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The Transaction

The Transaction

Matt Amundson & Craig Rosenberg

Welcome to The Transaction. The #1 Go-To-Market podcast on the planet. Hosts Craig Rosenberg and Matt Amundson, two legendary go-to-market leaders in their own right, talk weekly with the best sales, marketing, operations, and product leaders in the B2B SaaS world to understand what's working in the new playbook of the post-ZIRP market. But Craig, Matt, and their guests don't just talk theoretically, they share the stories and actionable tips, tactics, and strategies behind what's driving revenue growth that you can take and implement in your own go-to-market roles. From ABM to PLG, from MEDDIC to MEDDPICC, the world of business is constantly evolving. We’ll cover the who, what, where, when, why and most importantly how you get... The Transaction.
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Top 10 The Transaction Episodes

Goodpods has curated a list of the 10 best The Transaction episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to The Transaction for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite The Transaction episode by adding your comments to the episode page.

Joining Craig Rosenberg and Matt Amundson in Episode 5 is special guest Chris Orlob, the Co-Founder & CEO of pclub.io. Many of you probably know about Chris or his awesome work early on at Gong which helped the company reach hockey stick level growth. Chris shares his “unqualified” thoughts on when to gate content, how to get deals done on demo calls, and what prime sales prospecting outreach should look and feel like.

Also, Craig compares himself to a cartoon image on a coffee mug and Matt mixes up two timeless classic holiday films.

Takeaways:

  • Some of the best prospecting messages don't even like talk about the product, its benefits, or your company. For example, a good prospecting email could be: [A very well articulated grasp of the challenges they're probably going through] and we've been able to help a bunch of other companies solve this. Is this challenge worth a live chat?
  • “It's not multi threading, it's single threading with multiple people.”

Chapters:

  • 00:00 - Comparing Craig’s Mug to Craig’s Mug
  • 07:24 - Customer at the Gates: Dodging the Ungated Content Dogma
  • 14:30 - Mastering Multi-Threading in B2B Sales
  • 28:16 - Demystifying the Sales Deck
  • 31:24 - Crafting the Perfect Prospecting Email
  • 37:06 - When to Demo & How to Run That Call
  • 48:00 - Negotiations: What Happens when there’s now Win-Win?

Quote of the Show:

  • “I'm like the world's least qualified marketer of all time, but I still have strong opinions about it.” - Chris Orlob

Sponsor:

Connect with Chris Orlob:

Shoutouts:

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Our special guest today is a three-time CMO and seasoned veteran in the customer experience and SalesTech world who offers CX and sales software companies a wealth of expertise that he has accumulated over several decades. Nicolas de Kouchkovsky is a Fractional Chief Marketing Officer & Industry Analyst at CaCube Consulting. Nicolas joins Hosts Craig Rosenberg and Matt Amundson to discuss the transition from traditional methods to Signal-based Selling and the urgent need for precision and relevance in outbound sales efforts. They also dive into the critical role of modern data architectures, such as cloud data warehouses, in enabling efficient and effective sales strategies, stressing the importance of moving beyond CRM as the system of record to embrace more flexible, data-rich platforms.

Also, Craig makes a re-introduction and Matt sets the record for the number of times a person has said data warehouse on a podcast.

Takeaways:

  • The transition towards signal-based selling highlights the need for marketers to adapt to advanced methods of identifying and engaging with potential customers. The ability to harness and interpret signals can significantly improve targeting and personalization.
  • Precise market segmentation and pinpointing the Ideal Customer Profile (ICP) are more crucial than ever. Generic approaches are no longer effective. Teams should invest time in deeply understanding their target segments to tailor messages and offers accordingly.
  • Crafting and communicating a clear, compelling value proposition is essential. Vague statements about benefits can undermine trust. Marketers must articulate how their products or services address specific customer needs and pain points.

Chapters:

  • 00:59 Reintroducing Nicolas De Kouchkovsky
  • 02:34 Understanding Signal-based Selling
  • 11:57 The CRM As The System of Record
  • 27:23 Automation and Precision: The Future of Outbound
  • 34:41 The Lost Art of Segmentation
  • 44:11 AI’s Role is to Assist the Seller
  • 49:11 Get Rid of Mushy Messaging

Quote of the Show:

  • “If you start a business right now, your data should be the foundation and it will be your mid to long-term sustainable differentiator against any legacy business” - Nicolas de Kouchkovsky

Sponsor:

Connect with Nicolas:

Shoutouts:

Follow the Show:

Ways to Tune In:

YouTube: https://www.youtube.com/@TheTransa...

