Episodi

  • Organizing Unforgettable Events for B2B with Jen Igartua, CEO of Go Nimbly - Ep 81

    Organizing Unforgettable Events for B2B with Jen Igartua, CEO of Go Nimbly - Ep 81
    Jun 11 2026
    Back for her second episode is the one and only Jen Igartua, the CEO of Go Nimbly and RevOps OG. Jen joins Co-Hosts Craig Rosenberg and Matt Amundson to break down what made Go Nimbly’s Rev Fest such an incredible event for everyone, from the GTM leaders attending to the speakers, and even the sponsor brands. Jen outlines why she picked a truly iconic venue for a business event, how she prepared the speakers to deliver insights entertainingly, and what B2B event sponsors should be doing instead of popping up another tired booth.Plus, Jen shares how business leaders should approach orchestrating workflows with new AI tools.Also, Craig plans his next tattoo, Matt earns a B-minus, and Producer Sam complains about ugly wood paneling. Critical TakeawaysThe secret to hosting an amazing B2B event is to stop copying tired event formats and instead build from your genuine passions. GTM leaders should audit their planned events and ask: "What would I genuinely love to attend?" If the honest answer doesn't match the event they're building, they should redesign it. Authenticity is the differentiator, and audiences can tell immediately when passion is faked.Treat your event like you’re putting on a show, not just another business conference. For example, Jen hired Doug Landis as a presentation coach, opened the venue a day early for speaker training, and had MCs introduce speakers so presenters could lead with their content immediately rather than wasting audience attention on bio slides. This "show vs. conference" framing forces event organizers to make logistical decisions to serve the audience experience rather than operational convenience.Rev Fest did not rely on “great speakers” and hope for the best. The 20-minute cap, speaker coaching, rehearsal time, MC intros, and topic curation all turned content into something attendees could actually stay locked into instead of politely enduring.To move your team from "random acts of AI" to orchestrated workflows, start by mapping out your current processes and identifying which steps are truly automatable versus which require judgment. Jen's framework is to define the end-to-end job-to-be-done first and then deploy AI as one component inside that designed workflow. When documenting your processes, clearly address who does what, where human judgment is needed, where full automation is possible. The companies that deployed technology last but got their strategy and process right first are consistently the most tech-forward (and successful) in practice. GTM leaders being pressured to "become AI-first" should resist the impulse to start with tools and instead start with their most important business outcomes, work backwards to the workflow changes required, and then identify where AI fits.Rather than vendor booths, Jen designed facilitated "table talks" where sponsors ran small-group discussions on topics the audience had already said they cared about. Critically, she required sponsors to bring senior operators (not AEs), trained them on facilitation techniques, and sent post-event notes with everyone's LinkedIn to all attendees.Chapters00:00 Episode Preview02:50 Introducing Jen Igartua, CEO of Go Nimbly06:50 What Made Go Nimbly’s RevFest One of the Best Go-To-Market Events11:53 A Dog-Leg about Ham Legs and Spanish Film Studies 20315:27 Thinking Bigger than a Business Conference To Create a Show19:54 Picking a Truly Unique Venue & Setting the Right Vibes for Your Event23:48 Actually Interesting Event Sponsor Table Talks System28:46 Forward Thinking Companies are Done with Random Acts Of AI32:07 Defining AI Orchestration & What Marketing Tasks to Automate First46:29 Business Processes First, AI Tool Implementation Second49:33 Rev Ops Workflows And EnrichmentJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“The really great stuff doesn't scale. Stop trying to scale it.” - Jen Igartua“You’ve got to make the stuff you love. Like, why are you creating something that you are not into?” - Jen IgartuaConnect with JenLinkedIn: https://www.linkedin.com/in/jen-igartua/ Go Nimbly Website: https://www.gonimbly.com/ ShoutoutsJamón Jamón (Dir. Bigas Luna, 1992)Javier Fesser: https://www.imdb.com/name/nm0275250/?ref_=nv_sr_srsg_0_tt_0_nm_8_in_0_q_fesser Campeones (Dir. Javier Fesser, 2018)Champions (Dir. Bobby Farrelly, 2023)House of Yes: https://www.houseofyes.org/ Ruslan Tovbulatov: https://www.linkedin.com/in/ruslan-tovbulatov/ Doug Landis: https://www.linkedin.com/in/douglandis/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    59 min
  • The AEO Playbook: Own the AI Shortlist - Live with Sydney Sloan at GTM Tailwinds - Ep 80

    The AEO Playbook: Own the AI Shortlist - Live with Sydney Sloan at GTM Tailwinds - Ep 80
    Jun 8 2026

    Sydney Sloan, the CMO of G2, joined Craig, Matt, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording where she outlined the major shift in B2B buyer behavior, how to measure and track Answer Engine Optimization, and why the partnership and distribution layer is as important as content creation.


