The Transaction

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!

80% of B2B buyers are already using AI in some part of their research process. Yes, you read that correctly, and we’ve got a special, repeat guest on the show to help you understand that shift in buyer behavior, how to capitalize on it, and much more.We are thrilled to welcome back AI and marketing expert Sydney Sloan, the Chief Market Officer of G2, to the program on this episode. Sydney joins Co-Hosts Matt Amundson and special Co-Host Scott Albro to explore how AI is being used by buyers when making purchasing decisions, the transition from SEO (Search Engine Optimization) to GEO (Generative Engine Optimization), and where business opportunities are emerging along the ‘AI Gradient.’ Plus, we get into some super tactical ways to improve your review strategy to increase trust and show up in AI search results.Also, Matt fawns over Cursor once again, Scott asks about tweeting at Founders, and Sam The Producer mercilessly throws Craig squarely under the proverbial bus.Critical Takeaways80% of buyers now use AI as part of their research process. In order to actually show up in results from an LLM, brands must embrace Generative Engine Optimization (GEO) by creating and optimizing brand content for people and problems, not just keywords.The best way to get more customer reviews is to embed review prompts in-app via tools like Medallia, Pendo, or Qualtrics. This leads to higher volume, verified reviews without incentives. Work with your product team to operationalize in-app review capture.To influence LLM outputs and improve buyer relevance, encourage customers to describe their specific use cases when writing reviews. This increases your company’s discoverability in AI-generated comparisons and rankings.Encourage founders and leaders to engage with reviews and even respond directly, this signals customer obsession and builds brand trust. Ps. you can pipe G2 reviews directly into Slack (Which is what Kyle Porter did at Salesloft).As AI agents become more integrated into your tech stack, you’ll start to feel the emerging need for an “AI architect” role in RevOps. This person would manage prompt engineering, agent workflows, and orchestration across sales, marketing, and customer systems.Chapters00:00 - Episode Preview00:48 - Introducing Sydney Sloan, Chief Market Officer at G204:15 - The Emerging Go-To-Market Playbook & New B2B Buyer Behavior Study11:25 - How to Use G2 to Rank Your Brand in ChatGPT Results for Best SaaS Tools 15:11 - What Makes G2 Reviews Stand Out & Why You Should Always Respond to Customer Reviews 18:46 - How Founder-Led Companies are Using Customer Reviews Creatively21:59 - How Buyers are Using AI Tools In Their Buyer Journey & To Compare Solutions26:47 - How Generative Engine Optimization Helps Your Brand Show Up in AI Search Results31:59 - Why Enterprises are Using AI Tools More Than Startups33:53 - The Meteoric Rise of Cursor & Which Categories or Niches are Ripe for AI Disruption44:24 - The AI Gradient & Why You Need an AI Architect on Your RevOps Team50:21 - Throwing Craig Under The Bus For Causing a Technical Issue & Wrapping UpSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“What we did six months ago is definitely not what we're going to do six months from now.” - Sydney Sloan“If you haven't yet started thinking about how do you show up in the LLMs, you're behind.” - Sydney Sloan“I don't think you can put all of AI generically into the hype cycle. I think you have to look at it by category or use case.” - Scott Albro“People use different language in LLMs than they do in search engines.” - Matt AmundsonConnect with Sydney SloanLinkedIn: https://www.linkedin.com/in/sydsloan/ G2 Website: https://www.g2.com/ G2.ai: https://ai.g2.com/ Putting AI Into Action Roadshow: https://sell.g2.com/ai-in-action-roadshow ShoutoutsKyle Porter: https://www.linkedin.com/in/kyleporter/ Kyle’s Episode of The Transaction: https://thetransaction.substack.com/p/startup-stunts-and-loving-your-customers Tim Sanders: https://www.linkedin.com/in/sanderssays/ Guillaume CabaneCursor: www.cursor.soQualified: www.qualified.comClay: www.clay.comHubSpot: www.hubspot.com1mind: www.1mind.comSalesloft: www.salesloft.comGong: www.gong.ioIron Mountain: www.ironmountain.comAirbnb: www.airbnb.comWaze: www.waze.comUber: www.uber.comLovable: www.lovable.so Windsurf: www.windsurf.ai Waymo: www.waymo.com Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Imagine you created a sales process so amazing that it was the only one customers actually enjoyed. Impossible? Today’s guest says no.Returning once again to grace this humble GTM-focused podcast with his immense intellect and immaculate presence is Brent Adamson, the co-author of The Challenger Sale and the upcoming new release, The Frame-Making Sale. Brent is back alongside Co-Hosts Matt Amundson and Craig Rosenberg to share how sellers can help B2B buyers become more confident in their own buying decisions, why “frame making” needs to be part of every seller's mindset, and how to tell powerful, emotionally engaging stories.Also, Craig confronts his own fleeting mortality, Matt says he likes “the big pullout”, and Sam the Producer contributes by swearing.Critical TakeawaysModern B2B buyers are overwhelmed and uncertain. Top-performing reps succeed by helping buyers build self-confidence in their decisions, not by pitching harder or throwing more whitepapers at them.The biggest predictor of successful SaaS deals isn’t objection handling, it’s whether the buyer believes they’re making a good decision. Sales teams should focus on guiding internal alignment and validating the decision process.Stop selling like you’re the expert and start selling like a guide. SaaS buyers want to see and hear what similar companies are doing when in their position. Social proof beats thought leadership when it comes to moving deals forward.Customer indecision is the real killer of your pipeline. B2B Buyers who feel overwhelmed delay action, your job is to make progress feel easy and safe.GTM leaders should train reps to speak with emotional clarity, using language that reflects how buyers feel, not just what they need to know.AI can’t replace human trust in B2B sales. Even as automation takes over task work, the real differentiator in SaaS GTM will be emotional connection and the ability to de-risk complex decisions.Vulnerability builds trust. Whether it’s storytelling, deal coaching, or just acknowledging awkward moments, honesty closes more than clever pitches.Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Episode Preview02:05 - Introducing Brent Adamson & Reliving the Maggots on a Plane Story06:40 - Brent Recounts a Near-Death Experience, Courtesy of United Airlines12:26 - The Origins of Brent’s Latest B2B Sales Research16:15 - Why B2B Buyers Want a Rep-Free Buying Process & The Importance of Human Connection in Selling19:35 - Customer Decision Confidence is the Biggest Factor in Driving High-Quality, Low Regret Deals26:50 - B2B Sellers Need to Help SaaS Buyers Learn How to Buy Solutions Intelligently31:26 - Sales Psychology will Play an Even Larger Role in B2B Moving Forward37:49 - SaaS Sales Reps Need to Become Buying Coaches for their Prospects41:18 - How to Increase Customers’ Confidence in Their Own Buying Decisions48:32 - The Key to Telling Compelling, Emotionally Engaging Stories53:25 - How Addressing the Elephant in the Room, like Bloody Eyeballs, can Create Better Human Connections  Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ When things like that make you nervous, uncomfortable, you don't run away from them you have to run right at 'em.” - Brent AdamsonConnect with Brent AdamsonLinkedIn: https://www.linkedin.com/in/brentadamson The Framemaking Sale: https://a.co/d/iQhqSzq Website: https://www.brentadamson.net/ A to B Insights Website: https://atobinsight.com/ ShoutoutsBrent’s Last Episode: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyerCoffee with Brent Adamson & Matt Heinz: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ 

