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

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ Really strong quality work and great execution never goes out of style, no matter what the trend is and what's working.” - Amy Holtzman
• “If you want to sell things, make sure you have enough salespeople.” - Amy Holtzman
• “I rub the thing” - Craig 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/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

AI use cases & tactics are moving at a million miles per hour which can make it hard to adopt some of these amazing innovations into your go-to-market strategy. Thankfully, we knew just the guy to have on the show to help us put into practice what otherwise could seem like technological mumbo, and or jumbo.

That man’s name is Jordan Crawford, the Founder of Blueprint GTM and one of the foremost go-to-market engineers innovating B2B sales and marketing on the cutting edge of AI advancements.

Jordan joins co-hosts Craig Rosenberg and Matt Amundson to dive into where we’re thinking about our go-to-market strategy and tech stack in the wrong way, how to segment cold outbound leads in an effective, yet scalable way based on pain, and how to evolve your revenue organization to excel in the new, ai-powered world.

Also, Craig shows off his sandwich shop shirt, Matt gets on yet another soapbox, and Producer Sam is asked for his opinion.

Critical 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.

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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

Sign 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 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

Sign 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 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 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Not a long time ago in a Silicon Valley not too far away, the sales infrastructure of almost every startup was an immature, undisciplined mess… Until a certain former printer salesman turned up in town…

Lars Nilsson is the Founder and CEO of SalesSource, but you probably know him from his legendary run as the VP of Global Sales Development at Snowflake. To Craig, Lars is, “one of the masters of the universe in sales development and inside sales and business, and clearly very fit.” Lars joins co-hosts Craig Rosenberg and Matt Amundson to discuss how we got to the current state of sales training and enablement in B2B SaaS, why the GTM Engineer role is the next hire you need to make to improve your revenue team, and whether having B2B sales reps roleplay with AI avatars is the way forward or just a waste of time.

Also, Craig relives stories of his past mastication, Producer Sam fights yet another losing battle, and Matt warns everyone that, “ we're going to go deep. We're going deep.”

Critical 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

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Ana Leyva advises early-stage startups at Pear VC on their go-to-market strategy to help them build stunning sales motions that set them up to scale. Ana provides pre-seed and seed startups with her first-hand experience as a seasoned operator with past roles at tech unicorns Box, ServiceTitan, and Vanta. Ana joins Co-Hosts Craig Rosenberg and Matt Amundson to delve into how to transition beyond a founder-led sales motion without losing their special perspective, why insight-driven outreach beats crappy sales personalization in B2B, and the two foundational pillars that you need to have in place to build a strong go-to-market strategy.

Additionally, Ana details the importance for founders to be extremely disciplined with their Ideal Customer Profile and who they allow to steer the course of the future of their company.

Also, Craig gets a ton of text notifications, and Matt muses about buying Craig a present for Easter.

Critical Takeaways

• The 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 Segment

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

Chapters

00:00 - Episode Preview

00:20 - Squishy Pineapples & The 1995 UCLA Bruins

04:01 - Introducing Ana Leyva, GTM Leader at Pear VC

08:29 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 Playbooks

27:24 - Scaling Your Sales Team & Shifting from Founder-led Sales

34:53 - Discipline is a Founder’s Best Friend & Going Narrow is the Way to Win as a Startup

45:06 - 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 Leyva

Connect with Ana

• LinkedIn: https://www.linkedin.com/in/analeyva/ 
• Pear VC Website: https://pear.vc/ 

Shoutouts

• AJ 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-EJCS
• Stevie Case: https://www.linkedin.com/in/steviecase/ 
• Scott Albro: https://www.linkedin.com/in/scottalbro/ 
• Gong
• Scott Barker: https://www.linkedin.com/in/ssbarker/ 
• Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Sheila Stafford is the Founder and CEO of TeamSense and joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into how to land enterprise clients as a startup, how to build out a B2B sales team from scratch, and why NRR (Net Revenue Retention) is the most important metric for founders to focus on. Shelia also shares why she thinks email is a dead sales channel and why she is betting on modern PR tactics for growing TeamSense.

Also, Craig shares his Instagram Shopping habits, Matt shows off his support for the Dodgers, and Sam the Producer tells a story about a field trip he went on.

Critical Takeaways

•  NRR (Net Revenue Retention) is the most important metric for startup founders because it is a direct reflection of customer love, which is the only real moat in software. When it comes to assessing new opportunities and verticals, founders need to ask themselves if it’s worth taking on a crappy client to get a short-term revenue bump, but a longer-term decrease in NRR. For Sheila and TeamSense, the answer has been a resounding, “No.”
• Discipline is such an important factor for founders in a number of ways, including niching down on a single vertical. This can ensure that your resources are optimally utilized, maintain a strong product-market fit, and ensure long-term sustainability and scalability of your offerings.
• Deep subject matter expertise in the industry you are trying to serve is invaluable. For example, Sheila's extensive experience in manufacturing allowed her to understand and address the unique challenges faced by her customers. This level of insight informed the development and marketing of TeamSense, ensuring the product met real, pressing needs.
• Concentrate all resources on one primary vertical before expanding to adjacent markets. TeamSense initially focused solely on manufacturing and logistics, applying all their efforts there until other verticals started showing interest naturally. This approach ensures a strong foundation before diversification.
• Implement a culture of continuous improvement and maintain active feedback loops. Sheila listens to her team’s Gong calls to ensure messaging remains effective and aligned with customer needs, and she provides direct feedback to her team. This practice ensures that the team continuously refines their approach based on real-time data and feedback.