    Critical Takeaways

    • Over half of B2B buyers (51%, up from 24% just one year ago) now start their research in an LLM rather than Google. GTM leaders must treat AI answer engines as the new top-of-funnel, not a novelty. Waiting another year means your competitors get a 12-month head start on owning these answers.
    • Stop writing for search crawlers, instead write for the person you're trying to influence. The old HubSpot model of casting a wide content net (writing for non-marketers to drive traffic) is losing effectiveness. Instead, teams should map out the specific jobs-to-be-done for each buyer persona, the product leader, the CFO, the practitioner, and write questions and answers directly for that person. This persona-centric content approach is what gets surfaced and cited in LLM responses.
    • LLMs favor content that mirrors the structure of a question, such as FAQs, pro/con lists, pricing comparisons, and definitional formats. G2 proactively added pricing data and pro/con lists to every product profile after seeing those formats show up in prompt patterns six months earlier. GTM teams should audit their top-performing SEO pages and rewrite AEO versions with this structure immediately.
    • Publications like Forbes and VentureBeat are now formal citation sources for LLMs. G2 counter-pitched a negative MIT AI study and earned significant coverage, which then got indexed and cited. Teams should re-engage PR agencies (if they have newsworthy content) and consider low-cost options like Forbes Council ($1,600/year) to establish founder brand as authenticated content on authoritative domains.


    Chapters

    00:00 Episode Preview

    00:42 Introducing Sydney Sloan, the CMO of G2

    01:25 Focus Wins at SalesLoft

    03:01 AEO vs GEO Explained

    04:00 New Buyer Research Behavior

    05:18 Build Brand in LLMs

    06:44 AI Citations of Reddit and G2

    09:30 Zero to One AEO Setup

    10:10 Content Engineering Playbook

    11:58 G2 Adapts to Prompt Trends

    13:50 Measuring AEO Impact

    17:29 Consensus Signals and Sentiment

    19:37 Bots vs Humans Traffic

    20:14 Own Citation Sources

    21:07 Reddit and Influencers

    22:32 Freshness vs Old Content

    23:51 Pruning Content for LLMs

    25:01 PR Is Cool Again in B2B Marketing

    27:02 Should Founders Hire PR

    28:57 Partnerships and Frenemies

    33:07 AEO and SEO Together

    34:40 LinkedIn Virality Tips

    35:43 Wrap Up and Outro

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


    Epic Quotes

    • “AI's changed everything. Including where your buyers go to do their research, discovery, and shortlisting.” - Sydney Sloan


    Connect with Sydney Sloan

    • LinkedIn: https://www.linkedin.com/in/sydsloan/
    • G2 Website: https://www.g2.com/


    Shoutouts

    • GTMshift: https://gtmshift.com/


    Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    36 min
  • Attention is the New Moat - LIVE with Scott Albro at GTM Tailwinds - Ep 79

    Attention is the New Moat - LIVE with Scott Albro at GTM Tailwinds - Ep 79
    Jun 1 2026

    The one and only Scott Albro once again returns to The Transaction, but this time, Scott joined Craig, Matt, James Kaikis, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording. Scott shares his insights on how to overcome the real GTM problem of the ‘attention bottleneck’ and lays out a precise framework for flipping from push to pull using network thinking, transformation narratives, and high-leverage distribution tactics.


    Using real examples from Clay, Granola, and ServiceTitan, he shows exactly how to identify 10x hubs in your market, build a narrative that makes your customer the hero, and develop a founder brand strategy that creates category synonymy rather than LinkedIn vanity metrics.


    Critical Takeaways

    • Just because you start a company, doesn’t mean anyone cares about it. GTM strategy has to start with the question, “How will this company earn attention in a market where AI has made product-building and content creation cheaper than ever?”
    • GTM leaders should map their market as a network to identify the "10x hubs" in their market, which are nodes that have outsized influence over target buyers, and deliberately influence those hubs with their narrative. This unlocks massive downstream reach that a standard approach to a target account list would not have surfaced.
    • Every startup needs three story types: the customer story (pain + day-in-life), the personal journey story (founder authenticity), and most importantly, the transformation story. The transformation narrative has three parts: the broken status quo, a believable-but-magical future vision, and a prescriptive guide for how customers get there.
    • A narrative must be big, differentiated, and believable simultaneously. Scott's three non-negotiable attributes for a winning narrative are that it must compete for attention in your specific market, it must say something nobody else is saying, and it must be proven in the product demo. Marketers should test every narrative draft against all three filters before taking it to market.