Justin Michael, the founder of the Justin Michael Method and co-author of The Cold Call Algo, and Charles Needham, founding Account Executive at TitanX and co-author of the same book, challenge the notion that cold calling is dead. They discuss the importance of innovative approaches, such as using permission-based openers and AI tools for targeted outreach, to enhance engagement. The duo emphasizes adapting sales methods, mastering the art of conversation, and leveraging technology to strengthen relationships while keeping human interaction at the forefront.

In the second episode of 'The Direct Deposit,' Matt Amundson and Craig Rosenberg dive into the astonishing growth of Cursor, a startup providing an AI code editor for software developers, that has secured three funding rounds and achieved $500 million ARR in less than a year—all without a traditional marketing strategy. Matt & Craig explore how Cursor's product-led growth go-to-market model and simple SaaS pricing tiers contribute to their success in both raising new funding rounds and recurring revenue. Plus, there's a debate over the relevance of a traditional Go-To-Market team for such early-stage startups creating AI products. We also briefly touch upon Matt's favorite movie, John Carpenter's 'Big Trouble in Little China.'Join the newsletter to get new episodes straight to your inbox! Join here: https://thetransaction.substack.com/Enjoy this episode? Share it with a friend!Believe it or not, even in the tech-fueled world we live in, the number one way podcasts grow is word of mouth. So, if you learned something, lost your cool at something, or laughed at something from the show, give us a hand by sharing this with someone else who will get that same value from the show, regardless if it's education, entertainment, or outrage-inducing.

