The Transaction

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!

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!

Ray Rike, Founder of Benchmarkit and a B2B SaaS metrics guru, joins industry veteran Dave Kellogg, co-host of The Metrics Brothers podcast, to tackle the frustrations of B2B SaaS metrics. They discuss overcoming dashboard chaos and the pipeline crisis, emphasizing the importance of a unified metrics framework. Ray reveals his method for calculating Marketing CAC, while Dave shares his disdain for certain SaaS metrics. The duo advocates for branding investment and answer engine optimization as keys to thriving in the AI-driven era.

In this engaging discussion, Alex Raymond, founder of AMplify and host of the Account Management Secrets podcast, reveals the often-overlooked power of account management in driving SaaS revenue. He emphasizes that account management should be viewed as the growth department, advocating for proactive account expansion instead of reactive support. Alex shares insights on building account management capabilities early, ideal profiles for account managers, and the need for a structured approach to customer growth. Prepare for a mix of valuable strategies and lighthearted banter!

Gabe Larsen, Chief Revenue Officer at Signals and former CMO at Kustomer, dives into the world of agentic AI and its impact on signal-based marketing. He critiques traditional Account-Based Marketing, revealing how AI can enhance customer engagement through omni-channel execution. Gabe shares his views on the challenges of building vs. buying AI tools and suggests that flexible vendor solutions will dominate. He also discusses the future of AI pricing, advocating for salary-based models for agentic employees, envisioning a shift from tools to cloud-based teammates.

The vast majority of companies that think they are running ABM (Account-Based Marketing) are not actually running ABM. Not only that, they wouldn’t recognize a real ABM strategy if one came up and slapped them in the face with a stack of direct mailers.Davis Potter is the CEO & Co-Founder of ForgeX, a research and advisory firm that helps B2B companies modernize their Account-Based Go To Market and AI strategies. Davis joins co-hosts Matt Amundson and Craig Rosenberg for an exploration of the current state of ABM (Account-Based Marketing), what it takes to drive impact of using AI in GTM Execution, and how to right-size the B2B marketing tactics to each account. Also, Craig uses a ‘Matt-ism’, Matt distinguishes cuddling from canoodling, and Producer Sam fixes a problem with his face. Critical TakeawaysThere are three core account-based marketing models: Enterprise ABM (1:1 and 1:few), Growth ABM (1:many at scale), and Deal Acceleration (targeted support for individual opps).Shift from short, one-off marketing campaigns to holistic, always-on programs that run continuously throughout the year. Build a playbook of ABM tactics (e.g., webinars, executive dinners, personalized landing pages, LinkedIn ads) and deploy them based on account tier and industry segment. This enables ongoing engagement and better adapts to complex B2B buying cycles.Select and tier accounts based on informed revenue potential, not just logo desirability or gut feel. Analyze first, second, and third-party signals, as well as customer LTV and microsegments, to prioritize accounts for deeper personalization and resource allocation. For example, reserve direct mail and executive engagement for tier one, while using scalable digital tactics for lower tiers.Unify your target account lists across sales, marketing, and customer success to drive alignment and efficiency. Instead of each function working from separate lists, create a single Go-To-Market account portfolio informed by revenue potential and engagement signals. AI can dramatically accelerate research, content personalization, and account list building, but only if you have a clear strategy first. Many companies are underutilizing AI or using it without a defined goal, leading to mediocre results.Chapters00:00 - Introducing Davis Potter, Founder of ForgeX08:00 - Quick Coldplay Concert Conundrum Recap10:00 - Davis’ first ABM Webinar horror story16:00 - Redefining Account-Based Marketing: Beyond the traditional pyramid18:00 - A new ABM segmentation model24:00 - The case for a unified Go-To-Market account portfolio27:00 - Growth ABM tactics that actually scale31:00 - Where AI fits into an ABM strategy  (and where it doesn’t)39:00 - How shadow AI is reshaping GTM45:00 - Reporting, the board deck problem, and the MQL hangover49:00 - What your Revenue Team needs to measure in modern ABM53:00 - Replacing the Market Qualified Lead industrial complexJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“One practitioner can't cover 50 accounts and actually leverage one-to-one.” - Davis PotterConnect with DavisLinkedIn: https://www.linkedin.com/in/davispotter62/ ForgeX Website: https://www.forgex.ai/ Revenue Xchange: https://open.spotify.com/show/7v2449do8UGuLAbilezi29?si=1a56c9a9a18d4550 ShoutoutsDemandbaseSangram Vajre: https://www.linkedin.com/in/sangramvajre/Sam McKenna: https://www.linkedin.com/in/samsalesli/ Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan Gottlieb’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Kerry Cunningham: https://www.linkedin.com/in/kerrycunningham/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon Miller’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in 

Rachel Dines, an advisor and former Forrester analyst, dives into the crucial world of analyst relations for SaaS startups. She emphasizes the importance of building genuine relationships with analysts before spending on subscriptions. Rachel shares her insights on focusing on a single use case to streamline go-to-market strategies and insists that the first marketing hire should be a product marketer for effective messaging. Plus, she recounts a humorous career advice mishap. Tune in for invaluable tips and entertaining banter!