    Chapters

    00:00 - Session Preview Clip

    00:40 - Introducing Scott Albro & How Scott’s First Board Meeting with Craig Went

    04:58 - Why the Attention Bottleneck is a Crisis for Startups in an Ever-Crowded Market

    11:22 - How B2B Marketers Craft Winning Narratives That Spread Like Wildfire

    16:16 - Focusing Closer on Your Target Market Will Reveal The Compelling Narrative That Works For Your Buyer

    20:41 - Why & How Founders & CEOs Should Incorporate Their Own Authenticity into Their Narrative

    26:49 - Treating Your Market as a Network of Target Accounts, Not Just a Target Account List

    32:11 - Creating Systems for Founders and CEOs to Build Attention Around Your Brand Narrative


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


    Epic Quotes

    • “ In today's market, everything is downstream of attention.” - Scott Albro
    • “The default setting for a startup is obscurity.” - Scott Albro


    Connect with Scott

    • LinkedIn: https://www.linkedin.com/in/scottalbro/


    Shoutouts

    • GTMshift: https://gtmshift.com/
    • Nick Mehta: https://www.linkedin.com/in/nickmehta/
    • Gainsight: https://www.gainsight.com/


    Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    37 min
  • Building an Incorruptible Company that Lasts with Eric Ries, Author of Incorruptible & The Lean Startup - Ep 78

    Building an Incorruptible Company that Lasts with Eric Ries, Author of Incorruptible & The Lean Startup - Ep 78
    May 27 2026
    It’s not every day that you get to have one of the most important thinkers in the startup world on your podcast, but for The Transaction, that day is today.Eric Ries is a Founder and the renowned business author of The Lean Startup and his brand new book, Incorruptible: Why Good Companies Go Bad…and How Great Companies Stay Great.Eric joins Craig Rosenberg and returning guest host Scott Albro to discuss the forces that make companies vulnerable to destruction from within and without. Then he offers solutions that safeguard against them for the long-term.Incorruptible is the blueprint for companies that will prosper and endure without losing their soul. Plus, Eric shares how go-to-market teams, in their unique market-facing position, can make a profound impact on customer trust, both positively or negatively.Also, Craig describes his current deodorant situation, Scott mentioned the looming ARR creative accounting crisis, and Producer Sam mentions the link to Eric’s book in the show notes below. Critical TakeawaysTrust is the force that lowers friction, reduces costs, increases velocity, and makes customers stick around even when a company makes mistakes. By keeping their promises to customers, sales and marketing teams create long-term enterprise value by adding to the company’s trust account.A strong customer promise is not enough unless a company’s incentives, reporting, governance, and business model are built to defend it and deliver value to the customer.Corruption often looks like optimization in the moment. Eric defines corruption as “the making of money without the creation of value,” which many ‘best practices’ often encourage. Overpromising product capabilities, manipulating ARR, squeezing customer trust for quota, or turning a beloved product into an ad-clogged mess may improve a metric temporarily, but it destroys the value engine underneath.Go-to-market sits at the edge of the company’s moral logic. The GTM team is the “pointiest point at the edge of the spear” because it’s how the market experiences the company’s promises first. For example, revenue leaders are not just responsible for pipeline; they are responsible for making sure the promises used to create pipeline are believable, durable, and backed by the product and business model.Corporate governance is not about extra busywork or bureaucracy; it’s how companies, yes, even startups, protect what makes them worth building.Chapters00:00 - Episode Preview02:25 - Introducing Eric Ries, Author of The Lean Startup & Incorruptible06:09 - The Legacy of The Lean Startup in the AI Age08:59 - The Business Lessons Learned from Sol Price’s Journey of Founding FedMart & Price Club18:39 - How Founding The Long-Term Stock Exchange Showed The Limits of Best Practices & Conventional Thinking24:03 - How Businesses Cash in Trust & How They Build Trust with Customers27:54 - Why Re-examining OKRs & GTM Metrics Can Improve the Long-Term Health of a Company35:06 - The Looming Crisis in How Startups are Accounting their Annual Recurring Revenue (ARR) 40:10 - Why & When Early Stage Startups Need To Seriously Think About GovernanceJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ Trust is the asset that compounds.” - Eric Ries“ A lot of these so-called best practices are actually value destroying.” - Eric RiesConnect with Eric LinkedIn: https://www.linkedin.com/in/eries/ Incorruptible on Amazon: https://www.amazon.com/Incorruptible-Shape-Companies-That-Stand/dp/B0FWZZBPZB Website: http://incorruptible.co ShoutoutsLenny’s Podcast: https://www.lennysnewsletter.com/podcast Matt Dixon: https://www.linkedin.com/in/matthewxdixon/ Brent Adamson: https://www.linkedin.com/in/brentadamson/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    44 min
  • Using AI to Empower SDRs & Eliminate Admin Work with David Wilkins, Founder of SDR Leaders of EMEA & B2B Sales Expert - Ep 77

