
The Transaction
Matt Amundson & Craig Rosenberg

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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.

Empowering The Agile, Tech-Enabled Salesforce with Mary Shea - The Transaction - Ep #6
The Transaction
04/18/24 • 50 min
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:
- Ringmaster Conversational Marketing - The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/
Connect with Mary:
- LinkedIn: https://www.linkedin.com/in/maryshea/
Shoutouts:
- Andy Hoar: https://www.linkedin.com/in/andyhoar/
- Testbox: https://www.testbox.com/
- Outreach: https://www.outreach.io/
- Gong: https://www.gong.io/
- Salesloft: https://www.salesloft.com/
- Apollo: https://www.apollo.io/
- Drift, a Salesloft Company: https://www.drift.com/
- Seismic: https://seismic.com/
- Mediafly: https://www.mediafly.com/
Follow the Show:
- Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
- Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/
- The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/
- The Transaction Website: https://thetransactionpod.com/
- Substack: https://thetransaction.substack.com/
Ways to Tune In:
- Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz
- Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309
YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1

3 Listeners

Decoding The CRM and Database Infrastructures with Nicolas de Kouchkovsky - The Transaction - Ep #7
The Transaction
04/25/24 • 52 min
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:
- Ringmaster Conversational Marketing - The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/
Connect with Nicolas:
- LinkedIn: https://www.linkedin.com/in/nicolask3/
- CaCube Consulting Website: https://www.cacubeconsulting.com/
Shoutouts:
- Scott Brinker: https://www.linkedin.com/in/sjbrinker/
- Fivetran: https://www.fivetran.com/
- Airbyte: https://airbyte.com/
- Clay: https://www.my-clay.com/
- 6Sense: https://6sense.com/
- Demandbase: https://www.demandbase.com/
- Madkudu: https://www.madkudu.com/
- Bombora: https://bombora.com/
- Regie.ai: https://www.regie.ai/
Follow the Show:
- Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
- Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/
- The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/
- The Transaction Website: https://thetransactionpod.com/
- Substack: https://thetransaction.substack.com/
Ways to Tune In:

3 Listeners

03/21/24 • 49 min
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:
- Ringmaster Conversational Marketing - The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/
Connect with Mac:
- LinkedIn: https://www.linkedin.com/in/mac-reddin/
- Commsor Website: https://www.commsor.com/
- Matcha.so Website: https://matcha.so/
- Bronto Website: https://www.bronto.co/
- YouTube: https://www.youtube.com/@Commsor/featured
Shoutouts:
- Sam Guertin: https://www.linkedin.com/in/sam-guertin/
- MSCHF: https://mschf.com/
- Most viewed videos on YouTube: https://en.wikipedia.org/wiki/List_of_most-viewed_YouTube_videos
Follow the Show:
- Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
- Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/
- The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/
- The Transaction Website: https://thetransactionpod.com/
- Substack: https://thetransaction.substack.com/
Ways to Tune In:

3 Listeners
1 Comment
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04/11/24 • 57 min
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:
- Ringmaster Conversational Marketing - The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/
Connect with Chris Orlob:
- LinkedIn: https://www.linkedin.com/in/chrisorlob/
- pclub.io Website: https://www.pclub.io/
- Twitter: https://twitter.com/Chris_Orlob
Shoutouts:
- Kelly Wright: https://www.linkedin.com/in/kellybreslinwright/
- Kelly Wright’s Episode of The Transaction: https://thetransaction.substack.com/p/people-people-people-kelly-wright?r=3iae7z
- Krysten Conner: https://www.linkedin.com/in/krystenconner/
- Ted Purcell: https://www.linkedin.com/in/tedpurcell/
- Ted Purcell’s Podcast Episode: https://www.gtmunfiltered.com/episodes/building-trust-through-grit-based-authenticity-ted-purcell-gtm-unfiltered-episode-006
Follow the Show:
- Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
- Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/
- The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/
- The Transaction Website: https://thetransactionpod.com/
- Substack: https://thetransaction.substack.com/
Ways to Tune In:

3 Listeners

05/09/24 • 48 min
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:
- Ringmaster Conversational Marketing - The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/
Connect with Doug Landis:
- LinkedIn: https://www.linkedin.com/in/douglandis/
- DL Advisory Website: https://www.douglandis.com/
Shoutouts:
- Maria Pergolino: https://www.linkedin.com/in/mariapergolino/
- Arc'teryx logo tattoo: https://www.tiktok.com/@kjadeg/video/7337453935013252394
- Arc'teryx response: https://www.tiktok.com/@kjadeg/video/7345316691762711851
- Lavender: https://www.lavender.ai/
- Norwest Ventures: https://www.nvp.com/
- Doug’s post about Norwest Ventures report: https://www.linkedin.com/posts/douglandis_kudos-to-norwest-venture-partners-for-this-activity-7179189994635370496-LULM?utm_source=share&utm_medium=member_desktop
- Kyle Coleman: https://www.linkedin.com/in/kyletcoleman/
- Copy.ai: https://www.copy.ai/
- Infor: https://www.infor.com/
- Chris Ball: https://www.linkedin.com/in/chris-ball-010/
- Veeva: https://www.veeva.com/
- Peter Gassner: https://www.linkedin.com/in/pgassner/
- Nick Mehta: https://www.linkedin.com/in/nickmehta/
- Gainsight: https://www.gainsight.com/
- Amy Chang: https://www.linkedin.com/in/changamy/
- John Barrows: https://www.linkedin.com/in/johnbarrows/
- John Barrows’ episode of The Transaction:
3 Listeners

03/14/24 • 60 min
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:
- Ringmaster Conversational Marketing - The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/
Connect with Kelly Wright:
- LinkedIn: https://www.linkedin.com/in/kellybreslinwright/
- Culture Driven Sales Website: https://culturedrivensales.com/
- University of Washington Foster School of Business Website: https://foster.uw.edu/faculty-research/directory/kelly-wright/
Shoutouts:
- Barbareño: https://www.barbareno.com/
- Sam Guertin: https://www.linkedin.com/in/sam-guertin/
- Casey Cheshire: https://www.linkedin.com/in/caseycheshire/
- Lena Waters: https://www.linkedin.com/in/lenawaters/
- Dannie Herzberg: https://www.linkedin.com/in/dannieherzberg/
- Olivia Nottebohm: https://www.linkedin.com/in/olivia-nottebohm-7095b0/
- Panel Mentioned by Craig: https://afterparty.gong.io/public/76/%23Celebrate-70ab8437/296a7c22
Words Coined This Episode:
- Unactionable - Craig Rosenberg
Follow the Show:
- Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
- Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/
- The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/
- The Transaction Website: https://thetransactionpod.com/
- Substack: https://thetransaction.substack.com/
Ways to Tune In:

3 Listeners

02/27/25 • 57 min
There are more people than ever involved in deals on both the vendor side and customer side, and it’s having a massively negative impact on B2B growth.
Nick Toman is the Chief Product and Transformation Officer at SBI (Sales Benchmark Index) and is the third and final co-author of The Challenger Sale we’ve had on the show. Nick brings some amazing new sales and business research to dive into with co-hosts Matt Amundson and Craig Rosenberg. Nick unveils the effect that having more sellers involved has on win rates, the three behaviors of B2B salespeople that lead to the best commercial relationships, and why actions that seem like they would slow down deals are actually the key to closing them faster. Matt sparks an interesting discussion around sales compensation and the impact it has on both the behaviors of B2B sellers and the growth of the company on the whole. Toward the end, Nick teases his new concept of 'Headway Selling,' which focuses on actually helping customers reach their goals rather than simply selling them as much useless crap as possible.
Also, Craig recounts his childhood trauma of growing up a Dodgers fan in San Fransisco, Matt practices to be a court stenographer, and Sam the Producer confesses to an affinity for gnomes (?).
Join our Newsletter: https://thetransaction.substack.com/
Critical Takeaways
- Not only have buying groups grown immensely, but the number of people working on deals with those buying groups has also exploded. There are now an average of 12 people in buying groups and 5 people involved with the sale from the vendor side. This has led to a spike in confusion for buyers and a sharp decline in win rates for salespeople.
- The role of CSMs (Customer Success Managers) has devolved to have an extremely broad remit that is too big for them to actually deliver on effectively. In an ideal world, the CSM role should be to use very clear signals to identify customers who are struggling with adoption or retention issues and help them solve those issues. As it stands, many CSMs provide ongoing services and end up competing with account managers to land expansion and renewal opportunities. The competition on its own is one thing, but once the business is compensating both the CSM and the AM, there’s an issue with cost and efficiency.
- B2B sales reps need to focus on deeply understanding and aligning with customer initiatives. Sellers should be thinking about how they can help customers grow in their own businesses and avoid roadblocks. Gaining this deeper understanding of customer needs drastically shortens sales cycles and increases deal sizes.
- There are 4 main archetypes of behavior for people in commercial roles: 1. Narrowing- Closing early, Closing often. 2. Provoking - Provocative insights to redirect customer thinking (AKA: Challenger). 3. Translating - Detail & data-oriented to help customers understand impact. 4. Anticipating - Help customers think through the process and future challenges.
- Of those 4 archetypes, the two that perform best in sales are Translating and Anticipating. The research showed that sellers exhibiting those behaviors actually closed deals more quickly and for more money than sellers using the Narrowing or Provoking behaviors.
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 Coming Up in this Episode...
00:40 Will the Real Nick Toman Please Stand Up
01:53 Introducing Nick Toman, Co-Author of The Challenger Sale
03:09 The Impact of The Challenger Sale in B2B Sales
13:55 Commercial Efficiency is Crippling B2B SaaS Growth
21:22 Is Sales Commision Getting out of hand for B2B Companies?
28:22 Why Don't Buyers Want to Talk to Sellers Anymore?
31:05 Key Behaviors for Successful Commercial Relationships
33:53 Why Starting Fast Is So Critical for Sales Success All Year Long
36:27 Strategies for Effective Sales Execution to Start the Fiscal Year Strong
41:08 Understanding The Four Commercial Role Archetypes & Their Impact on Deal Velocity
48:54 Customer-Centric Selling and Trust Building
53:56 Headway Selling & Delivering Real Customer Success
Epic Quotes
- “ You’ve got to help the customer make headway and you don't want to make headwinds.” - Nick Toman
- “ Commercial efficiency- the yield on dollars spent in s...

2 Listeners

11/14/24 • 45 min
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
- LinkedIn: https://www.linkedin.com/in/gellmansfmarketing/
- Website: https://www.box.com/home
Shoutouts
- Mini Peiris: https://www.linkedin.com/in/mini8ture/
- Maria Pergolino: https://www.linkedin.com/in/mariapergolino/
- Sydney Sloan: https://www.linkedin.com/in/sydsloan/
- Ted Purcell: https://www.linkedin.com/in/tedpurcell/
- Latané Conant: https://www.linkedin.com/in/latane-conant/
Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

