The Transaction

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!

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-crisis
• Maria 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-in
• Brent Adamson: https://www.linkedin.com/in/brentadamson/ 
• Brent’s Episode: https://open.substack.com/pub/thetransaction/p/rebuilding-b2b-customers-confidence
• Kyle 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!

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 vision
• Organizations 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-market
• Lisa Cole: https://www.linkedin.com/in/lisacole01/ 

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.

Chapters
00:00 - Episode Preview
00:50 - Checking in on Craig’s Follicular Growth, Grooming & Glasses
03:12 - Introducing James Kaikis, Founder of GTMshift
09:06 - The Life-changing Impact AI Innovation Had on James
23:17 - B2B SaaS has Forgotten about the Customer & Their Experience
31:18 -  The Changing Role of Sales Reps & Why Your Next Account Exec Should be a Solutions Engineer
41:02 - How the Next Generation of Sales Reps will be Trained & Interact with AI
50:11 - The Opportunity for Experiential Selling that AI Makes Feasible
59:04 - 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 Kaikis

Connect 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!

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!

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 Talk
08:30 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 Alcaraz
• David Boskovic: https://www.linkedin.com/in/dboskovic/ 
• Our Episode with David: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-market
• Omar Akhtar: https://www.linkedin.com/in/omarbilalakhtar/

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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:

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!

The immense hype around AI agents is positively palpable, but is there value in adopting an army of AI minions today or is the promise of agentic AI still fictitious pulp?

Here to help illuminate and elucidate the role of AI agents is Gabe Larsen, the Chief Revenue Officer at Signals and the former Chief Marketing Officer of Kustomer. 

Gabe joins co-hosts Matt Amundson and Craig Rosenberg for a deep dive into how agentic AI coupled with signal-based marketing succeeds in go to market where Account-Based Marketing failed in its execution. We get into whether startups should build or buy the tools they need, which new metrics your board might be looking for, and what customers really want to hear about from vendors.

Plus, Gabe bids goodbye to the age of software tools while welcoming in the AI-powered teammate economy.

Also, Craig vehemently denies accusations of scowling, Matt shares his preferences on the intricacies of the English language, and Producer Sam asks a dumb question.

Critical Takeaways

• Agentic AI tools need to provide omni-channel execution in order to offer real value and impact to sales and marketing teams. 
• The combination of Signals + Agents outperforms Account-Based Marketing in the way it has been traditionally deployed. However, the core ideas of ABM, such as Ideal Customer Profiles, Target Accounts, Personalization, etc., still hold true. In fact, the advances in AI-powered martech have now made the original promise and vision of ABM possible.
• In the build vs buy debate, much of what has been built and is being built in-house is far too brittle to accommodate the regular use of a revenue team. You don’t want your whole custom-built workflow to break every time someone makes a minor change to something as small as an email subject line. However, the solutions that are going to succeed and ultimately be bought must be capable of handling the custom needs and workflows of the users. If the available tools are too rigid for customers, then they will look to build their own workarounds, solutions, and eventually, replacement tools.
• As the “customization economy” takes hold, go-to-market teams should seek vendors that offer flexible, customizable solutions rather than rigid, templatized products. From the vendor side, take note that buyers are gravitating toward platforms that allow them to tailor workflows to their unique needs, and if you fail to provide this flexibility, you will be left behind.
• Customers crave real guidance from vendors, not just hype about the new features you added. The most successful vendors will be those who offer clear, prescriptive playbooks and best practices (Think HubSpot or Marketo).