    Using AI to Empower SDRs & Eliminate Admin Work with David Wilkins, Founder of SDR Leaders of EMEA & B2B Sales Expert - Ep 77
    Apr 16 2026
    Excessive admin work and poor-performing sales plays are killing SDR effectiveness and, in turn, company growth. We just so happen to know just the B2B sales expert to help SDR leaders kick things up a notch, wherever they may reside around the globe.Besides having a wonderful British accent, which Craig loved, David Wilkins is the Founder of SDR Leaders of EMEA and the Co-Founder of SDR Leaders of USA and APAC. David joins Co-Hosts Craig Rosenberg and Matt Amundson to dig into how sales leaders are overcoming the major issues facing SDRs (Sales Development Reps) in B2B sales today. David shares how successful sales leaders are implementing AI tools to cut down on excess admin work for their SDRs, why sales channels like cold-calling & video messages are outperforming email outreach, and how dialing up the difficulty of the sales training for your reps can keep them cool as can be on even their most cantankerous sales calls.Plus, David outlines the totally standard, run-of-the-mill journey of how he went from studying at the second-worst university in the UK to working for the number-one mayonnaise manufacturer in the Netherlands and ended up getting into B2B sales. Also, Craig references a late-80s rap duo, Matt alludes to the promise of a brisket, and Producer Sam somehow manages to ask a decent salestech question after breaking the 4th wall earlier in the episode.Critical TakeawaysExcessive admin work is still eating the SDR role alive. In a surprising number of B2B companies, SDRs are still burning three-plus hours a day on manual admin tasks. That is not harmless busywork in B2B sales; it is precious selling time being quietly set on fire. Rather than replacing a human SDR with an AI avatar, target this admin & sales prep work for elimination with AI. Email-first outbound has run out of runway. Email still has a place, but it should be just one piece of a larger outbound strategy that focuses more heavily on better-performing tactics like cold calls and social media touchpoints. The practical implication for sales and marketing leaders is simple: email can support the motion, but it cannot be the whole motion anymore.Sending videos and voice notes through LinkedIn messages works because they do something most outreach still does not: they make it obvious a real, honest-to-goodness human being is on the other end. That is especially useful in B2B SaaS, where copy-paste messages have saturated email, text, and even DM inboxes, and being able to interrupt that pattern buys sellers the few seconds of attention they need to make inroads.The sales training you provide for your SDRs and AEs should be significantly harder than anything they might deal with on a standard sales call. That way, if they find themselves in a delicate situation, they have the skills to stay calm and continue moving the conversation forward. A great way to give your sales reps more, well, reps is to use a training tool with AI-avatars of different customer profiles in sales scenarios.Chapters00:00 - Episode Preview00:51 - Trans-Atlantic Holiday Customs and Re-Ranking of Meats 04:11 - Introducing David Wilkins, Founder of SDR Leaders of EMEA & B2B Sales Expert06:55 - David's Journey From a Terrible School to Amazing Mayo & Eventually a B2B Sales Job15:10 - Why SDR Leaders Don't See Headcount as The Solution for Success with Sales Development in B2B SaaS 30:18 - Why Cold-calling Beats Email for Engaging with Prospects34:59 - Video Messages & Voice Notes Break the Pattern of B2B Sales Outreach46:09 - Improving Sales Training with AI Avatars To Help SDRs Perform Better on Sales Calls49: 57 - Predicting the Future Evolution of the SDR Role in B2B Sales & GTM55:04 - Random Rap & Wrestling References Before Wrapping UpJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“ Make the training harder than the game.” - David Wilkins“ Making this function what it is, which is a critical part of the revenue generating organization.” - David Wilkins“ I'm gonna be calling myself Ron now, if ever I get in trouble” - Ron DavidsonConnect with DavidLinkedIn: https://www.linkedin.com/in/daveewilkins/ SDR Leaders of EMEA Website: https://sdr-leader.com/ ShoutoutsLars Nilsson: https://www.linkedin.com/in/lanilsson/ Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales?utm_campaign=post-expanded-share&utm_medium=web Travis Henry: https://www.linkedin.com/in/travisjhenry/ Russell Hearl: https://www.linkedin.com/in/russhearl/ PG.aiTitanXNooksHiya Morgan Ingram: https://www.linkedin.com/in/morganjingramamp/ QuibblySynthesiaTavusHyperboundScott AlbroRodney-O & Joe Cooley: https://youtu.be/BynWb6swQ74?si=_7ykfGXyz0GDACRl Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    58 min
  • Building a Movement Through B2B Marketing with Kacie Jenkins, Head of Marketing for Claude Code at Anthropic - Ep 76

