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 Takeaways

• Building 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.

Chapters

00:00 - Episode Preview

00:50 - Endearing Terms for The Wonderful People from Massachusetts

03:27 - Introducing Rachel Dines, Author & Go-To-Market Advisor (Plus, Former Forrester Analyst)

07:24 - A Quick Convo about Data Centers & The Mission Impossible Film Franchise

10:24 - Giving Your First Solo Presentation as an Analyst with a Heads Up

16:18 - Why Startups Need To Engage The Industry Analysts Early On

20:22 - How Startups Should Approach Their Initial Analyst Relations Strategy

29:35 - Matt Admits What Grinds His Gears

31:23 - What Early Stage Startups Can do to Become Number One in the Magic Quadrant

34:08 - Startups Should Start with One Segment, User, and Use Case

46:51 - Why Your First Marketing Hire Should be a Product Marketer

52:21 - Some not so great B2B Marketing career advice

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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 Dines

Connect with Rachel

• LinkedIn: 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 

Shoutouts

• Scott 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/ 
• Cursor
• Windsurf
• Lovable
• Chris Degnan: https://www.linkedin.com/in/chris-degnan-524470/ 
• Snowflake
• Denise Persson: https://www.linkedin.com/in/denisepersson/ 

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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 Takeaways

• What 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.

Chapters

00:00 - Episode Preview

03:51 - Introducing Tom Murtaugh, Portfolio Operations Director at Nordic Capital

10:09 - How Improving Deal Control Turned Around a Terrible Quarter for Collibra

21:02 - Understanding the Key Activities that Really Drive Outcomes in B2B Sales

28:21 - Why Training First Line Sales Managers Needs to be a Priority for B2B GTM Leaders

42:29 - Why the Sales Enablement Movement Ultimately Failed in Improving B2B Sales Orgs

51:21 - The Role of RevOps in Building a Sustainable Infrastructure for the Revenue Organization

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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 Murtaugh

Connect with Tom

• LinkedIn: https://www.linkedin.com/in/tom-murtaugh-1729b09/ 
• Nordic Capital Website: https://www.nordiccapital.com/ 

Shoutouts

• Amanda Murtaugh: https://www.linkedin.com/in/amandabuck143/ 
• Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ 
• Philip Cardi
• Neil 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)

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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 Takeaways

• Investing 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.

Chapters

00:00 - Episode Preview

02:21 - Introducing Chris Orlob, CEO of pclub.io

03:33 - An Instructive B2B Sales Story: How to Interact with Procurement Leaders

08:06 - Craig & The Case of The Bloody-Eyed Business Meeting

12:19 - The State of the B2B Sales Skills Crisis in Go-To-Market Today

25:40 - Discovery is the Fundamental Sales Skills Reps Need to Learn

33:24 - How B2B Companies Should be Approaching Discovery and the Buying Process in Today's Market

44:25 - Why B2B Sales Leaders Need to Implement a Skill Transformation Loop Into Their Teams' Training

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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 Amundson

Connect with Chris

• LinkedIn: https://www.linkedin.com/in/chrisorlob/ 
• pclub.io Website: https://www.pclub.io/
• Twitter: https://twitter.com/Chris_Orlob 

Shoutouts

• Chris’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/ 

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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 Takeaways

• When 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.

Chapters

00:00 - Episode Preview

01:32 - Introducing David Boskovic, The CEO & Founder of Flatfile

02:49 - The Crazy, Raccoon-Filled Story Behind David Starting His First Company

11:35 - Building an AI-First Go-To-Market Engine Internally from Scratch 

15:07 - AI Lets You Do The ‘Unscalable’ At Scale with Quality and Affordability

22:02 - Why Segmenting Prospects into Micro-Verticals Increases Your ABM Strategy’s Effectiveness

33:26 - What it Takes to Spin Up an AI-First GTM Strategy & Why RevOps Teams Need an AI Engineer

39:57 - Where is Software Going & Which of The 3 Ways to Implement AI Works Best

47:12 - Why You Should Be Hiring Individual Contributors Based on Their Judgement

51:34 - Sam Debuts Some Interesting AI Artwork of David

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Epic Quotes

• It 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 Amundson

Connect with David

• LinkedIn: https://www.linkedin.com/in/dboskovic/ 
• Website: https://flatfile.com/ 

Shoutouts

• Rory 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 Takeaways

• 80% 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.

