The Transaction

Rachel Dines is a B2B Marketing expert and advisor to multiple SaaS platforms, where she provides her specialty in deep tech companies with sales-led go-to-market motions. Rachel also writes a SubStack newsletter called Tech Dropout. Previously, Rachel was VP of Product and Technical Marketing at Chronosphere and a Forrester industry analyst turned product marketing leader. Rachel joins co-hosts Craig Rosenberg and Matt Amundson for a raucous romp through the world of building analyst relationships as a new SaaS vendor, the problem with startups having too many use cases, and why your B2B startup’s first marketing hire should really be a product marketer.Plus, Rachel reveals what happened when she gave a friend some less-than-amazing career advice.Also, Craig reveals his fondness for a certain slightly disparaging epithet, Matt releases his pent-up rage, and Producer Sam vows to make certain edits to the episode. Critical TakeawaysBuilding relationships with industry analysts at research firms, such as Gartner or Forrester, is only getting more important for B2B startups and scale ups. By the way, ‘building a relationship’ in this context is not code for just paying to play; we mean actually fostering real human connections with individual analysts, even before you think about paying a dime for a subscription for their firm.If you want your SaaS startup to show up in things like industry analyst reports and ‘magic quadrants’, start by finding and reviewing the evaluation criteria for those reports, which are publicly available. Bonus tip: try to get involved early when criteria are being set. For the ‘self scout’ of your product against the analyst’s criteria, bring in a few PMs (Product Managers) and SEs (Sales Engineers) to help you do a brutally honest self‑assessment, find weak spots, and see what shifts can be made. SEs are great resources to bring in because they are hyper aware of the critical issues with their own product and can provide clear-eyed insights.Pick one use case, one ICP (Ideal Customer Profile), and one persona to focus your go-to-market strategy on. Trying to be all things to all customers from day one is a recipe for dilution of your brand and burnout. Choosing one target (even if it feels narrow or imperfect) lets you focus your go-to-market resources, refine messaging, and build momentum for your company.Your first marketing hire should be a Product Marketer, not a demand gen specialist. Startups need someone who can define and refine messaging, narrative, positioning, not just pushing leads to sales. Without a clean story, demand gen spends often under‑deliver.With analysts, frequent light engagements, such as updates about new clients, features, saas founders turning over data, build familiarity and trust. Much of what shows up later in evaluations or quotes starts with these small, consistent touchpoints.Chapters00:00 - Episode Preview00:50 - Endearing Terms for The Wonderful People from Massachusetts03:27 - Introducing Rachel Dines, Author & Go-To-Market Advisor (Plus, Former Forrester Analyst)07:24 - A Quick Convo about Data Centers & The Mission Impossible Film Franchise10:24 - Giving Your First Solo Presentation as an Analyst with a Heads Up16:18 - Why Startups Need To Engage The Industry Analysts Early On20:22 - How Startups Should Approach Their Initial Analyst Relations Strategy29:35 - Matt Admits What Grinds His Gears31:23 - What Early Stage Startups Can do to Become Number One in the Magic Quadrant34:08 - Startups Should Start with One Segment, User, and Use Case46:51 - Why Your First Marketing Hire Should be a Product Marketer52:21 - Some not so great B2B Marketing career adviceJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“Focus, in the Go-To-Market side especially, is always the greatest Achilles heel of so many startups” - Rachel Dines“Pick a lane and win” - Matt Amundson“I can be bought for tiramisu” - Rachel DinesConnect with RachelLinkedIn: https://www.linkedin.com/in/rdines/ Substack: https://racheldines.substack.com/ Website: https://www.racheldines.com/ How I Hacked the Moon: https://a.co/d/eSYYRWG ShoutoutsScott Mersy: https://www.linkedin.com/in/smersy/ Sam McKenna: https://www.linkedin.com/in/samsalesli/ Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge Mission: Impossible - Rogue Nation (Christopher McQuarrie, 2015)The Studio (Apple TV+)Last Week in AWS (Newsletter): https://www.lastweekinaws.com/ Corey Quinn: https://www.linkedin.com/in/coquinn/ CursorWindsurfLovableChris Degnan: https://www.linkedin.com/in/chris-degnan-524470/ SnowflakeDenise Persson: https://www.linkedin.com/in/denisepersson/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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!