Even with all the newest, shiniest AI tools out there, successful, sustainable B2B sales growth is still built on nailing the basic sales skills.To provide a refresher on those basic B2B sales skills and more, we’re thrilled to introduce Tom Murtaugh, the Portfolio Operations Director at Nordic Capital, a leading sector-specialist private equity firm. Tom joins co-hosts Craig Rosenberg and Matt Amundson to discuss the importance of maintaining deal control, why revenue leaders need to understand the key activities that drive outcomes, and how to get your sales managers up to speed as they become more valuable with the implementation of AI.Plus, Tom helps Craig and Matt perform an autopsy on the failure of the sales enablement movement.Also, Craig once again references TOPO and Matt gets envious of a warm male embrace while also imparting the joys of parenthood.Critical TakeawaysWhat are the handful of activities that have a real impact on moving a deal forward for your company? While most organizations cannot empirically state which activities drive revenue, using modern data tools and call analysis, sales leaders can and should run correlation analyses to pinpoint and scale what top performers do.Sales leaders should be directly involved in late-stage enterprise deals, ensuring there is a clear, actionable joint execution plan for each opportunity. Top-down focus and hands-on deal reviews with sales leaders is critical to exceeding targets, even when the forecast looks grim. This level of engagement cannot be delegated or replaced by process alone.AI can accelerate analysis and experimentation, but it cannot define your core GTM motions or fix broken processes. If you haven’t figured out what works, AI will only amplify confusion. Go-To-Market leaders must first establish and validate the key behaviors and activities that move the needle before layering on automation or analytics. Sustainable revenue growth comes from robust GTM infrastructure, such as processes, platforms, and RevOps, that persist beyond any single CRO or sales leader.Sales enablement programs often fail when led by people without quota-carrying experience, devolving into classroom-style training that sellers reject. Shift to “sales excellence” roles, where former sales leaders who coach reps in the field, ride along on calls, and provide practical, trusted guidance. The most powerful enablement tools are those that let reps learn directly from top performers, such as reviewing Gong calls or shadowing high achievers. Tom shared that new reps who proactively sought out and emulated top sellers ramped faster and performed better. Make it easy for your team to access and learn from real sales conversations, not just static content.Chapters00:00 - Episode Preview03:51 - Introducing Tom Murtaugh, Portfolio Operations Director at Nordic Capital10:09 - How Improving Deal Control Turned Around a Terrible Quarter for Collibra21:02 - Understanding the Key Activities that Really Drive Outcomes in B2B Sales28:21 - Why Training First Line Sales Managers Needs to be a Priority for B2B GTM Leaders42:29 - Why the Sales Enablement Movement Ultimately Failed in Improving B2B Sales Orgs51:21 - The Role of RevOps in Building a Sustainable Infrastructure for the Revenue OrganizationSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Any type of conversational analytics tool is the most powerful enablement tool that's out there right now, and people just need to use it.” - Tom Murtaugh“ Your sales manager is be going to become incredibly, even more important than they are today, because they're going to be the ones that even with a little bit of change, are going to have a lot of leverage over a lot of people.” - Tom MurtaughConnect with TomLinkedIn: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Nordic Capital Website: https://www.nordiccapital.com/ ShoutoutsAmanda Murtaugh: https://www.linkedin.com/in/amandabuck143/ Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ Philip CardiNeil Harrington: https://www.linkedin.com/in/neildharrington/  Scott Albro: https://www.linkedin.com/in/scottalbro/  Jeff Goree: https://www.linkedin.com/in/jeffgoree/ Andy Byrne: https://www.linkedin.com/in/byrneandy/ Michael Hargis: https://www.linkedin.com/in/mhargis/ Pablo Dominguez: https://www.linkedin.com/in/pabtexas/ Echo Valley on Apple TV+ Starring Sydney Sweeney & Julianne Moore (Only rated a 6.3/10 on IMDb)Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Chris Orlob, CEO of pclub.io and a B2B sales expert, dives into the pressing skills crisis facing sales teams today. He highlights the importance of mastering specific skills before moving on, advocating for a skill transformation loop in training. The conversation covers the shifting dynamics of B2B sales, emphasizing emotional intelligence and effective discovery techniques. With sales becoming increasingly competitive, Orlob stresses continuous learning as essential for success in this tech-driven landscape.