To help you wrap your head around the rapidly evolving technological landscape as a revenue leader, we have a very special guest today. Mary Shea is the former Principal Analyst at Forrester and is currently advising and coaching multiple high-growth companies. Mary joins Hosts Craig Rosenberg and Matt Amundson to discuss the technology-enabled future of B2B sales organizations, which stages of the funnel should be automated first, and understanding “Signal-based Selling.”

Also, Craig relishes getting a great compliment and Matt is put on the hot seat for one of his takes on B2B sales.

Takeaways:

  • Investing in sales training and enablement is vital, both internally and via third parties. This focus on upskilling is critical during times of change, especially as enablement professionals are among the first to be let go when budgets are tight. Consistent investment in enablement is key to maintaining a high-performing sales team.
  • Look beyond point solutions to vendors who offer comprehensive support for the sales cycle. Try to work with vendors who possess an exciting vision for the future, particularly those who incorporate embedded and generative AI into their offerings, allowing for a more consolidated and efficient tech stack.
  • Focus on insights over mere data to improve buyer-seller interactions. It’s much more important to extract meaningful insights from data, than just collect data for its own sake. The term 'Signal-based Selling' highlights the need for sales and marketing professionals to focus on actionable insights that drive meaningful engagements with prospects and customers.

Chapters:

  • 00:00 - Craig is called a “Living Legend”
  • 01:23 - Introducing special guest Mary Shea
  • 03:30 - The Agile, Tech-Enabled Salesforce
  • 10:51 - Are Smaller Sales Teams the Future?
  • 13:12 - Can You Scale Back on SDRs & Sell More?
  • 17:41 - How Sales Leaders should Think about Automation Today
  • 21:19 - Is Greater Specialization in Sales the Solution?
  • 29:18 - The Emerging SE Tech Stack
  • 34:05 - Embracing Gen AI in the Enterprise
  • 44:51 - Understanding Signal-Based Selling

Quote of the Show:

  • “If I’m a revenue leader ... I need to think about technology as another arrow in my quiver.” - Mary Shea

Sponsor:

Connect with Mary:

Shoutouts:

Follow the Show:

Ways to Tune In:

YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1

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As a GTM leader, you’re probably working every day to improve your playbook and you’re not alone. If improving your sales motions is a serious priority, you should probably check out this episode. Doug Landis is the CEO of DL Advisory and both a renowned sales professional and storyteller. Doug joins Co-Hosts Craig Rosenberg and Matt Amundson for a B2B sales and messaging masterclass, including an explainer of his Hypothesis Selling methodology. Doug dives into why outbound sales motions have become so ineffective, the value of verticalization in competitive markets, and how much of an impact the "Thought-Leadershipization" of your Executive Team can have on your win rate.

Also, Craig is locked in a life-or-death struggle against the internet and Matt shares his personal insights on Nick Mehta and Doug’s fashion choices.

Takeaways:

  • Outbound sales reps need to earn the right to have a conversation with buyers before they share more about who they are and what they do. Sellers need to show buyers that they know them and understand the problems they’re facing, more so than the product solutions and features the buyer thinks they need.
  • The core idea of Hypothesis Selling is for sellers to communicate that they understand the problems a buyer is facing by providing them with a hunch or a hypothesis of what the seller thinks the buyer’s world might be like.

Chapters:

  • 00:00 Triassic Tattoos
  • 02:44 Introducing Doug Landis: A Beacon of Sales Wisdom
  • 05:36 How has the GTM Playbook Changed in the Past 4 years
  • 11:34 The Art of Outbound: Rethinking Sales Strategies
  • 25:16 Unlocking the Secrets of Killer Products
  • 26:16 Survival Tips for Inferior Products
  • 27:37 The Art of Execution: From Market Demand to Customer Conversations
  • 34:24 The Impact of the "Thought-Leadershipization" of your Executive Team
  • 41:49 Who’s the Best-dressed in B2B?

Quote of the Show:

  • “If you're going to earn the right to actually share more about who you are and what you do, then you've got to build that.” - Doug Landis

Sponsor:

Connect with Doug Landis:

Shoutouts:

Welcome back to The Transaction! In our second episode, you’ll hear from a truly classic Founder who is full of marketing ideas that are disrupting the status quo of B2B marketing.

