going to fail.” - Craig Rosenberg Connect with Kathy LinkedIn: https://www.linkedin.com/in/kathy-macchi-aa148b/ Inverta Website: https://www.inverta.com/  Shoutouts Geoffrey Moore: https://www.linkedin.com/in/geoffreyamoore/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Carlos AlcarazDavid Boskovic: https://www.linkedin.com/in/dboskovic/ Our Episode with David: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-marketOmar Akhtar: https://www.linkedin.com/in/omarbilalakhtar/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

    1hr 4min
  7. Escaping B2B SaaS Dashboard Hell with Ray Rike & Dave Kellogg - Ep 70

    08/12/2025

    Escaping B2B SaaS Dashboard Hell with Ray Rike & Dave Kellogg - Ep 70

    If you feel like your pipeline is broken, your CAC is bloated, and your dashboards are lying to you… you’re FAR from the only one.  Joining the show are the Metrics Brothers, Ray Rike and Dave Kellogg! Ray is the Founder & Chief Evangelism Officer of Benchmarkit, Host of Metrics That Measure Up, a Founding Member of the SaaS Metrics Standards Board, and is an LP at Stage 2 Capital. Dave co-hosts The Metrics Brothers Podcast, writes the incomparable ‘Kellblog’, and is an EIR at Balderton Capital. Dave and Ray join co-hosts Matt Amundson and Craig Rosenberg to discuss the importance of brand investment in the AI age, overcoming the pipeline generation crisis in B2B SaaS, and how GTM leaders can drain the “metrics swamp.” Plus, Dave divulges which SaaS metrics he finds loathsome and Ray shares his unique method for calculating Marketing CAC. Also, Craig airs an ambrosia-related grievance, Matt unveils an old school tactic he’s still using, and Producer Sam falsely announces an exclusive scoop on The Transaction.  Critical Takeaways Treat answer engine optimization (AEO) as a real channel, not a buzzword. As answer engines and generative AI search tools aggregate from dozens of sources but surface only a few. Meaning that you either show up in the top 2-3 responses or you effectively disappear. Teams should build use-case-level content, distribute it widely, and make it novel enough that answer engines want to quote it, while also building their own audience (newsletter, podcast, communities) so they’re not fully dependent on Google’s (or ChatGPT’s) algorithm.Inbound hand-raisers are a much better primary brand KPI than ‘share of voice’ measurements. Watch what percent of qualified pipeline and new ARR comes from inbound hand-raisers. GTM leaders should explicitly target a higher share of pipeline from inbound, track its close rates and ACVs versus outbound, and use that to justify continued brand and content investment.Focus more on the number of opportunities and cost per opportunity, not just total pipe. Revenue teams should watch both volume and dollars by source, so they can see, for example, whether brand-driven inbound is generating fewer but much better-quality opportunities and adjust their mix and SLAs accordingly.If you want overall efficiency, use Marketing CAC (sales + marketing over new ARR); if you want to compare programs, use pipeline generated divided by demand-gen program spend only. GTM leaders should keep CAC reserved for the full go-to-market machine, then use pipe-to-spend for campaign and channel decisions, excluding fixed headcount so they understand the ROI of the next incremental dollar.Sales and marketing leaders must acknowledge the current “pipeline crisis” in B2B SaaS, characterized by insufficient pipeline coverage and declining efficiency. Teams should track both the volume and cost of pipeline generated, and forecast pipeline coverage across all sources (marketing, SDRs, alliances, PLG, etc.) early and often.Aligning on metrics is a long-term, iterative process that requires persistence and cross-functional buy-in.  Chapters 00:00 Episode Preview 01:48 Introducing Ray Rike and Dave Kellogg, The Metrics Brothers 05:40 How GTM Leaders can Escape from their ‘Dashboard Hell’ 11:08 Which Metrics Matter to Your Board 18:37 Overcoming The B2B SaaS Pipeline Crisis 24:38 The Difference Between Search Engine Optimization & Answer Engine Optimization 29:52 Why Brand Still Matters in the age of AI & How to Measure Brand 45:21 Why B2B Marketers Need to Measure both Opportunity Count & Cost Per Opportunity 47:38 Why Pipeline Coverage Ratio is so Critical for B2B SaaS Startups 51:21 Examining Tantalus & The Cultural Impact of Ambrosia in All of Its Forms Join our Newsletter to get bonus content & never miss an episode: https://thetransaction.substack.com/ Epic Quotes “The faster growing companies actually are spending more on brand than on demand.” - Ray Rike“ My least favorite SaaS metric? Rolling four-quarter pipeline.” - Dave Kellogg“ Branding is marketing without a call to action.” - Dave Kellogg Connect with Ray & Dave Ray’s LinkedIn: https://www.linkedin.com/in/rayrike/ Dave’s LinkedIn: https://www.linkedin.com/in/kelloggdave/ The Metrics Brother Podcast: https://podcasts.apple.com/us/podcast/the-metrics-brothers-fka-saas-talk/id1687214133 Metrics that Measure Up Podcast: https://podcasts.apple.com/us/podcast/metrics-that-measure-up/id1525571613 Benchmarkit Website: https://www.benchmarkit.ai/ Dave’s Blog: https://kellblog.com/ Balderton Capital: https://www.balderton.com/  Shoutouts Ray’s first Episode on The Transaction: https://open.substack.com/pub/thetransaction/p/harnessing-the-magic-of-metrics-with Avinash Kaushik: https://www.linkedin.com/in/akaushik/ Avinash’s Newsletter: https://www.kaushik.net/avinash/marketing-analytics-intersect-newsletter/ Avinash’s SEO vs AEO article: https://www.kaushik.net/avinash/ai-age-marketing-bye-seo-hello-aeo/ Omar Akhtar: https://www.linkedin.com/in/omarbilalakhtar/ Benchmarker: https://www.benchmarkerdata.com/ Exit Five: https://www.exitfive.com/ Our Episode with Dave Gerhardt: https://open.substack.com/pub/thetransaction/p/ai-idea-starters-influencers-and Carilu Dietrich: https://www.linkedin.com/in/cariludietrich/ Our Episode with Carilu: https://open.substack.com/pub/thetransaction/p/advisor-avengers-assembling-your Jon Miller: https://www.linkedin.com/in/jonmiller2/ Our Episode with Jon: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in Udi Ledergor: https://www.linkedin.com/in/udiledergor/ Bill Macaitis:

    56 min
  8. Account Management is Your Startup’s Growth Department with Alex Raymond, Founder of AMplify - Ep 69

    18/11/2025

    Account Management is Your Startup’s Growth Department with Alex Raymond, Founder of AMplify - Ep 69

    With so much attention within the go-to-market world paid to marketing and sales, account management, which is arguably just as important, rarely gets its due. Alex Raymond is the Founder of AMplify and Host of the Account Management Secrets podcast. Alex joins co-hosts Matt Amundson and Craig Rosenberg for the first major discussion on the podcast of account management and its crucial role in growing revenue and overall company value for SaaS vendors.  Plus, Alex breaks down how CROs should organize their team, what types of people make for the best account managers, and why in-depth stakeholder mapping of customer accounts is so critical to growing revenue.  Also, Craig mixes up country singers, Matt discovers a great path, and Producer Sam compares someone’s comment to military ordinance.  Critical Takeaways Account management should be positioned as the "growth department" of your company, responsible for driving profitable revenue from existing customers. Shift the mindset from reactive support to proactive growth, ensuring account managers are empowered and resourced to expand accounts, not just retain them.Start building account management capabilities early, even before you hit $10M in revenue, so you can learn from customers, reduce churn, and set the foundation for compounding growth. Don’t wait until churn or customer growth becomes a problem you’re hearing about in your board meetings.Ambiguity about who owns customer growth leads to missed opportunities. Great account managers are creative problem solvers with strong business sense, often with consulting backgrounds. They should be able to see the big picture, ask insightful questions, and build long-term relationships, rather than just focusing on renewals or incremental expansions. PS: former consultants make for great AMs.Build Robust Stakeholder Maps and Engage at Multiple Levels.Vendors need to actually do QBRs (Quarterly Business Reviews). Go talk to your darn customers.Chapters 00:00 - Episode Preview 01:00 - Trouble with Tickets 03:44 - Introducing Alex Raymond, Founder of AMplify 05:59 - The Role of Account Management in The Growth of B2B Startups 12:27 - The Power of Exponential Thinking for Entrepreneurs 16:01 - A Quick Sidebar about Business Events and Dining in Boulder 19:31 - Why Account Management is a Revenue Function & When Your Startup Needs Account Managers 29:15 - Where Account Management Should Fit in Your Revenue Team’s Organizational Design  36:26 - What To Look for When Hiring Great Account Managers 42:03 - When Account Managers Should Be Brought into New Deals 49:13 - Developing Complex Stakeholder Maps for Customer Accounts Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/ Epic Quotes “ The CRO should be managing the entirety of their revenue cycle, not just some slice of it.” - Alex Raymond“ Land and expand has never been more important than it is right now.” - Alex Raymond“ I just never, ever want to be a CEO.” - Matt Amundson Connect with Alex LinkedIn: https://www.linkedin.com/in/afraymond/ Website: https://www.amplifyam.com/ Podcast: https://www.amplifyam.com/podcast  Shoutouts Craig’s Episode on Alex’s Podcast: https://www.amplifyam.com/account-management-secrets/why-post-sale-is-still-broken-and-what-to-do-about-it-craig-rosenberg Mike Rapp: https://www.linkedin.com/in/michaelrapp-intelepeer/ Alex’s Episode with Mike Rapp: https://www.amplifyam.com/account-management-secrets/serve-retain-sell-how-account-management-builds-revenue-leaders-mike-rapp  Dr. Benjamin Hardy: https://www.linkedin.com/in/drbenjaminhardy/  Conscious Entrepreneur Summit: https://consciousentrepreneur.us/ The Science of Scaling by Dr. Benjamin Hardy & Blake Erickson: https://a.co/d/eTUlHeV 10x is Easier Than 2x by Dan Sullivan & Dr. Benjamin Hardy: https://a.co/d/1kf8tSe  Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

    59 min
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About

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.

Information

  • Creator
    Craig Rosenberg & Matt Amundson | B2B Sales & Marketing Experts - Hosts of The Transaction
  • Years Active
    2024 - 2026
  • Episodes
    80
  • Rating
    Explicit
  • Copyright
    © The Transaction
  • Show Website
    The Transaction

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