Join Jake Dunlap, CEO of Skaled Consulting and an AI B2B strategy expert, as he shares actionable insights on integrating AI into sales processes. Discover why sales leaders should move beyond mere activity metrics and emphasize critical thinking among their teams. Jake dives into the benefits of personalized outreach and AI tools, discussing how to craft tailored messages that resonate with clients. He also navigates the importance of training and the playful side of using AI to enhance client relationships—all while sprinkled with lighthearted anecdotes!

1. We are testing a new The Transaction product - The Direct Deposit. The idea is to take something that happened that week and one host asks the other host 5 questions. The result is a 5 minute quick hit.2. For this week's Direct Deposit, we cover RevFest. I'll give you the high level: 🐰 Jen Igartua and the Go Nimbly team killed it. Also, I am leading an unauthorized effort to rename it LoveFest 2026 but Matt Amundson keeps killing it. Lesss go! This is the first edition of The Direct Deposit presented by The Transaction.========================================Subscribe to the Newsletter: https://thetransaction.substack.com/ Follow the Show:- Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ - Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/- Sam's LinkedIn: https://www.linkedin.com/in/sam-guertin/ - The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ - The Transaction Website: https://thetransactionpod.com/ Ways to Tune In:- Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz - Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 - YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1 - More Options: https://thetransactionpod.com/subscribe

Scott Albro is back in The Transaction hot seat—and he’s not here to play nice. Scott brings a flame-thrower to traditional playbooks, urging GTM leaders to experiment wildly, think like founders, and stop chasing MQLs like it’s still 2014.Craig and Matt get Scott talking about everything from AI-driven storytelling to "vibe marketing," with detours through SDR history lessons, Red Bull stunts, and the existential crisis of printer ownership. If your go-to-market motion still depends on intent data and white papers… this episode might hurt (in a good way).Also, Craig breaks his keyboard, Matt mentions a little company he likes to call Red Bull, and Producer Sam desperately attempts to curry favor with Scott.Critical TakeawaysThe next wave of breakout companies will be driven by founders who embed themselves deeply into the Go-To-Market engine, not just product. Founder-led GTM creates authenticity, speed, and unmatched customer resonance.High-performing Go-To-Market teams in SaaS-land are shifting from one-size-fits-all playbooks to an experimentation mindset. It’s about making bold bets, measuring ruthlessly, and scaling what works, not chasing the hack of the week.Most so-called intent data is internet exhaust, not evidence of real purchase behavior.The best GTM orgs lead with narrative clarity, tying their solution to a broader shift in the world, anchoring it in customer pain, and delivering it with conviction. Skip this, and no one remembers you.Stunt marketing has a place in B2B SaaS. Think viral launches, bold storytelling, and emotional engagement. It’s not about gimmicks, it’s about being memorable in a world flooded with sameness.Chapters00:00 Episode Preview03:30 – The Go-To-Market Founder Concept07:00 – How Modern Go-To-Market Orgs Win13:00 – Growth Bets: What They Are and Why They Matter for B2B Marketers17:00 – Crafting a Resonant Story for your B2B brand21:00 – Aligning Product and Go-To-Market Motions (Finally)25:00 – Convincing B2B Startup CEOs to Experiment30:00 – Bland’s Viral Growth and the “Stunt Marketing” Debate36:00 – Storytelling Frameworks That Actually Work for Startups42:00 – Lethal Weapon Posters and Swarms of BeesEpic QuotesSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“If you're not reinventing your Go-To-Market org, you need to have a look in the mirror.” - Scott Albro“Founders can just do things that other people can't.” - Scott AlbroConnect with ScottLinkedIn: https://www.linkedin.com/in/scottalbro/ Shoutouts & Resources MentionedSkosh: https://www.merriam-webster.com/dictionary/skosh Skosh Usage over time: ​​https://books.google.com/ngrams/graph?content=skosh%2Csmidge%2Ctad%2Ciota%2Cmodicum%2Cwhit%2Cscruple%2Csmidgeon%2Cwee%2Cfathom&year_start=1800&year_end=2022&corpus=en&smoothing=3BlandMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ Tricia Gellman: https://www.linkedin.com/in/gellmansfmarketing/  Lena Waters: https://www.linkedin.com/in/lenawaters/Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