Mac Reddin is the Founder and El Rey de Dinos at Commsor, the company behind both Matcha and Bronto. Mac joins co-hosts Craig Rosenberg and Matt Amundson to save go-to-market teams from the 99% of what they do that is wrong or misguided. Mac dives into his Vibe-First Marketing approach, how a few hundred chicken wings upended event marketing, and what it takes to inundate LinkedIn without spending a dime.

Also, Craig complains about New York City winter weather and Matt divulges his European shoe size.

Takeaways:

  • Marketers shouldn’t judge an idea solely based on how measurable it is.
  • The bar for a campaign working and being seen as creative and new is incredibly low in B2B. Come up with an idea that actually breaks through the noise of sameness from your competitors and then stick to it.
  • Build strong relations with your customers, prospects, and audience by creating something they want to be a part of.
  • When Founders are active on social and leading from the front, it allows people to connect closer with them and the company, making the marketing team’s (and everyone else’s) jobs much easier.

Chapters:

  • 00:00 - Craig Complains about the Cold
  • 01:48 - Introducing Special Guest Mac Reddin!
  • 04:03 - What GTM Teams are Doing Wrong & Vibe-First Marketing
  • 09:05 - The Chicken Wing Example of a Vibe-First Marketing Approach
  • 16:39 - How Commsor’s Booth Compares to Traditional Event Marketing
  • 20:40 - Mac’s B2C Sources of Inspiration
  • 24:49 - How to Create an Influencer Campaign to Conquer LinkedIn
  • 31:29 - The Impact of Consistently Building Strong Relationships In Your Market
  • 34:46 - How B2B Marketers Should Think About Video Content
  • 38:22 - Founders That are Active on Social Media are a Secret Weapon
  • 43:46 - Being Intentional and Consistent with LinkedIn are Key

Quote of the Show:

  • “When I think about marketing ideas and when our team thinks about them, we tend to think from a vibe-first mentality. We think more from the perspective of how are people going to feel about this?” - Mac Reddin

Sponsor:

Connect with Mac:

Shoutouts:

Follow the Show:

Ways to Tune In:

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Welcome to the first full episode of The Transaction! We’re kicking things off right with an amazing guest who is known for her time as President and COO of Gong, and as Executive Vice President, Sales at Tableau. Kelly Breslin Wright is now the Founder of Culture Driven Sales and an Adjunct professor at the University of Washington.

Kelly joins Host Craig Rosenberg for a fantastic conversation about the shift from traditional sales methods towards a 'Culture Driven Sales' approach, how a company’s mission and values are crucial for internal alignment, and how companies can actually be data-driven in their decision-making processes.

Chapters:

  • 00:00 - Welcome to the Show & Recapping Matt’s California Road Trip
  • 07:54 - Introducing Special Guest Kelly Wright
  • 11:36 - Most Company Leaders are NOT Aligned
  • 24:34 - People, People, People: The Core of Successful Companies
  • 33:32 - Simplifying Business: The Power of Keeping It Simple
  • 34:27 - The Impact of Culture on Sales and Customer Relationships
  • 35:54 - Navigating the Challenges of High Performers with Poor Cultural Fit
  • 39:16 - Embracing Data-Driven Strategies in Go-to-Market Teams
  • 49:39 - The Basis of Culture Driven Sales

Quote of the Show:

  • “Culture Driven Sales is about emotionally connecting with other human beings so that you can understand what their need is and they're more likely to buy because you're actually speaking on a more emotional level than on a transactional, tactical level.” - Kelly Wright

Sponsor:

Connect with Kelly Wright:

Shoutouts:

Words Coined This Episode:

  • Unactionable - Craig Rosenberg

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What does an opportunity mean to you? Would the rest of your company give the same answer? Probably not. But not to fear, GTM leader, because Tricia Gellman, the CMO of Box joins hosts Matt Amundson and Craig Rosenberg to explain how to fix the cracks between sales and marketing. Tricia outlines the importance of having shared goals across sales and marketing teams, why defining terms clearly is so critical, and what it’s like for those selling AI tools to B2B buyers.

Also, Craig recounts his time spent hanging out with reps at Dreamforce and Matt gushes about the events TOPO used to run.

