The Transaction

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

The landscape of go-to-market in the B2B SaaS world is shifting rapidly, but thankfully we’ve got just the person to help you get ahead and innovate.James Kaikis is the Founder of GTMshift, Co-Founder of SolutionExec, Co-Founder of AI Sales Studio, and Host of The GTMshift Interview Series. James joins Matt Amundson and Craig Rosenberg to unpack the evolving role of sales reps, how to use the GTM Innovator’s Framework to stay up on AI advances, and why B2B SaaS companies must refocus their GTM motions on their customers.Plus, James shares his top spots to eat in Chicago.Also, Craig calls Matt a technical buyer, Matt rates Craig’s follicular health, and Producer Sam forgets how math works. Critical 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!

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

Surprise: Doing ‘more with less’, doesn’t actually work in B2B marketing, and today’s guest has the data to show it.Omar Akhtar is the Founder and Principal Analyst of Benchmarker and the Director of Content at UserTesting. Omar joins co-hosts Matt Amundson & Craig Rosenberg to dive into the B2B marketing data from Benchmarker’s latest survey, why the most successful companies are spending more on brand than demand, and how events have emerged as one of the top growth channels in go-to-market.Plus, Omar digs into when to prioritize paid versus organic channels in your marketing mix.Also, Craig outlines the plans for his kid’s booze-fueled birthday party, Matt laughs at an inopportune moment, and Producer Sam says ‘raccoon’. Critical TakeawaysDoing 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.Chapters00:00 - Episode Preview01:23 - Introducing Omar Akhtar, The Founder of Benchmarker03:54 - A Perilously Precipitous Sales Call06:01 - How Omar Moved From Rockstar to B2B Marketing Analyst12:26 - Craig’s Dog Crashes the Party in Multiple Ways13:32 - What Benchmarker’s Data has Revealed about Successful B2B Marketing Teams21:26 - Why the Best Marketing Teams are Spending More on Brand Marketing23:56 - Where Content Marketing Fits in the Modern B2B Marketing Mix30:34 - Events & Small Dinners are Converting Like Crazy, but Please Don’t Overdo Them37:24 - No Amount of Great Marketing Can Overcome a Crap Product, Have a Good Product & Execute the Basics of Marketing Well44:11 - What Makes Clay’s Marketing So Special50:21 - How Gong Survived the Latest SalesTech Revolution & is Now ThrivingJoin 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 AkhtarConnect with OmarLinkedIn: https://www.linkedin.com/in/omarbilalakhtar/ Benchmarker Website: https://www.benchmarkerdata.com/ UserTesting Website: https://www.usertesting.com/ ShoutoutsAmy 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!

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

For our first episode of the new year, we’re thrilled to welcome special guest Kathy Macchi,  the Executive Vice President, Innovation & Co-Founder at Inverta.Kathy joins co-hosts Craig Rosenberg & Matt Amundson to discuss where so many go-to-market leaders go wrong with their segmentation, why your message matters more than the channel you deliver it through, and how to design a successful mid-market marketing org amidst massive pressure for budget cuts.Also, Craig bemoans eating vegetables, Matt gives an update on Craig’s health, and some may have been kidnapped at Producer Sam’s house. Critical TakeawaysBefore 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.Chapters00:00 Harrowing Health Foods, Rave Recaps, & Tennis Talk08:30 Introducing Kathy Macchi, Co-founder at Inverta12:40 The Business Concerns Coming up In CMO Councils, Primarily AI & Budget Cuts18:43 Why Cultivating Good Taste Transcends AI Advancements & Solving The Problem Before Adding AI Tools30:27 AI's Impact on B2B Marketing Jobs and Economy32:37 Rethinking Marketing and Business Processes with AI34:06 The Role of Effective Targeting for Account-Based Marketing in the AI-era37:02 Effective Use of AI in Marketing42:13 Messaging + B2B Marketing Channel Strategies and Multi-Channel Marketing53:04 B2B Sales and Territory PlanningJoin 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 RosenbergConnect with KathyLinkedIn: https://www.linkedin.com/in/kathy-macchi-aa148b/ Inverta Website: https://www.inverta.com/ ShoutoutsGeoffrey Moore: https://www.linkedin.com/in/geoffreyamoore/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Carlos AlcarazDavid Boskovic: https://www.linkedin.com/in/dboskovic/ Our Episode with David: https://open.substack.com/pub/thetransaction/p/building-an-ai-first-go-to-marketOmar Akhtar: https://www.linkedin.com/in/omarbilalakhtar/Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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