B2B sellers and sales leaders find themselves in the midst of an unprecedented Go-To-Market skills crisis at a time when budgets are shrinking and selling is getting harder.Joining the show once again is the inimitable Chris Orlob, CEO at pclub.io, the #1 Skill Transformation Platform for Revenue Teams. Chris joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into where the current sales skills crisis came from, what sales leaders can do to help improve their sales reps’ skill capacity, and why sales reps should start with getting a concrete understanding of a proper discovery process.Plus, Chris discusses why B2B sales leaders should implement a skill transformation loop into how they train their sales teams.Also, Craig addresses an elephant in the room, Matt bemoans the illegality of ‘hacking darts’ in Foster City, and Sam the Producer laughs at Craig.Critical TakeawaysInvesting only in Sales Process is not enough to help sellers hit their targets, because process only covers what to do. Whereas, Skill capacity doesn't stop at what to do. Skill capacity is what to do, why to do it, and how to do it so that you're building judgment. This way, reps can have audible-ready, rich business conversations that create value for both buyers and customers.When training sales reps on new skills, it’s best to make sure they master one skill before they move on to learning another. This builds skill depth, rather than very shallow skill breadth. Without ensuring competency in one skill before moving on, all you achieve is motion without accomplishment.The first, foundational skill that reps should train on is sales discovery. Having a strong grasp on discovery will help sales reps build stronger additional skillsets. It’s harder to build the other sales skills without having a solid understanding of sales discovery.As companies’ go-to-market motions become increasingly complex, if they don’t address the low skill capacity of their sales team, they incur a growing ‘skill deficit’, which if left unchecked will lead to catastrophic results down the line.Chapters00:00 - Episode Preview02:21 - Introducing Chris Orlob, CEO of pclub.io03:33 - An Instructive B2B Sales Story: How to Interact with Procurement Leaders08:06 - Craig & The Case of The Bloody-Eyed Business Meeting12:19 - The State of the B2B Sales Skills Crisis in Go-To-Market Today25:40 - Discovery is the Fundamental Sales Skills Reps Need to Learn33:24 - How B2B Companies Should be Approaching Discovery and the Buying Process in Today's Market44:25 - Why B2B Sales Leaders Need to Implement a Skill Transformation Loop Into Their Teams' TrainingJoin our Newsletter: https://thetransaction.substack.com/Epic Quotes“We are in an era of a Go-To-Market skills crisis.” - Chris Orlob“Reps and sellers are drowning in technology, but starving for skills and skill capacity.” - Chris Orlob“AI is not the solution to the skill gap.” - Craig Rosenberg“If they can't build a case for me of how they're going to solve my problem, I don't really want to buy it.” - Matt AmundsonConnect with ChrisLinkedIn: https://www.linkedin.com/in/chrisorlob/ pclub.io Website: https://www.pclub.io/Twitter: https://twitter.com/Chris_Orlob ShoutoutsChris’s Last Episode on The Transaction: https://thetransactionpod.com/episodes/to-gate-or-not-to-gate-content-with-chris-orlob-the-transaction-ep-005 Scott Albro: https://www.linkedin.com/in/scottalbro/  Paul Rosenberg: https://www.linkedin.com/in/paul-rosenberg-0970421/ Ryan Tibbetts: https://www.linkedin.com/in/ryantibbetts/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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/ 

What if cold calling isn’t dead—but everything we know about it is?From dissecting permission-based openers to dunking on dated tactics, sales experts Justin Michael and Charles Needham make a bold case for why the phone isn’t dead as a sales channel—it’s just misused. Justin Michael, aka the John Wick of executive coaching, is a longtime B2B seller and sales trainer, as well as the Founder of the Justin Michael Method and co-author of The Cold Call Algo. Along with being Justin’s Co-Author on Cold Call Algo, Charles Needham is a bona fide B2B Sales Badass in his own right, being the Founding Account Executive at TitanX and the Founder of Needham Advisory Group. Joining co-host Matt Amundson for this episode, Charles and Justin dig into the unique benefits of cold calling, the evolving role of Sales Development Reps, and where sales orgs should be trying to implement AI sales tools.Critical TakeawaysEncouraging SDRs to see cold calling as a means for intelligence gathering rather than merely scheduling meetings can lead to better insights and long-term relationships.The traditional methods of cold calling, like repetitive sales scripts, are losing effectiveness. Incorporate permission-based openers and insightful questions early in the call to create curiosity and engagement. Leveraging AI to clean and target data can dramatically increase the effectiveness of your outreach strategy. By focusing only on prospects who are likely to answer, teams can improve their connect rates and overall outcomes.Train teams to focus on tonality and pacing during calls. Using neutral, calm tones, can help in calming down the prospect's initial resistance and opening up a more natural conversation.Chapters00:00 Intro01:09 Introducing Justin Michael and Charles Needham02:55 Discussing B2B Sales Strategies and Cold Calling as an effective sales channel03:37 Justin's B2B Sales Stories and Experiences08:07 Charles on Modern Sales Challenges for SaaS Startups13:22 The Emerging Role of AI in B2B Sales Today17:10 Cold Calling Sales Techniques and Best Practices30:29 Debating Cold Call Openers32:53 Unified Theory of Cold Calling for B2B sales39:03 Mastering Tonality and Rhythm during B2B Sales Calls56:26 The Future of Cold CallingSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Cold calling is a mechanism to survey the market and have conversations, rather than going in there like 8 Mile Eminem style—one shot, one opportunity to book a meeting.” - Charles Needham“Problems are isolating by nature. So if you can show someone that it’s common, they’ll open up more.” - Charles Needham“ People buy emotionally, they justify with logic.” - Justin MichaelConnect with Justin MichaelLinkedIn: https://www.linkedin.com/in/michaeljustin/ Website: https://www.salesborgs.ai/ Get the Book: https://coldcallalgo.com/ Connect with Charles NeedhamLinkedIn: https://www.linkedin.com/in/charles-needham/ TitanX Website: https://www.titanx.io/ ShoutoutsKai-Fu Lee: https://www.linkedin.com/in/kaifulee/ AI Superpowers: China, Silicon Valley, and the New World Order by Kai-Fu Lee: https://a.co/d/ex6F2Yz David Dulany: https://www.linkedin.com/in/davidkdulany/ Wyzer.aiMike Bosworth: https://www.linkedin.com/in/mikebosworth/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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.