2 Listeners

01/30/25 • 60 min
When your buyer isn’t confident in the decision they’re making, they will choose not to decide. Meaning, that you’re not going to close that deal, which is a serious problem in B2B.
To help solve that problem, we’re thrilled to welcome Brent Adamson, the co-author of The Challenger Sale and renowned sales speaker, to the show. Brent joins hosts Matt Amundson and Craig Rosenberg to discuss the crucial sales topics in his new upcoming book, The Framemaking Sale. They get into the problem with value-selling, why sellers need to teach buyers how to buy with confidence, and where thought leadership is falling short in today’s environment.
Also, Craig pitches an idea for a radical new podcast and Matt cuts to the front of the line to call dibs.
Critical Takeaways
- Focus more on building customer confidence in their own decision-making abilities rather than just showcasing the value of your product. If customers are reluctant or unsure, they will likely delay or avoid purchasing altogether.
- Bring implementation and customer success representatives into pre-sale discussions. This helps reassure the customer that post-sale support will be robust and demonstrates your commitment to their success.
- Instead of just showcasing customer success stories, position them as a tool to show customers how to buy so that new customers understand the buying process and pitfalls to avoid. This gives prospects practical advice and increases their confidence in making a complex decision.
- Optimize your sales process to lose deals quickly. If a deal is likely to be lost, aim to lose early rather than late. This saves your sales team time, resources, and focus for more promising opportunities.
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 - Trailer
01:25 - Introducing Brent Adamson
03:51 - I’m Tired of these MFing Maggots on this MFing Plane
10:08 - The Impact of Buyers’ Low Confidence in Themselves
18:42 - Buyers Don’t Know How to Buy
23:44 - Implementing a Objectives, Tactics, Results Approach to Sales
30:49 - The Problem with Replicating Successful Sellers
36:26 - Thought Leadership & Content Marketing’s Role in Building Confidence
40:49 - How to Building Customer Confidence
45:16 - The Role of Founders in Sales
51:39 - Wrap Up
Sign up for our Newsletter: https://thetransaction.substack.com/
Epic Quotes
- “Solve for customer’s confidence in themselves” - Brent Adamson
- “ It's not that I'm selling badly, it's that customers are buying badly.” - Brent Adamson
Connect with
- LinkedIn: https://www.linkedin.com/in/brentadamson
- Website: https://www.brentadamson.net/
- A to B Insights Website: https://atobinsight.com/
- Maggots on a Plane Video: https://youtu.be/BFp30CkVcLo?si=aDSKIeQOTfyt9IZ5
Shoutouts
- Karl Schmidt: https://www.linkedin.com/in/karl-schmidt-q/
- Bryan Smith: https://www.linkedin.com/in/bryankeithsmith/
- Tyler Harnish: https://www.linkedin.com/in/tylerharnish/
- Marc Benioff: https://www.linkedin.com/in/marcbenioff/
- Sense-making for Sales in HBR: https://hbr.org/2022/01/sensemaking-for-sales
- Matt Dixon: https://www.linkedin.com/in/matthewxdixon/
- Stephen Powell: https://www.linkedin.com/in/stephen-powell-06996785/
- Kevin Hendrick: https://www.linkedin.com/in/kevinhendrick/
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Overcoming Epilepsy & How to Hire with Michael King - Ep. 46
The Transaction
03/17/25 • 56 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 Takeaways
- Ensure 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 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
02:58 Introducing Michael King
04:15 Michael's New Book & Incredible Personal Journey
09:29 Recruiting Career & Success Stories
18:54 Amazing Event Marketing Anecdotes
27:44 Falling in Love with a Brand
28:33 The Importance of Relevant Experience
33:55 Chasing Titles vs. Chasing Companies
39:14 The Value of Good Companies
49:03 Epilepsy Awareness and Personal Stories
Sign 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 King
Connect with Michael
- LinkedIn: 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
Shoutouts
- George Wallace
- Maria Pergolino
- Will Smith & DJ Jazzy Jeff Reunion at Everstring’s Pool Party: https://youtu.be/v6-QoeusjEs?si=2CynMyahkkqG1mT8
- Jessica Cross
- Stephanie
- Stacey Epstein
- David Mylam
- Dave Arnold
- Michael Lundgren
- Miles Kelly
- Rob Bernstein
- Udi Ledergor
- Russell Udy
- SuccessFactors
- Salesforce
- Broadvision
- Okta
- Coupa
- Siebel
- Gong
- Cresta
Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

2 Listeners
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FAQ
How many episodes does The Transaction have?
The Transaction currently has 50 episodes available.
What topics does The Transaction cover?
The podcast is about Marketing Podcast, B2B Sales, Tech, Venture Capital, Marketing, Founder, Cmo, Investing, Business Advice, Startup, Saas, Podcasts, Technology, Business Growth, Ceo, Sales, Sales Podcast, Business, B2B Marketing, B2B and Marketing Strategy.
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The episode title 'People, People, People! - Kelly Breslin Wright - The Transaction - Ep #1' is the most popular.
What is the average episode length on The Transaction?
The average episode length on The Transaction is 52 minutes.
How often are episodes of The Transaction released?
Episodes of The Transaction are typically released every 7 days.
When was the first episode of The Transaction?
The first episode of The Transaction was released on Mar 5, 2024.
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@samguertin
Apr 20
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