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The Transaction

The Transaction

By: Craig Rosenberg & Matt Amundson | B2B Sales & Marketing Experts - Hosts of The Transaction
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 Welcome to The Transaction. The #1 Go-To-Market podcast on the planet. Hosts Craig Rosenberg and Matt Amundson, two legendary go-to-market leaders in their own right, talk weekly with the best sales, marketing, operations, and product leaders in the B2B SaaS world to understand what's working in the new playbook of the post-ZIRP market. But Craig, Matt, and their guests don't just talk theoretically, they share the stories and actionable tips, tactics, and strategies behind what's driving revenue growth that you can take and implement in your own go-to-market roles. Whether you're a Chief Revenue Officer leading a B2B SaaS sales and marketing organization, a marketing leader trying to drive bigger outcomes with your demand gen team, or a new sales rep, you'll learn and laugh every episode. From ABM to PLG, from MEDDIC to MEDDPICC, the world of business is constantly evolving. We’ll cover the who, what, where, when, why and most importantly how you get… The Transaction. About Your Hosts Craig Rosenberg is the Chief Platform Officer at Scale Venture Partners. He is a seasoned expert in B2B revenue growth, helping SaaS companies transition from founder-led growth to becoming high-growth Go-To-Market machines. Previously, Craig was a Distinguished VP Analyst at Gartner and co-founder of TOPO Inc., a research and advisory firm acquired by Gartner in 2020. Craig thinks Die Hard is a Christmas movie. Matt Amundson is the Chief Marketing Officer of DuploCloud. He is also an advisor for companies such as Sendoso and Salesloft. Prior to DuploCloud, Matt spent time as an Executive In Residence with Scale Venture Partners and led marketing departments at Census, Very Good Security, and Everstring, to name a few. Matt thinks Die Hard 2 is better than Die Hard. The Transaction is produced by Sam Guertin.The Transaction Economics
Episodes
  • The New AI-First Go-To-Market Playbook with David Boskovic, CEO & Founder of Flatfile - Ep 63

    The New AI-First Go-To-Market Playbook with David Boskovic, CEO & Founder of Flatfile - Ep 63
    Aug 18 2025
    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!
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    53 mins
  • How To Show up in ChatGPT Results & More B2B Marketing Secrets with Sydney Sloan, CMO of G2 - Ep 62

    How To Show up in ChatGPT Results & More B2B Marketing Secrets with Sydney Sloan, CMO of G2 - Ep 62
    Aug 8 2025
    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!
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    53 mins
  • Building B2B Buyers’ Self-Confidence & Selling WAY More with Brent Adamson - Ep 61

    Building B2B Buyers’ Self-Confidence & Selling WAY More with Brent Adamson - Ep 61
    Aug 1 2025

    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 Takeaways

    • Modern 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 Segment

    Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com


    Chapters

    00:00 - Episode Preview

    02:05 - Introducing Brent Adamson & Reliving the Maggots on a Plane Story

    06:40 - Brent Recounts a Near-Death Experience, Courtesy of United Airlines

    12:26 - The Origins of Brent’s Latest B2B Sales Research

    16:15 - Why B2B Buyers Want a Rep-Free Buying Process & The Importance of Human Connection in Selling

    19:35 - Customer Decision Confidence is the Biggest Factor in Driving High-Quality, Low Regret Deals

    26:50 - B2B Sellers Need to Help SaaS Buyers Learn How to Buy Solutions Intelligently

    31:26 - Sales Psychology will Play an Even Larger Role in B2B Moving Forward

    37:49 - SaaS Sales Reps Need to Become Buying Coaches for their Prospects

    41:18 - How to Increase Customers’ Confidence in Their Own Buying Decisions

    48:32 - The Key to Telling Compelling, Emotionally Engaging Stories

    53:25 - 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 Adamson


    Connect with Brent Adamson

    • LinkedIn: 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/


    Shoutouts

    • Brent’s Last Episode: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyer
    • Coffee with Brent Adamson & Matt Heinz: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/
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    57 mins
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