Sponsored 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 - Preview & Craig’s Christmas related-shirt

04:21 - The Sometimes Life-saving Impact Founding a Company Can Have

10:03 - Email is a Mostly Dead Channel

14:17 - How to Get Your First Enterprise SaaS Deal & TeamSense’s Founding Story

20:38 - Learn Your Customers' Native Language & Use It When Communicating Impact

27:24 - Why Building Deep Expertise & Building Something For Someone is Critical for Startups

33:11 - 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 Boards

38:53 - How to Build out a Sales Team from Scratch & Growing Beyond Founder-Led Sales

45:16 - Modern Marketing Experiments & Can PR Still Pack A Punch?

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Epic Quotes

• “ Net revenue retention KPIs are probably one of the most important things that you should pay attention to as a founder.” - Sheila Stafford

Connect with Sheila

• LinkedIn: https://www.linkedin.com/in/sheila-stafford-451976b/ 
• Website: https://www.teamsense.com/ 

Shoutouts

• Fortive
• Vanta
• Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/ 
• Brett Queener: https://www.linkedin.com/in/brettqueener/ 

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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 Takeaways

• Stay 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 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 Intro

01:46 Introducing Eric Spett

04:21 First Deal Stories and Lessons Learned

13:05 Is Your Go-to-Market motion working? Good, Keep doing it.

23:47 Navigating Business Growth and Go-To-Market Strategies

24:11 The AI Dilemma in Business

25:41 Why LinkedIn can be A Double-Edged Sword for B2B Founders

34:00 The Power of Community Building for SaaS companies

46:14 Concluding Thoughts on Focus and Community

Sign 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 Spett

Connect with

• LinkedIn: https://www.linkedin.com/in/ericspett/ 
• Website: https://scalebound.com/ 

Shoutouts

• Sangram Vajre: https://www.linkedin.com/in/sangramvajre/ 
• Terminus
• Atlanta Tech Village
• Phil 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 
• TOPO
• Everstring
• David 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/ 

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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 Takeaways

• Sales 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 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 Intro Sales Insights with Sam McKenna

04:38 Introducing Sam McKenna, Founder of SamSales Consulting

08:02 Announcing The New Sam McKenna Award For The Best Guest

10:13 A Particularly Titillating LinkedIn Controversy

11:44 The Airing of Our Webinar Woes

22:41 Companies Suck at Solving Problems & Try to Techstack Their Way Out of Issues

28:50 How to Run the “Been Awhile” B2B Prospecting Play using LinkedIn Sales Navigator

30:24 How to Use Social Selling in SaaS

34:40 Spearfishing for B2B Leads Using This Tactic on LinkedIn Sales Navigator

41:44 Why Putting in the Work is the Way to Wow Prospects and Customers

45:50 Why the "Show Me You Know Me" Method Works so Well for B2B Sales Reps

Sign 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 Amundson

Connect with Sam

• LinkedIn: https://www.linkedin.com/in/samsalesli/ 
• Website: https://www.samsalesconsulting.com/ 
• Sam’s new Podcast: https://www.samsalesconsulting.com/showmeyoukknowmeshow/ 

Shoutouts

• Hayley 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/ 
• DocuSign
• ON24 
• Marketo
• Engagio
• Guy 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!

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 Takeaways

• Senior 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 Segment

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 Intro

00:44 Craig’s Special Hat

02:35 Introducing Maria Boulden

10:39 The Challenge with Channel Partners

19:31 Brazenly Baring It All

23:03 A Quick Conversation Regarding Caffeine

23:43 Steak Dinners have Gone Stale in Sales

33:42 Stories from the Signing Party & Where NOT to Hold One

36:48 Taking a Hands-on Approach to Leadership in Sales

38:17 Unbatten the Hatches & Adapting to Market Changes

41:56 How Executives Should Engage with Their Sales Teams

50:59 Delving into some Delicious Additions to Business Dictionaries

55:30 Wrapping Up

Sign 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 Boulden

New Terms

• Donut 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 Maria

• LinkedIn: https://www.linkedin.com/in/maria-boulden-8a778b11/ 
• Website: https://www.jsjrehoboth.com/ 

Shoutouts

• Dan 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 Rackham
• Spin 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/ 
• Gartner
• DuPont
• Salesforce

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!