Everyone's talking about how amazing AI can be, but there’s a real dearth of actionable advice on how to actually put generative AI to work for your sales, marketing, customer service, or other go-to-market team. Well, that was until we talked to this week’s incredible guest…Jake Dunlap is truly a thought leader on using AI in B2B go-to-market strategies and is the CEO of Skaled Consulting, a revenue performance agency dedicated to helping B2B companies scale smarter. Jake joins Matt Amundson and Craig Rosenberg to delve into the tactical and practical ways he is implementing AI tools into go-to-market motions and how you can get the benefits of new AI technology. Jake and Matt have both been building some interesting agents and custom GPTs, and they get into how they set them up and how they are using them. Jake discusses why B2B sales leaders need to stop managing by measuring sales rep activity, how to avoid major pitfalls when implementing generative AI tools in your organization, and how to build an efficient and effective outbound strategy today. Also, Craig shares that both of his cars were stolen straight out of his driveway, Matt remembers the name of a consumer product, and Producer Sam interrupts to ask a question about podcasts.Critical TakeawaysTrain your sellers to think critically. Don't just provide templates. Teach your sales team how to analyze trends, customize outreach, and add value based on their understanding of the buyer's industry and challenges. Encourage creativity and problem-solving skills.Measure outcomes, not just the activities of your sellers. Shift your focus from tracking the sheer volume of sales activities to measuring meaningful conversations and outcomes. The quality of interactions should take precedence over the quantity.Start using AI to improve bottlenecks that you or your team are facing. While there are myriad amazing things you could do with AI, by focusing on the boring, unsexy things that constrain your revenue team, you’ll actually drive greater outcomes for your team.Sellers, try doing the type of outreach that isn’t massively scalable, but that provides immense value and really sticks out. This is likely going to yield better results than hitting ‘send all’ again. For example, you could use new AI tools like Deep Research and NotebookLM to create customized podcasts and white papers tailored to the specific role and industry needs of a contact at a target account.AI is not a go-to-market strategy in and of itself, nor is it something that can be applied in a blanket fashion across every role or function. Let sellers play to their strengths. For example, some reps are great on video, while others excel on the phone. Don’t force every sales rep into the same volume-driven mold. Focus on outcomes, not activities.Don’t wait for Enablement to hold your hand and train you on using AI. As Jake said, “ sales leaders, executives, listen to me. You have to learn this yourself. You cannot outsource this through rev ops.” Why is that? Because AI is more than just another tech tool, it’s a fundamental shift in problem-solving. Don’t sit around waiting for a playbook—experiment, build, and iterate. Training wheels are for losers… and small children.Chapters00:00 - Episode Preview00:36 - The Fast & The Furious: Silicon Valley Drift07:39 - Two Insightful Examples of How B2B Companies are Using & Operationalizing Gen AI11:41 - Why B2B Sales Reps Need to Start Using AI for Account Research & How to Get Started with New AI Tools 13:36 - How to Build AI Agents for Each Buyer Persona & How Matt is Using AI as a Chief Marketing Officer16:08 - The Power of Building Custom AI Agents for Revenue Growth22:22 - B2B Sales Leaders are Still Getting Stuck on Activity Metrics, When They Should Measure Impact30:04 - How to Construct a Successful B2B Outbound Strategy in the Current Market37:01 - How Will Anthropic and OpenAI’s Custom GPTs Integrate with Existing SaaS Tools & Will Gen AI Tools Replace the Go-To-Market Function as We Know It?42:01 - What Hurdles to Avoid When Implementing AI Tools in Your Company & Why Leaders Need to Stay on Top of AI AdvancementsSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Stop asking the question, ‘What’s our AI go-to-market strategy?’ It’s not the right question.” - Jake Dunlap“The goal are the outcomes, not the activities.” - Jake Dunlap“Outbound never ends. You cannot take a project-based mindset to outbound.”  - Jake DunlapConnect with Jake DunlapLinkedIn: https://www.linkedin.com/in/jakedunlap/ Website: https://skaled.com/ The Innovative Seller (Jake’s Book): https://www.jakedunlap.com/the-innovative-seller ShoutoutsDirty Mike and The Boys: https://youtu.be/1FkK8ZFE7Y0?si=WpJ9miacA2CdLq0u NotebookLM: https://notebooklm.google/ The Goal: A Process of Ongoing Improvement by Eliyahu M. Goldratt & Jeff Cox: https://a.co/d/03F3RE2 Matt Heinz: https://www.linkedin.com/in/mattheinz/ Matt’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/how-to-implement-ai-in-your-go-to?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Sydney’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false The Club: https://store.winner-intl.com/the-original-club-p2.aspx Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

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!

