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 

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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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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 Takeaways

• The 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.

Chapters

00:00 Episode Preview

03:30 – The Go-To-Market Founder Concept

07:00 – How Modern Go-To-Market Orgs Win

13:00 – Growth Bets: What They Are and Why They Matter for B2B Marketers

17:00 – Crafting a Resonant Story for your B2B brand

21:00 – Aligning Product and Go-To-Market Motions (Finally)

25:00 – Convincing B2B Startup CEOs to Experiment

30:00 – Bland’s Viral Growth and the “Stunt Marketing” Debate

36:00 – Storytelling Frameworks That Actually Work for Startups

42:00 – Lethal Weapon Posters and Swarms of Bees

Epic Quotes

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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 Albro

Connect with Scott

• LinkedIn: https://www.linkedin.com/in/scottalbro/ 

Shoutouts & Resources Mentioned

• Skosh: 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=3
• Bland
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• Tricia Gellman: https://www.linkedin.com/in/gellmansfmarketing/ 
•  Lena Waters: https://www.linkedin.com/in/lenawaters/

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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 Takeaways

• 
  Instead 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.

Chapters

00:00 Episode Preview

03:30 The GTM Midlife Crisis Hits – Why the old playbooks stopped working

06:15 Building a New Playbook with AI in the Go-To-Market Hacker era

08:45 Matt’s AI Buyer Persona Workflow – How to build and deploy AI agents for feedback

13:15 Talk to Your AI Tools Like People 

17:00 999/1000 Accuracy Rate – Why AI is now a mission-critical content editor

25:30 Account Research is the New Minimum – How GTM teams are winning with better prep

30:00  Matt & Craig just Want to Watch the World Burn

37:00 Events Are Back, Baby – People crave new insights and in-person energy

40:00 LinkedIn has changed, but it is still the social platform of choice for B2B brands

45:00 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 him

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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 Amundson

Shoutouts

• Maria 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 
• SaaStr
• Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ 
• Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ 
• Copy.ai
• Klarity: 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=false

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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 Takeaways

• Events 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 experiences
• Prospects 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.

Chapters

00:00 - Episode Teaser

00:34 - Amy’s Amazing Hat, Chain Restaurant Pub Crawls, & the Apollo Theater

10:36 - Introducing Amy Holtzman, Chief Marketing Officer at CHEQ

13:46 - Lessons to Learn from the Worst Sales Experience Ever

25:53 - Search is Still Driving A Surprising Amount of Enterprise Deals

30:50 - Breaking Down the New G2 Research on B2B Buying Behavior & How AI is Impacting Vendor Shortlists

35:08 - How to Get More ROI from your Event Strategy & Field Marketing Mistakes to Avoid

39:46 - Sponsoring Niche Events can Pack a Massive Punch for Smaller B2B Brands

44:44 - Thinking Beyond the Booth When Planning out Your Event Strategy

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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 Rosenberg

Connect with Amy

• LinkedIn: https://www.linkedin.com/in/aholtzman/ 
• Website: https://cheq.ai/ 

Shoutouts

• Every 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-report
• Sydney 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/ 

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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 Takeaways

• Identify 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.

Sponsored Segment

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Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Introduction: The Intimidating Box

01:07 Mr. Pickles and Misadventures in Pocket Dialing

04:42 Craig’s Midlife Go-To-Market Crisis

05:31 What’s broken with the Old Go-To-Market Playbooks

07:30 What is The New World of Sales and AI

13:04 Segmenting and Targeting with Data

16:43 Permissionless Value Prop in Action

23:25 The List is the Message

25:47 Methodology and AI Integration

26:55 Understanding Customer Segments

29:56 Challenges in Sales and Marketing

33:18 Effective Campaign Strategies

35:16 Adapting to AI and Market Changes

38:37 Purpose of Niche Targeting and Success

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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 Crawford

New Terms

• Pain Qualified Segment: Two to five unique heuristics, often that imply tension.

Connect with Jordan

• LinkedIn: 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 

Shoutouts

• Scott 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 Takeaways

• Develop 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 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 [email protected]

Chapters

00:00 Episode preview

00:30 Craig Goes Batty and Some Auction Antics

04:13 Introducing Matt Heinz, President of Heinz Marketing

08:07 B2B Marketers are Terrible at Naming Concepts, Products, and Strategies

19:16 Should CMOs Report Up to CROs in B2B SaaS?

22:03 Ranking the Best Hair Amongst Men in B2B & Matt Confesses to Rocking a Mullet

27:27 How Go-To-Market Teams are Using AI & Evolving Their GTM Strategy with AI

37:13 Trust & Personal Relationships are Differentiators in the Age of AI Marketing Tools

42:11 The Role of Data & The Cloud Data Warehouse in B2B Marketing

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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 Amundson

Connect with Matt Heinz

• LinkedIn: https://www.linkedin.com/in/mattheinz/ 
• Website: https://www.heinzmarketing.com/ 

Shoutouts

• Bat 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 Robotics
• Mperativ
• Brent Adamson: https://www.linkedin.com/in/brentadamson/ 
• Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z 

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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 Takeaways

• Recognize 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 [email protected]

Chapters

00:00 - Episode Preview

00:35 - Craig Eats like Cookie Monster

03:13 - Introducing Lars Nilsson, the Founder & CEO of SalesSource and Former VP of Global Sales Development at Snowflake

07:46 - The Genesis of Sales Development in SaaS & How it Expanded on Account-Based Marketing Concepts

13:23 - How Xerox Trained Their B2B Sales Team and What Startups Should Learn from Their Success

21:34 - The Emerging GTM Engineer Role & The Impact Its Having on B2B Sales Teams Using AI Tools

34:59 - Should B2B Startups Try to Replicate the SDR Academy from Snowflake

38:17 - How Startup Leaders Can Elevate the SDR Role & Why They Must Show Their Appreciation for this Critical Function

45:42 - The Importance of AI Roleplaying Tools for Training B2B Salespeople

54:11 - Startups Founders Should Play a More Active Role in Developing Their Go To Market Strategy

Sign 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 Nilsson

Connect with Lars

• LinkedIn: https://www.linkedin.com/in/lanilsson/ 
• SalesSource Website: https://salessource.com/ 

Shoutouts

• Stuart 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 Takeaways

• Implement 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 Segment

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 - Episode Preview

00:30 - Are the Angels a Real Team & Breaking Down the Backgrounds

03:24 - Introducing Lauren Goldstein, Chief Growth Officer of Winning By Design & Co-Founder of Women in Revenue

06:36 - The Origin Story of Women in Revenue (The group, not the concept)

18:17 - The Immutable Impact Diverse Teams in Business

23:43 - B2B Tech Brands Are NOT Connecting Buyers in the Ways That SaaS Buyers Want

31:39 - What is a ‘Reverse Demo’ & Why is Gartner Analyst Dan Gottlieb Recommending it

36:00 - Revenue Growth in SaaS Comes Back to Identifying the Right Buyers

40:43 - The Critical Role of Rev Ops in B2B Go-to-Market Strategy for SaaS

44:00 - Strategic Rev Ops: The Key to Integration & Go-To-Market Alignment

Sign 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 Lauren

• LinkedIn: https://www.linkedin.com/in/laurengoldstein/ 
• Winning by Design Website: https://winningbydesign.com/ 
• Women in Revenue Website: https://womeninrevenue.org/ 

Shoutouts

• Sydney 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/ 
• Radius
• Marketo
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• InsideView
• Babcock Jenkins
• Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ 
• Dan’s Episode: ​​https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb 
• Miro
• Mark 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/ 
• Socure
• Adam 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 
• Annuitas

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