Chapters

00:00 - Episode Preview

02:16 - Introducing Gabe Larsen, the Chief Revenue Officer of Signals

04:53 - Learning The Costly Difference between Michael and Michelle 

09:23 - Catastrophic Sales Kickoff Stories

14:26 - The Dim Sum Disaster

17:29 - Why Signals-based Marketing + AI Agents are outperforming Traditional Account-Based Marketing

26:15 - Builders versus Buyers & Why Tools are Out and Teammates are In

31:56 - The Role of AI in Modern B2B Marketing

45:01 - The Future of AI-Powered Workforces

48:14 - An AI Vendor's Perspective on Pricing for AI Tools & AI Agents

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “The market’s separating into builders and buyers and I think we’re establishing more buyers.” - Gabe Larsen
• “ Tools are gone, teammates are in.” - Gabe Larsen 
• “This is the customization economy” - Craig Rosenberg

Connect with Gabe

• LinkedIn: https://www.linkedin.com/in/gabelarsen/ 
• Signals Website: https://getsignals.ai/ 

Shoutouts

• David Boskovic: https://www.linkedin.com/in/dboskovic/ 
• David’s Boskovic’s episode: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-market

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

The vast majority of companies that think they are running ABM (Account-Based Marketing) are not actually running ABM. Not only that, they wouldn’t recognize a real ABM strategy if one came up and slapped them in the face with a stack of direct mailers.

Davis Potter is the CEO & Co-Founder of ForgeX, a research and advisory firm that helps B2B companies modernize their Account-Based Go To Market and AI strategies. Davis joins co-hosts Matt Amundson and Craig Rosenberg for an exploration of the current state of ABM (Account-Based Marketing), what it takes to drive impact of using AI in GTM Execution, and how to right-size the B2B marketing tactics to each account. 

Also, Craig uses a ‘Matt-ism’, Matt distinguishes cuddling from canoodling, and Producer Sam fixes a problem with his face. 

Critical Takeaways

• There are three core account-based marketing models: Enterprise ABM (1:1 and 1:few), Growth ABM (1:many at scale), and Deal Acceleration (targeted support for individual opps).
• Shift from short, one-off marketing campaigns to holistic, always-on programs that run continuously throughout the year. Build a playbook of ABM tactics (e.g., webinars, executive dinners, personalized landing pages, LinkedIn ads) and deploy them based on account tier and industry segment. This enables ongoing engagement and better adapts to complex B2B buying cycles.
• Select and tier accounts based on informed revenue potential, not just logo desirability or gut feel. Analyze first, second, and third-party signals, as well as customer LTV and microsegments, to prioritize accounts for deeper personalization and resource allocation. For example, reserve direct mail and executive engagement for tier one, while using scalable digital tactics for lower tiers.
• Unify your target account lists across sales, marketing, and customer success to drive alignment and efficiency. Instead of each function working from separate lists, create a single Go-To-Market account portfolio informed by revenue potential and engagement signals. 
• AI can dramatically accelerate research, content personalization, and account list building, but only if you have a clear strategy first. Many companies are underutilizing AI or using it without a defined goal, leading to mediocre results.

Chapters

00:00 - Introducing Davis Potter, Founder of ForgeX

08:00 - Quick Coldplay Concert Conundrum Recap

10:00 - Davis’ first ABM Webinar horror story

16:00 - Redefining Account-Based Marketing: Beyond the traditional pyramid

18:00 - A new ABM segmentation model

24:00 - The case for a unified Go-To-Market account portfolio

27:00 - Growth ABM tactics that actually scale

31:00 - Where AI fits into an ABM strategy  (and where it doesn’t)

39:00 - How shadow AI is reshaping GTM

45:00 - Reporting, the board deck problem, and the MQL hangover

49:00 - What your Revenue Team needs to measure in modern ABM

53:00 - Replacing the Market Qualified Lead industrial complex

Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/

Epic Quotes

• “One practitioner can't cover 50 accounts and actually leverage one-to-one.” - Davis Potter

Connect with Davis

• LinkedIn: https://www.linkedin.com/in/davispotter62/ 
• ForgeX Website: https://www.forgex.ai/ 
• Revenue Xchange: https://open.spotify.com/show/7v2449do8UGuLAbilezi29?si=1a56c9a9a18d4550 

Shoutouts

• Demandbase
• Sangram Vajre: https://www.linkedin.com/in/sangramvajre/
• Sam McKenna: https://www.linkedin.com/in/samsalesli/ 
• Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge 
• Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ 
• Dan Gottlieb’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• Kerry Cunningham: https://www.linkedin.com/in/kerrycunningham/ 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 

Jon Miller’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in