The Transaction Podcast Por Craig Rosenberg & Matt Amundson | B2B Sales & Marketing Experts - Hosts of The Transaction arte de portada

The Transaction

The Transaction

De: 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 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. 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.The Transaction Economía
Episodios
  • How Courageous Marketing Leadership Builds Bold Brands with Udi Ledergor, Chief Evangelist at Gong - Ep 75

    How Courageous Marketing Leadership Builds Bold Brands with Udi Ledergor, Chief Evangelist at Gong - Ep 75
    Mar 17 2026
    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 TakeawaysWhen 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.Chapters00:00 - Episode Preview00:56 - Craig Flounders While Filibustering to Find an Excuse For His Profile Photo Fiasco03:16 - Introducing Udi Ledergor, Chief Evangelist at Gong05:46 - 3 Critical Marketing Lessons Learned from an Email Campaign that Almost Ruined a Massive B2B SaaS Brand17:02 - How Gong Intentionally Built an Authentic, Sincere, & Human Brand for A B2B SaaS Startup22:06 - Reimagining B2B Marketing Events To Optimize for Guest Experience28:48 - Using AI as a Quality Filter for Marketing Ideas33:36 - The Two Ways to Use AI in Your Work35:19 - Where Gong Lands in the Gated-versus-Ungated Content Debate45:26 - The Basics of Email Marketing That Still Work in B2B47:45 - The Bait & Switch Twitter Play for Boosting Web Traffic For Startups51:31 - How Gong Develops its Content Marketing and Distribution Strategy TogetherJoin 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 LedergorConnect with UdiLinkedIn: 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/ ShoutoutsRuby 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/...
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    59 m
  • Positioning Needs to Underpin Every Part of Your Brand Strategy with Stacey Epstein, CEO of Structured - Ep 74

    Positioning Needs to Underpin Every Part of Your Brand Strategy with Stacey Epstein, CEO of Structured - Ep 74
    Feb 26 2026

    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/
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    55 m
  • The AI-Enabled Future of Sales with James Kaikis, Founder of GTMshift - Ep 73

    The AI-Enabled Future of Sales with James Kaikis, Founder of GTMshift - Ep 73
    Feb 9 2026
    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 TakeawaysTechnical 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 SceneJoin 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 JamesLinkedIn: 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 ShoutoutsDoug 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 ...
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    1 h y 3 m
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