The old go-to-market playbook is broken, but in this episode we have a B2B SaaS founder who has actually figured out the new GTM playbook to grow in the current market.This SaaS savant is none other than the one and only David Boskovic, the CEO and Founder of Flatfile, which is the AI-powered data migration solution trusted by enterprise customers like ClickUp, HubSpot, Amazon, ADP, and Toast. David joins co-hosts Matt Amundson and Craig Rosenberg to outline how he and the GTM team at Flatfile developed their new AI-first go-to-market strategy, which is handling ten times the capacity of their previous GTM motions.David shares which of the 3 ways AI is being deployed works best, why you need to hire for individual contributors based on a candidate’s tastes, and why every Rev Ops team needs to hire an AI Engineer in order to stay ahead of the curve.Plus, David regales Matt and Craig with potentially the greatest story that’s ever been told on The Transaction, perhaps even better than ‘Maggots on a Plane.’Also, Craig threatens someone with having to wear a raccoon costume, Matt reveals the secret of what makes Craig great, and Sam the Producer experiments with some AI artwork.Critical TakeawaysWhen segmenting your ICP, segment into micro-verticals of 100–500 accounts, so you can then build tailored value propositions, demos, and collateral for each. AI allows this “luxury” level of personalization, which was once reserved for top accounts, to be applied to all targets. This dramatically improves first-call resonance, increases conversion rates, and differentiates your solution in competitive enterprise sales cycles.AI now allows you to turn things like costly enterprise-grade research into a commodity. Using tools like ChatGPT’s Deep Research or Perplexity you can produce insightful 40+ page market and account reports in hours instead of weeks. Validate quality by testing it with actual prospects. This “luxury” level of diligence, previously reserved for only top-tier accounts, can now be applied to every target at low cost.Having a CRM isn’t good enough. You should use AI to index every past customer/prospect interaction and extract key insights (budgets, pain points, workflows). Make this context instantly available to reps so every future conversation builds on a rich historical foundation.Every RevOps team, regardless of size, needs an AI Engineer to rapidly prototype and operationalize AI tools internally. If you want to remain ahead of the curve, you can’t be beholden to the slow development and innovation of tools from other SaaS companies.Operationalize everything in the company like a product. Treat your revenue org like a software system, debug bottlenecks, design orchestrations, and continuously iterate. The faster your GTM processes can be updated, the faster you can capitalize on new AI capabilities as they emerge.There are three main ways AI is deployed, Automation/Replacement, Augmentation, and Amplification. Amplification gives you the largest potential outcomes. To use the Amplification approach, deconstruct every GTM role into component tasks, give repetitive or low-value ones to AI, and keep humans focused on peaks of expertise like judgment, taste, and relationships.Chapters00:00 - Episode Preview01:32 - Introducing David Boskovic, The CEO & Founder of Flatfile02:49 - The Crazy, Raccoon-Filled Story Behind David Starting His First Company11:35 - Building an AI-First Go-To-Market Engine Internally from Scratch 15:07 - AI Lets You Do The ‘Unscalable’ At Scale with Quality and Affordability22:02 - Why Segmenting Prospects into Micro-Verticals Increases Your ABM Strategy’s Effectiveness33:26 - What it Takes to Spin Up an AI-First GTM Strategy & Why RevOps Teams Need an AI Engineer39:57 - Where is Software Going & Which of The 3 Ways to Implement AI Works Best47:12 - Why You Should Be Hiring Individual Contributors Based on Their Judgement51:34 - Sam Debuts Some Interesting AI Artwork of DavidSign up for our Newsletter: https://thetransaction.substack.com/Epic QuotesIt is incredibly hard to be optimistic enough about what’s possible” - David Boskovic“Dream your wildest dreams and see if you can make them happen. And if not, put them on the shelf, not for a year, but for a few weeks.” - David Boskovic“Part of what makes Craig great is his curiosity. He’s a lifetime learner.” - Matt AmundsonConnect with DavidLinkedIn: https://www.linkedin.com/in/dboskovic/ Website: https://flatfile.com/ ShoutoutsRory O'Driscoll: https://www.linkedin.com/in/roryodriscoll/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Endgame: https://www.endgame.io/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!