If you feel like your pipeline is broken, your CAC is bloated, and your dashboards are lying to you… you’re FAR from the only one. Joining the show are the Metrics Brothers, Ray Rike and Dave Kellogg! Ray is the Founder & Chief Evangelism Officer of Benchmarkit, Host of Metrics That Measure Up, a Founding Member of the SaaS Metrics Standards Board, and is an LP at Stage 2 Capital.Dave co-hosts The Metrics Brothers Podcast, writes the incomparable ‘Kellblog’, and is an EIR at Balderton Capital.Dave and Ray join co-hosts Matt Amundson and Craig Rosenberg to discuss the importance of brand investment in the AI age, overcoming the pipeline generation crisis in B2B SaaS, and how GTM leaders can drain the “metrics swamp.”Plus, Dave divulges which SaaS metrics he finds loathsome and Ray shares his unique method for calculating Marketing CAC.Also, Craig airs an ambrosia-related grievance, Matt unveils an old school tactic he’s still using, and Producer Sam falsely announces an exclusive scoop on The Transaction. Critical TakeawaysTreat 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. Chapters00:00 Episode Preview01:48 Introducing Ray Rike and Dave Kellogg, The Metrics Brothers05:40 How GTM Leaders can Escape from their ‘Dashboard Hell’11:08 Which Metrics Matter to Your Board18:37 Overcoming The B2B SaaS Pipeline Crisis24:38 The Difference Between Search Engine Optimization & Answer Engine Optimization29:52 Why Brand Still Matters in the age of AI & How to Measure Brand45:21 Why B2B Marketers Need to Measure both Opportunity Count & Cost Per Opportunity47:38 Why Pipeline Coverage Ratio is so Critical for B2B SaaS Startups51:21 Examining Tantalus & The Cultural Impact of Ambrosia in All of Its FormsJoin 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 KelloggConnect with Ray & DaveRay’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/ ShoutoutsRay’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:

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

With so much attention within the go-to-market world paid to marketing and sales, account management, which is arguably just as important, rarely gets its due.Alex Raymond is the Founder of AMplify and Host of the Account Management Secrets podcast. Alex joins co-hosts Matt Amundson and Craig Rosenberg for the first major discussion on the podcast of account management and its crucial role in growing revenue and overall company value for SaaS vendors. Plus, Alex breaks down how CROs should organize their team, what types of people make for the best account managers, and why in-depth stakeholder mapping of customer accounts is so critical to growing revenue. Also, Craig mixes up country singers, Matt discovers a great path, and Producer Sam compares someone’s comment to military ordinance. Critical TakeawaysAccount 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.Chapters00:00 - Episode Preview01:00 - Trouble with Tickets03:44 - Introducing Alex Raymond, Founder of AMplify05:59 - The Role of Account Management in The Growth of B2B Startups12:27 - The Power of Exponential Thinking for Entrepreneurs16:01 - A Quick Sidebar about Business Events and Dining in Boulder19:31 - Why Account Management is a Revenue Function & When Your Startup Needs Account Managers29:15 - Where Account Management Should Fit in Your Revenue Team’s Organizational Design 36:26 - What To Look for When Hiring Great Account Managers42:03 - When Account Managers Should Be Brought into New Deals49:13 - Developing Complex Stakeholder Maps for Customer AccountsJoin 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 AmundsonConnect with AlexLinkedIn: https://www.linkedin.com/in/afraymond/ Website: https://www.amplifyam.com/ Podcast: https://www.amplifyam.com/podcast ShoutoutsCraig’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!