Chapters

00:00 - Episode Preview

00:48 - Introducing Sydney Sloan, Chief Market Officer at G2

04:15 - The Emerging Go-To-Market Playbook & New B2B Buyer Behavior Study

11:25 - 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 Creatively

21:59 - How Buyers are Using AI Tools In Their Buyer Journey & To Compare Solutions

26:47 - How Generative Engine Optimization Helps Your Brand Show Up in AI Search Results

31:59 - Why Enterprises are Using AI Tools More Than Startups

33:53 - The Meteoric Rise of Cursor & Which Categories or Niches are Ripe for AI Disruption

44:24 - The AI Gradient & Why You Need an AI Architect on Your RevOps Team

50:21 - Throwing Craig Under The Bus For Causing a Technical Issue & Wrapping Up

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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 Amundson

Connect with Sydney Sloan

• LinkedIn: 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 

Shoutouts

• Kyle 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 Cabane
• Cursor: www.cursor.so
• Qualified: www.qualified.com
• Clay: www.clay.com
• HubSpot: www.hubspot.com
• 1mind: www.1mind.com
• Salesloft: www.salesloft.com
• Gong: www.gong.io
• Iron Mountain: www.ironmountain.com
• Airbnb: www.airbnb.com
• Waze: www.waze.com
• Uber: www.uber.com
• Lovable: www.lovable.so 
• Windsurf: www.windsurf.ai 
• Waymo: www.waymo.com 

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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 [email protected]

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  

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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/ 

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 Takeaways

• Encouraging 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.

Chapters

00:00 Intro

01:09 Introducing Justin Michael and Charles Needham

02:55 Discussing B2B Sales Strategies and Cold Calling as an effective sales channel

03:37 Justin's B2B Sales Stories and Experiences

08:07 Charles on Modern Sales Challenges for SaaS Startups

13:22 The Emerging Role of AI in B2B Sales Today

17:10 Cold Calling Sales Techniques and Best Practices

30:29 Debating Cold Call Openers

32:53 Unified Theory of Cold Calling for B2B sales

39:03 Mastering Tonality and Rhythm during B2B Sales Calls

56:26 The Future of Cold Calling

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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 Michael

Connect with Justin Michael

• LinkedIn: https://www.linkedin.com/in/michaeljustin/ 
• Website: https://www.salesborgs.ai/ 
• Get the Book: https://coldcallalgo.com/ 

Connect with Charles Needham

• LinkedIn: https://www.linkedin.com/in/charles-needham/ 
• TitanX Website: https://www.titanx.io/ 

Shoutouts

• Kai-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.ai
• Mike Bosworth: https://www.linkedin.com/in/mikebosworth/ 

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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.'

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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 Takeaways

• Train 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.

Chapters

00:00 - Episode Preview

00:36 - The Fast & The Furious: Silicon Valley Drift

07:39 - Two Insightful Examples of How B2B Companies are Using & Operationalizing Gen AI

11:41 - 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 Officer

16:08 - The Power of Building Custom AI Agents for Revenue Growth

22:22 - B2B Sales Leaders are Still Getting Stuck on Activity Metrics, When They Should Measure Impact

30:04 - How to Construct a Successful B2B Outbound Strategy in the Current Market

37:01 - 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 Advancements

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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 Dunlap

Connect with Jake Dunlap

• LinkedIn: https://www.linkedin.com/in/jakedunlap/ 
• Website: https://skaled.com/ 
• The Innovative Seller (Jake’s Book): https://www.jakedunlap.com/the-innovative-seller 

Shoutouts

• Dirty 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.
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