The Transaction

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!

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!

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/rebuilding-b2b-customers-confidenceKyle Lacy: https://www.linkedin.com/in/kylelacy/ Top Swear Words - Gong: https://www.gong.io/blog/how-cursing-impacts-sales Alec Paul: https://www.linkedin.com/in/alecjpaul/ Alec’s Episode: https://open.substack.com/pub/thetransaction/p/becoming-a-linkedin-master-with-alec Danny Hutto: https://www.linkedin.com/in/dannyhutto/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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 TakeawaysBefore you start executing any marketing tactics, you need to develop a strong positioning framework that clearly articulates what your company does, why it matters, who the buyer is, and what makes you different. Way too many B2B companies are still doing "random acts of marketing" where every campaign differs from the website messaging, creating inconsistent brand experiences that confuse buyers and dilute impact.As AI handles more aspects of content creation, campaign distribution, and administrative tasks, marketing teams should prioritize hiring "tastemakers" who demonstrate exceptional judgment in evaluating strategic creative decisions. The ability to curate, refine, and elevate work, whether human-made or AI-generated, matters more than the ability to execute tactical tasks manually.Treat your S-1 as the foundation for all Go-To-Market activities. It should be the basis of your positioning, informing everything from why you exist, what your product does, points of competitive differentiation, and your future visionOrganizations need a centralized AI leader, whether in marketing ops, revenue ops, or IT, to coordinate AI initiatives across functions and prevent teams from burying themselves in disjointed AI projects. This role ensures strategic alignment, prevents redundant tool purchases, and helps teams focus AI adoption on high-impact use cases rather than experimenting randomly.Chapters00:00 - Episode Preview00:42 - Craig’s Story of Endings and New Beginnings02:46 - Introducing Stacey Epstein, CEO of Structured07:16 - Accidentally Sending an Embarrassing Email to Every Co-worker in an Entire Region15:34 - Why Positioning is Foundational to Your Brand and Storytelling21:29 -  How to Get Better Input on Marketing from Founders & CEOs31:58 - What Stacey's Learned about AI From Hosting her Podcast34:54 - Why You Need to Hire “Taste Makers” in an AI-first world41:50 - A Brief Aside on the Etymology of Czar/Tsar43:35 - Why Companies are Hiring GTM Engineers & The Impact They're Having45:58 - How to Lead AI Implementation in Your CompanyJoin 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 EpsteinConnect with StaceyLinkedIn: https://www.linkedin.com/in/staceyepstein/ Magnetic GTM Website: https://www.magneticgtm.com/ Podcast: https://aivegotquestions.buzzsprout.com/ Structured Website: https://structured.ai/ ShoutoutsDavid Boskovic: https://www.linkedin.com/in/dboskovic/ David’s Episode: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-marketLisa Cole: https://www.linkedin.com/in/lisacole01/ 

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 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!