B2B marketers keep making the same mistakes when it comes to events, only to end up asking why they didn’t see any ROI. Thankfully, we knew just the right person to help you improve your field marketing game…Amy Holtzman is the Chief Marketing Officer of CHEQ, the leader in go-to-market security, and one of the best B2B marketing leaders in SaaS, especially when it comes to creating unforgettable experiences. Amy joins co-hosts Craig Rosenberg and Matt Amundson to explore how to plan an event marketing strategy that doesn’t suck, why you need to think beyond the vendor booth at a conference to see real ROI, and even how traditional paid search is holding up amidst the onslaught of AI advancements. Also, Craig says something he immediately regrets, Matt makes an unsettling insinuation, and Producer Sam calls someone a naughty word.Critical TakeawaysEvents are still alive, if you are willing to put in the work to make them stand out. You can’t just “show up and hope.” Great booths need real strategy, creative hooks, and a human-first approach that makes people actually want to engage.Whether selling B2B or B2C, even strong demand dies in broken systems. Want revenue? Get your backend in order first so you can deliver remarkably good customer experiencesProspects are already using ChatGPT to build vendor shortlists. If your GTM doesn’t account for AI-powered discovery, you’re already behind.Despite the hype around AI, traditional paid search drove record enterprise deals for CHEQ in Q1 of this year, especially long-tail keywords. Don’t ditch the old toolbox just yet.Chapters00:00 - Episode Teaser00:34 - Amy’s Amazing Hat, Chain Restaurant Pub Crawls, & the Apollo Theater10:36 - Introducing Amy Holtzman, Chief Marketing Officer at CHEQ13:46 - Lessons to Learn from the Worst Sales Experience Ever25:53 - Search is Still Driving A Surprising Amount of Enterprise Deals30:50 - Breaking Down the New G2 Research on B2B Buying Behavior & How AI is Impacting Vendor Shortlists35:08 - How to Get More ROI from your Event Strategy & Field Marketing Mistakes to Avoid39:46 - Sponsoring Niche Events can Pack a Massive Punch for Smaller B2B Brands44:44 - Thinking Beyond the Booth When Planning out Your Event StrategySign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Really strong quality work and great execution never goes out of style, no matter what the trend is and what's working.” - Amy Holtzman“If you want to sell things, make sure you have enough salespeople.” - Amy Holtzman“I rub the thing” - Craig RosenbergConnect with AmyLinkedIn: https://www.linkedin.com/in/aholtzman/ Website: https://cheq.ai/ ShoutoutsEvery Little Step I Take by Bobby Brown: https://youtu.be/P0FKzPfsxA4?si=o3k9Iepu3KwnP1Aa Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Jessica Lin: https://www.linkedin.com/in/jessicalin8/ Amy’s Episode on The Drafting Table: https://www.thedraftingtablepodcast.com/content/conferences-arent-a-vibe-theyre-a-sales-channel-how-to-actually-make-them-worth-it-with-amy-holtzman-cmo-at-cheq Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ G2 Buying Behavior Report: https://learn.g2.com/2025-g2-buyer-behavior-reportSydney Sloan: https://www.linkedin.com/in/sydsloan/ Scott Albro: https://www.linkedin.com/in/scottalbro/ The Tonga Room: https://www.fairmont-san-francisco.com/dine/tonga-room-hurricane-bar/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

AI use cases & tactics are moving at a million miles per hour which can make it hard to adopt some of these amazing innovations into your go-to-market strategy. Thankfully, we knew just the guy to have on the show to help us put into practice what otherwise could seem like technological mumbo, and or jumbo.That man’s name is Jordan Crawford, the Founder of Blueprint GTM and one of the foremost go-to-market engineers innovating B2B sales and marketing on the cutting edge of AI advancements.Jordan joins co-hosts Craig Rosenberg and Matt Amundson to dive into where we’re thinking about our go-to-market strategy and tech stack in the wrong way, how to segment cold outbound leads in an effective, yet scalable way based on pain, and how to evolve your revenue organization to excel in the new, ai-powered world.Also, Craig shows off his sandwich shop shirt, Matt gets on yet another soapbox, and Producer Sam is asked for his opinion.Critical TakeawaysIdentify specific, narrow segments by understanding unique heuristics that indicate a need for your product. For instance, identifying complex sales teams with high traffic who would benefit from LeanData's routing solutions is more effective than broad targeting.You need to understand your customers and their pain before bringing in tools like Clay or ZoomInfo. Sales leaders should spend time with SDRs to gain insights on what truly resonates with prospects, ensuring that any data or tools used are enhancing proven strategies rather than replacing deep understanding.The burden placed on SDRs to make sense of complex data without adequate support is a recurring issue. Leaders should simplify data insights and ensure SDRs are equipped with actionable, digestible information, alleviating stress and improving effectiveness. Adopt a 'pain-qualified' segmentation approach. Identify segments that not only fit demographic profiles but also exhibit specific pain points that your product can address, such as complex routing needs in high-traffic sales teams for LeanData. This ensures messages are highly relevant and more likely to result in conversions.Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 Introduction: The Intimidating Box01:07 Mr. Pickles and Misadventures in Pocket Dialing04:42 Craig’s Midlife Go-To-Market Crisis05:31 What’s broken with the Old Go-To-Market Playbooks07:30 What is The New World of Sales and AI13:04 Segmenting and Targeting with Data16:43 Permissionless Value Prop in Action23:25 The List is the Message25:47 Methodology and AI Integration26:55 Understanding Customer Segments29:56 Challenges in Sales and Marketing33:18 Effective Campaign Strategies35:16 Adapting to AI and Market Changes38:37 Purpose of Niche Targeting and SuccessSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“The list is the message.” - Jordan Crawford“Never in my life has there been a more intimidating box than the ChatGPT, Claude, Gemini entry box because for the first time in our lifetimes, and maybe human history, we are the limiters.” - Jordan CrawfordNew TermsPain Qualified Segment: Two to five unique heuristics, often that imply tension.Connect with JordanLinkedIn: https://www.linkedin.com/in/jordancrawford/ Website: https://blueprintgtm.com/ YouTube: https://www.youtube.com/@BlueprintGTM Jordan’s Latest Course: https://pvp.blueprintgtm.com/subscribe ShoutoutsScott Albro: https://www.linkedin.com/in/scottalbro/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved! 