That’s right, no guest on this one, but not to worry, it’s just as insight-filled, yet off the rails, as all of our other episodes that you’ve come to know and love. Co-Hosts Matt Amundson and Craig Rosenberg discuss coming to terms with their go-to-market mid-life crises and how they have gotten up to speed on the latest AI advancements to help them get back in the game. Craig and Matt dig into how they’re using AI tools to create things like AI buyer personas, the impact B2B events are having, and what the new go to market playbook is beginning to look like.Also, Matt reveals his devious guilty pleasure and Craig shares how he lost his children in the desert.Critical TakeawaysInstead of prompting AI like a search engine, leaders should teach their teams to treat it like a colleague. Matt’s breakthrough came when he asked ChatGPT how to build personas and what information it needed to do so. By asking “how do I build X?” instead of “give me X,” teams unlock faster, higher-quality outcomes.Adopt a “Shock & Awe” mindset to break through. The market is saturated and fatigued—practical content alone isn’t enough. As Craig put it, GTM teams need to pair insight with surprise to break buyers’ patterns. Leaders should push teams to experiment with bolder formats, storytelling, or AI-powered personalization that “breaks the frame.”Account Research with AI is now table stakes for sales and marketing teams. Using AI for account research (before, during, and after sales calls) is no longer optional. Craig emphasized this is the new baseline expectation. If your team isn’t using tools like ChatGPT or Perplexity to prep on accounts and individuals before outreach, you’re behind.Before adopting any AI vendor solution, ask: “Can my team do this directly in ChatGPT or another general model?” As Craig noted, many startups at SaaStr were pitching account prep workflows that anyone can already do with a simple prompt.Chapters00:00 Episode Preview03:30 The GTM Midlife Crisis Hits – Why the old playbooks stopped working06:15 Building a New Playbook with AI in the Go-To-Market Hacker era08:45 Matt’s AI Buyer Persona Workflow – How to build and deploy AI agents for feedback13:15 Talk to Your AI Tools Like People 17:00 999/1000 Accuracy Rate – Why AI is now a mission-critical content editor25:30 Account Research is the New Minimum – How GTM teams are winning with better prep30:00  Matt & Craig just Want to Watch the World Burn37:00 Events Are Back, Baby – People crave new insights and in-person energy40:00 LinkedIn has changed, but it is still the social platform of choice for B2B brands45:00 Video Content: Raw vs. Polished – When it’s time to scale production (and when DIY still wins)50:00 Lost in the Desert: A GTM Parable – Craig’s real-life ATV crisis ends with a 10-year-old roasting himSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ It's the age of the Go-To-Market hacker.” - Craig Rosenberg“ Everybody needs to create a custom GPT. And if you want to know how to do it, just ask it. How do I create a custom GPT here?” - Matt AmundsonShoutoutsMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ Kristina McMillan: https://www.linkedin.com/in/kristinamcmillan/ David Boskovic: https://www.linkedin.com/in/dboskovic/ Jill Rowley: https://www.linkedin.com/in/jillrowley/ Jill Rowley’s tweet calling Craig’s Blackberry in 2012: https://x.com/jill_rowley/status/187231284970536960 SaaStrMark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ Copy.aiKlarity: https://www.klarity.ai/ Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Mandy Dhaliwal: https://www.linkedin.com/in/1mandydhaliwal/ Jake Dunlap: https://www.linkedin.com/in/jakedunlap/ James Kaikis: https://www.linkedin.com/in/jameskaikis/ Jordan Crawford: https://www.linkedin.com/in/jordancrawford/ Jordan’s Episode: https://open.substack.com/pub/thetransaction/p/inverting-your-go-to-market-strategy?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=falseLove the show? Give us a shoutout on LinkedIn and tell us what you loved!