
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.Sponsored SegmentLorem ipsumInterested in becoming a sponsor of The Transaction? Contact [email protected]: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!
May 17, 2025
51 min

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 [email protected]: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!
May 9, 2025
57 min

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 [email protected]: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/
May 2, 2025
1 hr

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 [email protected]: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!
Apr 25, 2025
52 min

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 [email protected]: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!
Apr 19, 2025
52 min

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 [email protected]: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!
Apr 14, 2025
53 min

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 [email protected]: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!
Apr 3, 2025
49 min

It’s painfully pitiful what passes as personalized prospecting presently. However, we’ve got just the guest to help sales reps get back on the right track.Sam McKenna is the Founder of SamSales Consulting and is the foremost expert on social selling and leveraging LinkedIn to drive revenue. Sam and her team are redefining the go-to-market status quo for modern organizations through unmatched sales training and LinkedIn branding. Sam joins co-hosts Craig Rosenberg and Matt Amundson for a very fun and fascinating dive into how to improve your personalized sales messages to prospects, the secrets to successful social selling, and the best time to prospect. Plus, we share stories from some of our worst webinar fails. Also, Craig denies claims that he was in fact the heavy breather while hosting a webinar with Guy Kawasaki a decade ago and Matt reveals the truth about the size of a certain actor’s mouth.Critical TakeawaysSales reps, please take 3 seconds to THINK before sending another stinky, smelly, no-good, automated email to a prospect. If you want to stand out to them and get their attention, earn it by doing the work that none of the other reps reaching out to them won’t. Show them you know them.A simple way to stand out to decision makers at target accounts is to engage with their LinkedIn posts. However, hitting “like” does not qualify as engaging in a way that will stand out. The smart play is to comment something insightful.Prospecting during non-working hours, like weekends and evenings, can capture the attention of busy executives. Emails sent during these times can stand out because prospects are usually less overwhelmed and more likely to engage with content beyond their regular work distractions.Don’t buy a ‘great new tool’ until you know what you’re going to do with it. Figure out how to solve the problem you’re addressing before you ever get close to buying a tech solution.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 [email protected]:00 Intro Sales Insights with Sam McKenna04:38 Introducing Sam McKenna, Founder of SamSales Consulting08:02 Announcing The New Sam McKenna Award For The Best Guest10:13 A Particularly Titillating LinkedIn Controversy11:44 The Airing of Our Webinar Woes22:41 Companies Suck at Solving Problems & Try to Techstack Their Way Out of Issues28:50 How to Run the “Been Awhile” B2B Prospecting Play using LinkedIn Sales Navigator30:24 How to Use Social Selling in SaaS34:40 Spearfishing for B2B Leads Using This Tactic on LinkedIn Sales Navigator41:44 Why Putting in the Work is the Way to Wow Prospects and Customers45:50 Why the "Show Me You Know Me" Method Works so Well for B2B Sales RepsSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Why is it that so few people will just put in the actual work that that converts?” - Sam McKenna“ Anything that you can't automate won't be done.” - Matt AmundsonConnect with SamLinkedIn: https://www.linkedin.com/in/samsalesli/ Website: https://www.samsalesconsulting.com/ Sam’s new Podcast: https://www.samsalesconsulting.com/showmeyoukknowmeshow/ ShoutoutsHayley Hoad: https://www.linkedin.com/in/hayley-hoad-2565549/ Bobby Axelrod (Billions)Jill Rowley: https://www.linkedin.com/in/jillrowley/ Paige Tills: https://www.linkedin.com/in/paige-tills/ Joy Wilder Lybeer: https://www.linkedin.com/in/joywilderlybeer/ Gail Moody-Byrd: https://www.linkedin.com/in/gailmoodybyrd/ Adam Robinson: https://www.linkedin.com/in/retentionadam/ Adam’s episode of The Transaction: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal Toby Carrington: https://www.linkedin.com/in/tobycarrington/ DocuSignON24 MarketoEngagioGuy Kawasaki: https://www.linkedin.com/in/guykawasaki/ Jon Gray: https://www.linkedin.com/in/jon-d-gray/ DailyMail Article about the “LinkedIn Boobs Post”: https://www.dailymail.co.uk/news/article-14406563/linkedin-post-fury-comparing-woman-breast-size-confidence.html Bobby Axelrod/Damian Lewis Tiny Mouth Investigation: https://www.maxim.com/entertainment/damian-lewis-tiny-mouth-2016-3/ Reddit discussion of Bobby Axelrod/Damian Lewis’s tiny mouth: https://www.reddit.com/r/Billions/comments/8jcnx5/anyone_else_getting_annoyed_by_damian_lewis_tiny/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
Mar 28, 2025
56 min