Matt Heinz, the President of Heinz Marketing, is a top 50 Sales & Marketing Influencer and a prolific thought leader in the B2B marketing space. Matt digs into why B2B marketers should invest more in brand as the AI Age progresses, whether the Chief Marketing Officer should report to the Chief Revenue Officer, and why B2B marketers are so terrible at naming products and concepts.Also, Craig ponders the meaning of parabolas, Matt ranks the best men’s hair in B2B Marketing, and Producer Sam gets confused by Craig talking about bats.Critical TakeawaysDevelop a structured approach to AI adoption in Go-To-Market strategies. Instead of engaging in 'random acts of AI,' organizations should create an accountability chart detailing which jobs are better suited for machines and which require human intervention. Personal connections and credibility can differentiate a brand in a noisy market. Efforts should be made to maintain and build these relationships alongside leveraging scalable technology.While marketing attribution is important, it should not solely focus on credit for past actions. It should be used to create a more predictable and reliable path towards future outcomes. Go to market teams need to look at attribution as a tool for driving the right behaviors and actions, rather than merely analyzing past performance.Signals, including “intent signals”, need to be understood in context and not treated as immediate leads. Revenue teams should use signals to inform their understanding of where a prospect is in the buying journey, rather than assuming all signals indicate readiness to buy. This nuanced understanding can improve targeting and engagement efforts.Even as AI and automation take on more tasks, creativity and strategic thinking remain irreplaceable. Teams should focus on leveraging AI for efficiency while reserving creative and complex problem-solving tasks for human talent. This balance can drive innovation and maintain a competitive edge.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 Episode preview00:30 Craig Goes Batty and Some Auction Antics04:13 Introducing Matt Heinz, President of Heinz Marketing08:07 B2B Marketers are Terrible at Naming Concepts, Products, and Strategies19:16 Should CMOs Report Up to CROs in B2B SaaS?22:03 Ranking the Best Hair Amongst Men in B2B & Matt Confesses to Rocking a Mullet27:27 How Go-To-Market Teams are Using AI & Evolving Their GTM Strategy with AI37:13 Trust & Personal Relationships are Differentiators in the Age of AI Marketing Tools42:11 The Role of Data & The Cloud Data Warehouse in B2B MarketingSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ We shouldn't be guessing anymore, we should be using the agents to tell us how to improve right away” - Matt Heinz“ If I have more noise and less time, who am I going to prioritize? It's the people I enjoy. It's the people I trust. It's the people I like. That's going to be a huge differentiator moving forward.” - Matt Heinz“ I don't want anybody to think that I'm not down with intent signals. I'm down with signals because right now the hardest thing in the world to do is engage.” - Craig Rosenberg“If you are looking for the solution in the tool, you're bound to fail.” - Matt AmundsonConnect with Matt HeinzLinkedIn: https://www.linkedin.com/in/mattheinz/ Website: https://www.heinzmarketing.com/ ShoutoutsBat Tours in Austin: https://www.austintexas.org/things-to-do/outdoors/bat-watching/ Bert Kreischer’s Raffle Story: https://youtu.be/EsCadHpBdkY?si=GDRoQpWQ9B1Z_55l Coffee with Brent & Matt: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ Joe Chernov: https://www.linkedin.com/in/jchernov/ Steve Woods: Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in Lars Nilsson: https://www.linkedin.com/in/lanilsson/ Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales Ted Purcell: https://www.linkedin.com/in/tedpurcell/ Adam Robinson: https://www.linkedin.com/in/adam-robinson-4b156810/ Adam’s Episode: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal Anthony Kennada: https://www.linkedin.com/in/akennada/ Chris Walker: https://www.linkedin.com/in/chriswalker171/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Mary Meeker: https://www.linkedin.com/in/mary-meeker-5823ba48/ Simbe RoboticsMperativBrent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Not a long time ago in a Silicon Valley not too far away, the sales infrastructure of almost every startup was an immature, undisciplined mess… Until a certain former printer salesman turned up in town…Lars Nilsson is the Founder and CEO of SalesSource, but you probably know him from his legendary run as the VP of Global Sales Development at Snowflake. To Craig, Lars is, “one of the masters of the universe in sales development and inside sales and business, and clearly very fit.” Lars joins co-hosts Craig Rosenberg and Matt Amundson to discuss how we got to the current state of sales training and enablement in B2B SaaS, why the GTM Engineer role is the next hire you need to make to improve your revenue team, and whether having B2B sales reps roleplay with AI avatars is the way forward or just a waste of time.Also, Craig relives stories of his past mastication, Producer Sam fights yet another losing battle, and Matt warns everyone that, “ we're going to go deep. We're going deep.”Critical TakeawaysRecognize and elevate the Sales Development Representative (SDR) function within the organization. CEOs and senior leaders should regularly acknowledge the impact SDRs have on pipeline generation. Simple acts of recognition can significantly boost team morale and performance.Create a systematic process to gather and disseminate insights and customer feedback from the front lines of sales. SDRs interact with numerous prospects daily, and their feedback can inform product development, marketing strategies, and sales tactics. Ensuring this information reaches executive levels can align the organization’s initiatives more closely with market needs.Giving your sales team more ‘at-bats’ to practice and hone their craft results in better sellers. Leverage AI-based tools like role-playing bots to enhance SDR training. These tools can provide a scalable, less intimidating way for SDRs to practice their pitches and objection handling. Encourage cross-departmental learning within your org. Facilitate opportunities