Critical Takeaways

  • A crucial component in driving sales and marketing alignment is using the same metrics and dashboards to accomplish shared goals. Consistency and agreement on these metrics will help streamline the goal-setting process, reduce friction, and ensure everyone is working towards the same company objectives.
  • Clearly define what constitutes an opportunity and different stages within the pipeline. Aligning these definitions across marketing and sales will prevent discrepancies and confusion, leading to more accurate performance tracking and reporting.
  • Invest in brand building. A strong brand is essential for long-term success and helps in making conversations happen at the C-suite level. This investment continues to pay off by fostering word-of-mouth recommendations and creating a lasting impression in the minds of decision-makers.
  • Building a community, especially around high-level executives and key decision-makers, can significantly enhance your brand's reach and credibility. Hosting events and creating opportunities for peer networking add tremendous value and deepen customer loyalty.

Sponsored Segment

This episode is presented by Ringmaster Conversational Marketing, the go-to branded podcast team. To discover how your company can leverage B2B podcasts to deliver outsized ROI, visit ringmaster.com.

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

Chapters

00:00 Tricia's Italy Trip & Career Advice

03:08 Overcoming the Challenges of a CMO

04:51 Managing Pipeline in the Current Environment

08:56 How to Align Marketing and Sales Teams

23:26 Aligning Incentives Across Teams

24:01 Defining Opportunities and Meetings

25:18 Adapting to AI in Sales

27:13 Transitioning to a New CMO Role

32:22 Building Community and Product Alignment

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

Epic Quotes

  • “Saying you can't do it because you don't have the data is just a cop out.” - Tricia Gellman
  • “Everybody works to their goals. Whatever the incentive is, that's what people work towards.” - Tricia Gellman
  • “One of the key roles of leadership across sales and marketing is really being clear on who are we going after? Why are we going after it? And then, how are we going to go after it?” - Tricia Gellman

Connect with Tricia Gellman

Shoutouts

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

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How do you steal the spotlight from Marc Benioff at Dreamforce? By hiring a Benioff impersonator. Yes, Kyle Porter and the Salesloft team ACTUALLY did that. But they didn’t stop there...

Joining co-hosts Matt Amundson and Craig Rosenberg to chat about the amazing stunts pulled in the early days of Salesloft and how to build a healthy company culture is Kyle Porter himself, the Founder and Board Chair of Salesloft. Beyond bringing a Benioff doppelganger to Dreamforce, Kyle shares some brilliant plays his team used to drive brand awareness and become the biggest story at their competitor’s conference. Kyle also dives into how he built a loving culture within Salesloft and how that loving culture was extended to and felt by their customers.

Also, Craig provides a gripping tale about his experience with an elevator and Matt sets the record straight on whether a presentation he gave was sweaty or swear-y.

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

Critical Takeaways

  • When you really love your customers and they can actually feel that love, they are willing to go to bat for you and your company. Because Matt felt that Kyle loved him-as a customer-he would defend and promote Salesloft when others were defending or promoting a competitor.
  • Building a strong company culture is more important than ever. It should be built on love–in a platonic way–for the members of your organization. A healthy organizational culture translates to better team dynamics, productivity, and ultimately, better customer interactions and satisfaction.
  • Dare to be different, especially when it comes to events. People will only really remember 1-2 things from an event, so it’s critical to make that shortlist. A bigger booth doesn’t necessarily make you more memorable. Most event booths zig, so find a way to zag, even if it means doing something other than a booth (Sorry if that one hit too close to home).

Sponsored Segment

This episode is presented by Ringmaster Conversational Marketing, the go-to branded podcast team. To discover how your company can leverage B2B podcasts to deliver outsized ROI, visit ringmaster.com.

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

Chapters

00:00 Introducing Kyle Porter!

08:25 Awesome SaaS Stunts from the Salesloft Team

26:00 The Importance of Organizational Culture and Leadership

30:18 Loving Your Customers

32:54 Building a Community & Leveraging Customer Advocacy

44:28 How to Build a GREAT Sales Deck and Engage with Key Decision Makers

50:36 The Impact of Kyle’s Brand as a Founder

Epic Quotes

  • “We're going to continually love and serve our customers and our people better than anyone else. And when you care more than anyone else, you're going to win ultimately.” - Kyle Porter
  • “When a customer bought SalesLoft, I had the mentality that they had just saved my life and I was going to treat them as such” - Kyle Porter
  • “Taking care of your employees Actually helps you take care of your customers” - Matt Amundson

Connect with Kyle

Shoutouts

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Every Founder has a story to tell and by telling that story in a compelling way, they can give their company an outsized advantage and the leg up they need in order to grow.