    Building a Movement Through B2B Marketing with Kacie Jenkins, Head of Marketing for Claude Code at Anthropic - Ep 76
    Mar 31 2026
    Kacie Jenkins is the Head of Marketing for Claude Code at Anthropic. Prior to joining Anthropic, Kacie led marketing at Sendoso as SVP of Marketing, Sourcegraph as VP of Marketing, and Fastly as VP of Marketing, to name a few.Kacie joins co-hosts Craig Rosenberg and Matt Amundson to unpack what B2B brands need to learn from B2C companies in order to build bold, unforgettable brands that increase revenue and redefine markets. Plus, Kacie outlines why B2B startups need to see building a founder brand as a pipeline engine, how to move beyond broken marketing attribution systems, and why brand marketing is making a massive comeback.Also, Kacie shares the outcome of all her speakers getting food poisoning before an event, Craig explains why he’s bringing his son to Vegas, and Matt states his stance on the existence of ghosts. Critical TakeawaysFounder-led brand and content works because buyers want conviction from the people shaping the company, not just polished messaging from the brand account. The key to building a strong founder brand is finding the intersection of three things: 1. What is the founder an expert at? 2. What makes the founder utterly unique? 3. What does the target audience want and need?A bold brand doesn't mean punching competitors; it means being so weird, human, and mission-driven that people can't stop thinking about you. At Fastly, this meant leaning into engineer culture with quirky campaigns (literal messenger pigeons), bright red branding mirroring the founder's personality, and taking public stands on internet ethics. Find what makes your company authentically different and lean all the way into it.Your founder is the person with the most conviction on your team, and that conviction is what cuts through noise in crowded categories. Marketing should treat building and amplifying the founder's narrative as a top priority, not a side project. Invest time sitting with the founder to uncover what they stand for, what they hate, and what future they're building — then help them show up consistently.Sales leaders should map executive posts, thought leadership clips, and campaign creative to relevant strategic accounts, then use that content to multi-thread and re-engage deals. When a founder or visible executive has market credibility, reps get warmer entry points and stronger follow-up moments.Values only count when customers can feel them. If the brand story stops at messaging, buyers will eventually spot the gap. For example, Fastly’s brand worked because their stance showed up in customer selection, customer success, and even how they defined who they wanted to win with in the market.Chapters00:00 - Episode Preview00:51 - Spooky Baseball02:20 - Introducing Kacie Jenkins, Head of Marketing for Claude Code at Anthropic05:46 -  Accidentally Hosting a Spooky Customer Advisory Board Retreat12:53 - What Happens When All Your event Speakers get Food Poisoning19:03 -  How Founders Can Seize the Story of Their Category and Own The Narrative35:48 - How to Build Bold Brands for B2B SaaS41:22 - Why brand fails without founder buy-in47:23 - Marketing Attribution is Broken. Now what?Join our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“The key to winning is real, true, authentic differentiation.” - Kacie JenkinsConnect with KacieLinkedIn: https://www.linkedin.com/in/kaciejenkins/ Anthropic Website: https://www.anthropic.com/ Claude Code Website: https://claude.com/product/claude-code ShoutoutsRuby James: https://www.linkedin.com/in/rubyjameslinkedin/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Artur Bergman: https://www.linkedin.com/in/crucially/  Katie Penner: https://www.linkedin.com/in/kathrynpenner/ Kris Rudeegraap: https://www.linkedin.com/in/rudeegraap/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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    58 min
  • 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 min
  • 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 min