for SDRs to learn from other teams, such as marketing, operations, and customer success. This cross-training can develop well-rounded employees and ensure smoother transitions when SDRs move into new roles within the company.Consistently produce and share content that showcases successful customer stories and product use cases. Having a dedicated resource person, like the retired beat reporter who worked with Lean Data, can ensure continuous content production that drives engagement and educates prospects.Encourage a culture where continuous learning and improvement are part of daily operations. Regularly update training programs and technology stacks, and stay abreast of the latest trends and tools in sales and marketing to maintain competitiveness.Sponsored Segment~Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Episode Preview00:35 - Craig Eats like Cookie Monster03:13 - Introducing Lars Nilsson, the Founder & CEO of SalesSource and Former VP of Global Sales Development at Snowflake07:46 - The Genesis of Sales Development in SaaS & How it Expanded on Account-Based Marketing Concepts13:23 - How Xerox Trained Their B2B Sales Team and What Startups Should Learn from Their Success21:34 - The Emerging GTM Engineer Role & The Impact Its Having on B2B Sales Teams Using AI Tools34:59 - Should B2B Startups Try to Replicate the SDR Academy from Snowflake38:17 - How Startup Leaders Can Elevate the SDR Role & Why They Must Show Their Appreciation for this Critical Function45:42 - The Importance of AI Roleplaying Tools for Training B2B Salespeople54:11 - Startups Founders Should Play a More Active Role in Developing Their Go To Market StrategySign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ I just think that Snowflake with 300 SDRs today, maybe in two years, they'll have 50. But each one will be able to punch above, like they are five individuals because of all the automation.” - Lars Nilsson“ One Go-To-Market engineer today is going to make five SDRs punch like they're 25.” - Lars NilssonConnect with LarsLinkedIn: https://www.linkedin.com/in/lanilsson/ SalesSource Website: https://salessource.com/ ShoutoutsStuart Silverman: https://www.linkedin.com/in/stuart-silverman-32132/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Karan Singh: https://www.linkedin.com/in/karan-singh-29269015/ Travis Henry: https://www.linkedin.com/in/travisjhenry/ Brendan Short: https://www.linkedin.com/in/brendan-short/ Pete Kazanjy: https://www.linkedin.com/in/kazanjy/ Jason Vargas: https://www.linkedin.com/in/jasonvargas/ John Barrows: https://www.linkedin.com/in/johnbarrows/ Becc Holland: https://www.linkedin.com/in/beccholland-flipthescript/ Hyperbound: https://www.hyperbound.ai/ Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ Morgan Ingram: https://www.linkedin.com/in/morganjingramamp/ Kevin Dorsey: https://www.linkedin.com/in/kddorsey3/ Trish Bertuzzi: https://www.linkedin.com/in/trishbertuzzi/ Scott Barker trying to book a meeting with Avarra’s AI Avatar Role Play: https://youtu.be/90EQSxcIhqc?si=gKDiVmsnadrsk_IY Tavus: https://www.tavus.io/ 

Most B2B brands (yes, probably yours) think that they’re ‘customer-centric’, and yet none of them ever stop droning on and on about their product and its ‘revolutionary’ features.Lauren Goldstein is the Chief Growth Officer of Winning by Design and Co-Founder, Board Member, Chair of the Board of Directors for Women in Revenue. Lauren joins co-hosts Craig Rosenberg and Matt Amundson to chat how B2B sellers and marketers can connect with buyers in the way buyers want them to, why having a diverse leadership team is an invaluable asset for any startup, and why “Strategic RevOps” is enabling breakthrough growth for SaaS startups.Also, Craig shocks the world by caping for his portfolio companies’ sales pitches, and Matt mentions the production design aesthetic of a niche director.Critical TakeawaysImplement structured mentorship programs in your org where experienced team members can guide less experienced colleagues, as this can lead to increased job satisfaction and retention, on top of the personal and professional development of your whole team.Instead of spending time on a sales call waxing poetic about the ‘revolutionary’ features of your product, use that time to ask your prospect what success looks like for them. How are they measured as a success or failure? Uncover that ideal state and help them understand how your product can get them there, provided it actually can; otherwise, don’t waste their time and yours.Consider using ‘Reverse Demos’, where instead of showing off your product right away, you have the customer outline their current processes and challenges. While this approach might not work with all types of buyers, it could be effective in understanding complex systems and better tailoring your pitch to the customer's actual needs.Cross-functional alignment across your go-to-market team is crucial. Sales, marketing, product, and finance teams need to work collaboratively, understanding each other’s objectives and challenges. Regular inter-department meetings to align goals and strategies help everyone move in the same direction towards shared business goals.Companies that have strategic RevOps roles are better at aligning their sales and marketing efforts with financial and operational goals, ultimately driving growth and operational efficiency.Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Episode Preview00:30 - Are the Angels a Real Team & Breaking Down the Backgrounds03:24 - Introducing Lauren Goldstein, Chief Growth Officer of Winning By Design & Co-Founder of Women in Revenue06:36 - The Origin Story of Women in Revenue (The group, not the concept)18:17 - The Immutable Impact Diverse Teams in Business23:43 - B2B Tech Brands Are NOT Connecting Buyers in the Ways That SaaS Buyers Want31:39 - What is a ‘Reverse Demo’ & Why is Gartner Analyst Dan Gottlieb Recommending it36:00 - Revenue Growth in SaaS Comes Back to Identifying the Right Buyers40:43 - The Critical Role of Rev Ops in B2B Go-to-Market Strategy for SaaS44:00 - Strategic Rev Ops: The Key to Integration & Go-To-Market AlignmentSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Managing multiple stakeholders in an enterprise sale is not a new thing. But it's more than managing multiple stakeholders, it's really about helping