The founder of multiple companies and a veritable thought leader in his own right, Scott Albro, joins Hosts Craig Rosenberg and Matt Amundson, for a rollicking romp through the big AI questions now getting asked, the fundamentals for building a successful founder brand, and how to create high-quality content that is worthy of your buyers’ time and attention.

The crew dives into an intriguing debate over whether AI Co-Pilots or multitudinous AI Agents will win out in the future as AI is integrated into more go-to-market jobs and processes. Scott shares his three-part framework for helping founders tell compelling stories and everyone, including Sam, shares their favorite examples of successful founder brands.

Also, Craig is complimented on his militaristic sleeping abilities and Matt begins the long journey to recovery by admitting to his reprehensible road rage.

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

Critical Takeaways

  • For the love of god, please prioritize quality ahead of quantity. For example, your sales and marketing teams should focus on producing high-quality content and interactions that resonate with target customers, rather than just attempting to increase touchpoints indiscriminately. Just because you can, definitely does not mean that you should (You should have learned this from Jurassic Park).
  • Publishing quality content consistently is critical for anyone building a following on social media platforms. A good cadence for growth on most platforms is posting three times a week. This helps you stay on top of your audience’s feed and top of mind for buyers.
  • Create content in the medium and format that is most comfortable for you. Whether it’s writing, video, or audio, the point is to not make the content production process more painful for you.
  • The three types of stories that Scott recommends founders telling are: 1. How well you understand customer pain points, their priorities, and how to solve their problem. 2. How the market will change and how to navigate it. 3. Your personal journey.
  • Using AI to write crappy, clearly fake comments on LinkedIn posts from contacts within your target accounts will cause major damage to your brand. Automated comments on LinkedIn are extremely easy to spot and

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 - Walking Through a Winter Wonderland
03:23 - Introducing Scott Albro
10:51 - AI Adoption is Taking Us Down the Wrong Path
13:20 - The Important AI Debates Happening Today
16:03 - Where AI Agents & Co-Pilots Fit into Go-To-Market
27:20 - Using AI on LinkedIn
37:47 - Creating Quality Content
47:29 - Scott's Framework for Which Story Founders Want To Tell
50:22 - Examples of The Best Founder Brands
57:21 - The Impact of Scott's Shoe Game on the Market

Epic Quotes

  • “ AI feels like a market where we are going to experiment our way into the right use cases. Because they're not obvious” - Scott Albro
  • “Every founder has a story to tell. Otherwise they wouldn't have started a company.” - Scott Albro

Connect with Scott Albro

Shoutouts

Today’s episode is a real treat because we have multiple amazing guests joining Craig Rosenberg and Matt Amundson for a deep dive into the state of MarTech today and how to think about generative AI within the larger AI conversation. Scott Brinker & Esteban Kolsky are two of the foremost thinkers and analysts in the B2B world and are here together to volley high-value concepts and insights. Scott, Esteban, and Craig dissect the challenges and potentials of generative AI (Gen AI), the proliferation of MarTech vendors, and the critical need for democratized data in use versus data in storage.

Also, Matt shares why he thinks Mr. and Mrs. Smith has the best season finale in tv history and Craig examines his use of the word “gangster”.

Takeaways:

  • Build software solutions with integration in mind.
  • Data in storage is vastly different from data in use. The value of data comes not just from collecting it but from actively applying it to solve problems and guide decisions. Make your data actionable.

Chapters:

  • 00:00 - Quick Recap of True Detective and What Craig Learned
  • 10:07 - Introducing the Dynamic Duo: Scott Brinker & Esteban Kolsky
  • 14:17 - The Trouble with Defining the Value of Marketing Properly
  • 21:57 - Comparing Marketers’ Relationship to MarTech and Marketing Agencies
  • 28:54 - Barriers to Entry for SaaS Vendors Have Dropped Drastically
  • 37:57 - A Surprisingly Apt Football Analogy for Thinking About AI & Vendors
  • 45:27 - How Generative AI is Democratizing Access to Data
  • 56:37 - Liquid Death Auctioning Off Ad Space on Ebay

Quote of the Show:

  • “You need to treat integration as a first-class capability because if people can't integrate this stuff with the rest of their stack, they're not going get the value out of you.” - Scott Brinker
  • “Once you understand that computers make based on one and zeros that are stored, the world is a lot simpler to go through. Then it's just go play poker.” - Esteban Kolsky

Sponsor:

Connect with Scott Brinker:

Connect with Esteban Kolsky:

Shoutouts:

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