You’ll be hard pressed to find a more energetic and experienced sales expert than our special guest, Maria Boulden!Maria Boulden has spent over 3 decades creating and leading world-class sales teams at leading enterprise organizations like DuPont and Gartner. She brings her incredible experience in multiple verticals and truly unstoppable energy to one of the best conversations yet with co-hosts Matt Amundson and Craig Rosenberg. Maria drops some serious insight bombs in this one, including why steak dinners aren’t the deal closer that they once were, why top execs need to get down to the frontlines to talk with employees, and why ‘not broken’ is not good enough for your company to succeed. Additionally, there is some great advice in here about effectively leading change management efforts in your organization, why building personal relationships in SaaS has become so important for B2B sellers, and why you shouldn’t hold a deal signing at a Japanese gentleman’s club. Fueled by an ungodly amount of Coke Zero, Maria really brought it this episode and delivered some incredible stories, which make this a must-watch!Also, Craig tests out a new hat and Matt admits he can be bought with a burrito. Critical TakeawaysSenior leaders need to be visibly and vocally present with front-line sellers periodically. This not only boosts team morale but also ensures the leader understands the day-to-day challenges and can directly impart strategic guidance.Sales teams should focus on providing value and building genuine connections rather than relying on traditional wining and dining strategies.Waiting for 'normalcy' to return so you go back to old tactics is not viable. Leaders must guide their teams to adapt to the current market conditions and be prepared for continuous change.Conducting “pre-mortem” sessions can be an effective way to anticipate potential failures and mitigate risks before executing significant strategic changes. This approach can foster an environment of proactive problem-solving and better preparedness among the team.Helping clients understand their own business better and providing insights creates stronger, more trusting client relationships.Sponsored SegmentThe 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]:00 Intro00:44 Craig’s Special Hat02:35 Introducing Maria Boulden10:39 The Challenge with Channel Partners19:31 Brazenly Baring It All23:03 A Quick Conversation Regarding Caffeine23:43 Steak Dinners have Gone Stale in Sales33:42 Stories from the Signing Party & Where NOT to Hold One36:48 Taking a Hands-on Approach to Leadership in Sales38:17 Unbatten the Hatches & Adapting to Market Changes41:56 How Executives Should Engage with Their Sales Teams50:59 Delving into some Delicious Additions to Business Dictionaries55:30 Wrapping UpSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ It was not my aspiration that they would have world-class sales skills, it was my expectation.” - Maria Boulden“ Not broken is not good enough in this environment.” - Maria BouldenNew TermsDonut Run (v): When a rep brings a box of joe and a box of donuts to meet with their distributor and ‘shoot the breeze’ for an hour.Ask Hole (n): Someone who continuously asks the same question, but never does anything with the suggestions they receive.Pre-Mortem (n): A proactive meeting held before executing a decision, campaign, etc., where the risks are clearly laid out along with what indicators should be monitored to determine real-time progress and what actions need to be taken mid-course.Connect with MariaLinkedIn: https://www.linkedin.com/in/maria-boulden-8a778b11/ Website: https://www.jsjrehoboth.com/ ShoutoutsDan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan’s Post: https://www.linkedin.com/posts/danielpgottlieb_good-luck-with-that-ai-theres-no-ai-on-activity-7293698734540955648-rNIz Dan’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z Nick Toman: https://www.linkedin.com/in/nicktoman/ Nick’s Episode: https://thetransaction.substack.com/p/the-commercial-efficiency-crisis?r=3iae7z Neil RackhamSpin Selling: https://a.co/d/1FSFtS1 Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ Kyle Porter: https://www.linkedin.com/in/kyleporter/ Kyle’s Episode: https://thetransaction.substack.com/p/startup-stunts-and-loving-your-customers?r=3iae7z Brent Adamson: https://www.linkedin.com/in/brentadamson Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z Ted Purcell: https://www.linkedin.com/in/tedpurcell/ Bill McDermott: https://www.linkedin.com/in/billrmcdermott/ GartnerDuPontSalesforceLove the show? Give us a shoutout on LinkedIn and tell us what you loved!
Mar 20, 2025
58 min

Michael King is one of the leading marketing executive recruiters working today and is also the author of a new book, Be There When I Return, a memoir of epilepsy, love, and success. Michael joins co-hosts Craig Rosenberg and Matt Amundson to discuss his personal journey with both epilepsy and his career, along with crucial career advice for marketing leaders looking for their next roles. Michael shares how the CEO should factor into your job search, why you shouldn’t chase titles, and the state of the job market for B2B marketing executives.Also, Craig tries out a new look and Matt relives an epic beach party in Vegas.Critical TakeawaysEnsure the people you hire have relevant experience at companies similar in size and stage to your own. Avoid hiring someone just because they’ve been part of a larger company’s success unless their role aligns directly with what your company needs now.Chase companies over titles. Titles shouldn't be the defining factor when considering new positions. Joining a strong, growing company should be the priority as it offers career growth opportunities in the long run. Focus on the company's potential rather than the initial title, as the ultimate career growth lies in sustainable company success.Sponsored SegmentThe 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]:00 Intro02:58 Introducing Michael King04:15 Michael's New Book & Incredible Personal Journey09:29 Recruiting Career & Success Stories18:54 Amazing Event Marketing Anecdotes27:44 Falling in Love with a Brand28:33 The Importance of Relevant Experience33:55 Chasing Titles vs. Chasing Companies39:14 The Value of Good Companies49:03 Epilepsy Awareness and Personal StoriesSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ If you go to a good company, you will never look for a job again.” - Michael King“ For success in your career, you chase companies, you do not chase titles; you do not chase money, you chase companies” - Michael KingConnect with MichaelLinkedIn: https://www.linkedin.com/in/michaelking/ Website: https://kingrecruiting.net/ Book Website: https://www.michaeltking.com/ Book signing in San Francisco: https://www.bookpassage.com/event/michael-king-be-there-when-i-return-ferry-building-store ShoutoutsGeorge WallaceMaria PergolinoWill Smith & DJ Jazzy Jeff Reunion at Everstring’s Pool Party: https://youtu.be/v6-QoeusjEs?si=2CynMyahkkqG1mT8 Jessica CrossStephanie Stacey EpsteinDavid Mylam Dave ArnoldMichael LundgrenMiles KellyRob BernsteinUdi LedergorRussell UdySuccessFactorsSalesforceBroadvisionOktaCoupaSiebelGongCrestaLove the show? Give us a shoutout on LinkedIn and tell us what you loved!
Mar 17, 2025
56 min
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