to facilitate a conversation where they're all understanding the problem in the same way and can connect back to a common denominator.” - Lauren Goldstein“ There is no greater liar as a buyer, than a marketer.” - Matt Amundson (A Marketer)Connect with LaurenLinkedIn: https://www.linkedin.com/in/laurengoldstein/ Winning by Design Website: https://winningbydesign.com/ Women in Revenue Website: https://womeninrevenue.org/ ShoutoutsSydney Sloan: https://www.linkedin.com/in/sydsloan/ Sydney’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with Katharine Reagan: https://www.linkedin.com/in/katharine-reagan/ Shari Johnston: https://www.linkedin.com/in/sharijohnston/ Jen Dimas: https://www.linkedin.com/in/jenpd/ Tracy Eiler: https://www.linkedin.com/in/tracyeiler/ Jim Walker: https://www.linkedin.com/in/jwwalker/ Robert Koehler: https://www.linkedin.com/in/rkoehler/ RadiusMarketoMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ InsideViewBabcock JenkinsDan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan’s Episode: ​​https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb MiroMark Kosoglow: https://www.linkedin.com/in/mkosoglow/ Mark’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity Kelly DeHart: https://www.linkedin.com/in/kelly-dehart-18b63315/ Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Colin Gerber: https://www.linkedin.com/in/colinsgerber/ SocureAdam B. Needles: https://www.linkedin.com/in/abneedles/ Adam’s Episode: https://open.substack.com/pub/thetransaction/p/the-new-go-to-market-blueprint-with AnnuitasLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

Ana Leyva advises early-stage startups at Pear VC on their go-to-market strategy to help them build stunning sales motions that set them up to scale. Ana provides pre-seed and seed startups with her first-hand experience as a seasoned operator with past roles at tech unicorns Box, ServiceTitan, and Vanta. Ana joins Co-Hosts Craig Rosenberg and Matt Amundson to delve into how to transition beyond a founder-led sales motion without losing their special perspective, why insight-driven outreach beats crappy sales personalization in B2B, and the two foundational pillars that you need to have in place to build a strong go-to-market strategy.Additionally, Ana details the importance for founders to be extremely disciplined with their Ideal Customer Profile and who they allow to steer the course of the future of their company.Also, Craig gets a ton of text notifications, and Matt muses about buying Craig a present for Easter.Critical TakeawaysThe crappy bit of personalization you grabbed from LinkedIn and added to your stale cold outbound email is not going to set you apart. ‘We went to the same school’ doesn’t help that decision maker develop a solution to the problems they’re facing.Rather than relying on bare-minimum ‘personalization’, put your thinking cap on and reach out with a business insight that can actually help your prospect learn more about their business, understand their problem better, or make a more informed decision.As hard as it can seem to turn down customers early on, founders need the discipline to focus on prospects who will truly benefit from their product, and saying no to the wrong fit is crucial for building long-term customer relationships.The bedrock of your go to market strategy should be built upon endless customer obsession and very strict ICP (Ideal Customer Profile) parameters. That ensures you deeply understand the pain your customer solves and can build a product to solve that pain effectively. Don’t just let your customers come to you, you need to pick the right protagonists for the epic narrative that you are creating for yourself and your customers. Be picky about who you allow to join and steer the arc of this grand story you are embarking on. Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Episode Preview00:20 - Squishy Pineapples & The 1995 UCLA Bruins04:01 - Introducing Ana Leyva, GTM Leader at Pear VC08:29 Selling at B2B Conferences on the Road as a New Mom 11:32 - Focus on Providing Value, not on Bland “Personalization”21:33 - B2B SaaS Founders Need to Rewrite New Go To Market Playbooks27:24 - Scaling Your Sales Team & Shifting from Founder-led Sales34:53 - Discipline is a Founder’s Best Friend & Going Narrow is the Way to Win as a Startup45:06 - Is Cold-Calling Coming back in Style for SaaS Sales Teams?Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“I am sick of personalized emails.” - Ana Leyva“I always tell our founders, you’re not selling for the initial close; you’re selling for the renewal.” - Ana LeyvaConnect with AnaLinkedIn: https://www.linkedin.com/in/analeyva/ Pear VC Website: https://pear.vc/ ShoutoutsAJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ Brandon Redlinger: https://www.linkedin.com/in/brandonredlinger/ Brent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’s Episode: Jen Allen-Knuth: https://www.linkedin.com/in/demandjen1/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Jason’s Post on LinkedIn: https://www.linkedin.com/posts/jasonmlemkin_so-theres-a-lot-of-angst-on-linkedin-about-activity-7308223252420509697-EJCSStevie Case: https://www.linkedin.com/in/steviecase/ Scott Albro: https://www.linkedin.com/in/scottalbro/ GongScott Barker: https://www.linkedin.com/in/ssbarker/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Sheila Stafford is the Founder and CEO of TeamSense and joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into how to land enterprise clients as a startup, how to build out a B2B sales team from scratch, and why NRR (Net Revenue Retention) is the most important metric for founders to focus on. Shelia also shares why she thinks email is a dead sales channel and why she is betting on modern PR tactics for growing TeamSense.Also, Craig shares his Instagram Shopping habits, Matt shows off his support for the Dodgers, and Sam the Producer tells a story about a field trip he went on.Critical Takeaways NRR (Net Revenue Retention) is the most important metric for startup founders because it is a direct reflection of customer love, which is the only real moat in software. When it comes to assessing new opportunities and verticals, founders need to ask themselves if it’s worth taking on a crappy client to get a short-term revenue bump, but a longer-term decrease in NRR. For Sheila and TeamSense, the answer has been a resounding, “No.”Discipline is such an important factor for founders in a number of ways, including niching down on a single vertical. This can ensure that your resources are optimally utilized, maintain a strong product-market fit, and ensure long-term sustainability and scalability of your offerings.Deep subject matter expertise in the industry you are trying to serve is invaluable. For example, Sheila's extensive experience in manufacturing allowed her to understand and address the unique challenges faced by her customers. This level of insight informed the development and marketing of TeamSense, ensuring the product met real, pressing needs.Concentrate all resources on one primary vertical before expanding to adjacent markets. TeamSense initially focused solely on manufacturing and logistics, applying all their efforts there until other verticals started showing interest naturally. This approach ensures a strong foundation before diversification.Implement a culture of continuous improvement and maintain active feedback loops. Sheila listens to her team’s Gong calls to ensure messaging remains effective and aligned with customer needs, and she provides direct feedback to her team. This practice ensures that the team continuously refines their approach based on real-time data and feedback.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Preview & Craig’s Christmas related-shirt04:21 - The Sometimes Life-saving Impact Founding a Company Can Have10:03 - Email is a Mostly Dead Channel14:17 - How to Get Your First Enterprise SaaS Deal & TeamSense’s Founding Story20:38 - Learn Your Customers' Native Language & Use It When Communicating Impact27:24 - Why Building Deep Expertise & Building Something For Someone is Critical for Startups33:11 - How Do You Measure the Value Your Product Delivers to Customers & Why Founders Need to Focus on NRR 35:45 - How to Drive Alignment Between Founders and Their Boards38:53 - How to Build out a Sales Team from Scratch & Growing Beyond Founder-Led Sales45:16 - Modern Marketing Experiments & Can PR Still Pack A Punch?Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Net revenue retention KPIs are probably one of the most important things that you should pay attention to as a founder.” - Sheila StaffordConnect with SheilaLinkedIn: https://www.linkedin.com/in/sheila-stafford-451976b/ Website: https://www.teamsense.com/ ShoutoutsFortiveVantaChristina Cacioppo: https://www.linkedin.com/in/ccacioppo/ Brett Queener: https://www.linkedin.com/in/brettqueener/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Is your main go-to-market channel driving sustainable growth? Good, double down on it, don’t start splitting up your resources into a bunch of other directions.Eric Spett is the Founder and CEO of Scalebound, providing operator-led coaching that helps CEOs scale with clarity and lead with confidence. Many in the audience may know Eric better as the Co-Founder of Terminus and his work evangelizing Account-Based Marketing. Eric joins co-hosts Craig Rosenberg and Matt Amundson to discuss the importance of focus for founders, why you shouldn’t wait to start selling until you find the perfect pricing model, and the power of in-person events and communities. Also, Craig starts hearing voices and Matt shares his encounter with Andre 3000 in an Atlanta Shake Shack.Critical TakeawaysStay focused on your primary demand channel. So many companies shift focus to secondary channels prematurely. If a primary channel like organic social selling on LinkedIn or cold calling is working well, it’s crucial to thoroughly exploit this channel before diverting resources to a new one.Avoiding "shiny object syndrome" ensures that the company’s energy and resources are directed toward proven strategies and tools that truly add value. It helps in maintaining strategic clarity and ensures the team remains aligned on critical business goals, thereby driving more sustainable growth.Don’t overcomplicate your early-stage marketing strategies. Focus on a single selling proposition. For instance, ZoomInfo successfully built its business purely on outbound tactics. Finding and honing in on the company’s single greatest strength or 'superpower' can lead to substantial growth.Building a community around your product or service can significantly enhance customer engagement and retention. In-person events are a great way to improve the activity and engagement within online communities. Structured, curated communities can lead to higher customer retention and more effective peer-to-peer marketing. This helps in creating a robust, organic promotional network that can significantly impact long-term growth and customer satisfaction.Experiment with new channels and strategies but avoid overcommitting to unproven methods at the cost of what’s already working.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 Intro01:46 Introducing Eric Spett04:21 First Deal Stories and Lessons Learned13:05 Is Your Go-to-Market motion working? Good, Keep doing it.23:47 Navigating Business Growth and Go-To-Market Strategies24:11 The AI Dilemma in Business25:41 Why LinkedIn can be A Double-Edged Sword for B2B Founders34:00 The Power of Community Building for SaaS companies46:14 Concluding Thoughts on Focus and CommunitySign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Founders, CEOs, go-to-market executives are so quick to put a lot of focus and eggs in experimental baskets when the thing that they're doing really well is still working really well. Do it and keep doing it, keep your focus.” - Eric Spett“I'm just really bullish on the need for human community and human connection.” - Eric SpettConnect withLinkedIn: https://www.linkedin.com/in/ericspett/ Website: https://scalebound.com/ ShoutoutsSangram Vajre: https://www.linkedin.com/in/sangramvajre/ TerminusAtlanta Tech VillagePhil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Scott’s Episode: https://thetransaction.substack.com/p/helping-every-founder-tell-their?r=3iae7z TOPOEverstringDavid Politis: https://www.linkedin.com/in/davidpolitis/ David’s Episode: https://thetransaction.substack.com/p/narrow-down-your-damn-icp-with-david?r=3iae7z Pavilion: Rob Forman: https://www.linkedin.com/in/robforman/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!