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.

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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

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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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When you can tell your story in a compelling, confident way, you can change the lens through which everyone views you, your accomplishments, and your potential.

Dia Bondi, a TEDx speaker, author of Ask Like An Auctioneer, and executive coach, joins Hosts Craig Rosenberg and Matt Amundson for an exceedingly energetic and entertaining conversation focused on communicating effectively as a leader. In between some fun tangents, they dig into how to uncover and craft your origin story to tell a more compelling narrative, why doing live demos on stage needs to go the way of the dodo, and how to raise more funding without a pitch deck. They also discuss their favorite examples of leaders who are actually doing this well and showing the world who they really are. Strap in for a fun and informative fifty-two minutes that every aspiring leader needs to hear (or watch if you’re on Spotify or YouTube).

Also, Matt mixes up 1960s movie characters named Felix and Craig channels his inner Sully as he desperately attempts to land multiple planes.

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Critical Takeaways

• When someone asks you who you are, don’t rifle through the bullets of your resume. Instead, tell them the narrative of your origin story. Include the core things that drive you, the context around why you set out to do X, and who you really are.
• Speaking on stage is too expensive for you to have a live demo of your product that doesn’t work. It’s much better to have a pre-recorded demo for your presentation and then give people an opportunity to interact with a live demo at your booth where things are lower stakes if the product fails.
• Founders need to realize when to hand off the tactical duties in their all-hands meetings, such as being the emcee or running a slide deck. Your team needs you to show up at the status that matches the role that people need you to play in the world.
• All-hands meetings are extremely expensive, especially the ones that are run poorly and time-intensive. You need to allocate your team’s time carefully based on what is most important to the company’s mission, so make sure not to squander that precious time.
• Being a compelling communicator is not about being perfectly polished, it’s about staying true to yourself and adapting your natural approach to each context while maintaining authenticity.

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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

00:20 - Craig comes Straight Outta Compton

00:58 - Fun Facts about Dia Bondi, Matt, & Softball

04:09 - Introducing Dia Bondi

08:20 - The Impact of Establishing Your Voice

12:13 - What is Founder Unrest & When Does It Show Up?

15:19 - How Founders can Find Their Own Voice & Unlock Their Origin Story

20:42 - Why Understanding How to Tell Your Origin Story Matters

31:12 - Dump the Live Demos from your Presentations

33:15 - Wait, How Expensive are All-Hands Meetings?

38:20 - Two Big Misconceptions about Communication

43:44 -  Examples of Leaders with Great Perspectives & Well-Developed Voices

50:04 - Craig Compliments Sam for Displaying Basic Competence

50:24 - Wrapping Up

Epic Quotes

• “ Founders are always going into conversations that are bigger than their britches. That's kind of like a job requirement.” - Dia Bondi
• “ To win and to differentiate today, we need the founder to reach trusted superstar status as fast as possible.” - Craig Rosenberg
• “ I think of founder voice as something you lend to your venture.” - Dia Bondi

Connect with Dia

• LinkedIn: https://www.linkedin.com/in/dia-bondi/ 
• Website: https://www.diabondi.com/ 
• Dia’s TED Talk: https://youtu.be/mFtHKTgyjyU?si=oElL9kWENAiSMary 
• Ask Like An Auctioneer (Book): https://www.asklikeanauctioneer.com/ 
• Dia’s Resource Library: https://www.diabondi.com/resources 

New Terms: 

• Buttwing (v): To guesstimate. See Also: Ballpark

Shoutouts

• Claire Sua-Amundson: https://uclabruins.com/news/2013/4/17/208207255 
• Claire Pitching to Dan Le Batard: https://youtu.be/o-HM5Sm5omA?si=3yzu1TtT_tD5mUyq 
• Funny Article about Claire and Matt: https://vault.si.com/vault/2005/06/06/-hitting-the-big-time 
• Dan Le Batard: https://lebatardaf.com/ 
• The Odd Couple (1970-1975)
• Howard Schultz: https://www.linkedin.com/in/howardschultz/ 
• Howard Schultz Interview on Acquired: https://youtu.be/A0fvX-wV70Y?si=-Ljn1jqTYP5aGEaR 
• Starbucks: https://www.starbucks.com/   
• Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ 
• Jensen Huang Interview on Acquired: https://youtu.be/y6NfxiemvHg?si=bfv8w-1wgTZk5l6A 
• Nvidia: https://www.nvidia.com/en-us/ 
• Nick Mehta: https://www.linkedin.com/in/nickmehta/ 
• David Solomon: https://www.linkedin.com/in/david-m-solomon/ 

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

Justin Gray, author of the brand new The Go-to-Market Cheat Code and Co-Founder of In Revenue Capital joins Hosts Matt Amundson and Craig Rosenberg to share how to build more effective and efficient B2B partnership programs, why nothing seems to be working in marketing, and his cheat codes to go-to-market success in B2B. Justin explains how and why LeadMD evolved from being a competitor to building an extremely strong partnership with Marketo. There’s also a great discussion about what VCs and other investors look for in founders when investing in startups and how this has changed in recent history.

Also, Matt vehemently opposes accusations of being hyperbolic and Craig recants on one of his ill-concieved New Years resolutions.

Critical Takeaways

• The success of any partner progam depends first and foremost on executive alignment. Without buy-in from leadership, 99% of B2B partnerships will fail.
• No matter how good your content may be, you still have to earn the right and access to get your content in front of your target audience by building strong relationships.
• Stop looking for copy and paste playbooks to use that are being used by everyone else in the market. If you don’t you’ll just be adding your content and brand to the endless pile of lifeless, gray ooze of things that get ignored. Take a risk and you’ll at least have a chance of sticking out.
• Any partner motion begins with building a relationship with one person. Find the right people to focus on and start one at a time. This is a much quicker way to build real relationships and trust than trying to boil the ocean and make a play for everyone at once.

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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 Introducing Justin Gray

00:50 The Origin Story of LeadMD and how they Partnered with Marketo

09:55 The Go-To-Market Cheat Code Book

16:47 Craig makes fun of Justin’s Office

18:12 Lessons on Relationships from The Wild West of the Payment Processing Industry

30:26 The Cycle of Innovation and Imitation

32:09 The Importance of Knowing Your Buyer

40:34 What Venture Capital looks for in Founders

46:50 Building Effective Partnerships

1:05:02 18th Book Plug of the Episode

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

Epic Quotes

• “ What's working is what has always worked which is trusted relationships” - Justin Gray
• “Innovators look for ideas” - Craig Rosenberg

Connect with Justin

• LinkedIn: https://www.linkedin.com/in/inrevenue/ 
• The Go-to-Market Cheat Code (Book): https://inrevenue.capital/cheat-code/ 
• Order The Go-to-Market Cheat Code on Amazon: https://amzn.to/4hjtrbA 
• In Revenue Capital Website: https://inrevenue.capital/ 
• The GTM Cheat Code (Podcast): https://inrevenue.capital/insights/?article_category=podcast 

Shoutouts

• Essentials/Fear of God Clothing: https://fearofgod.com/ 
• Focus
• MAAS Impact
• Chris Selland: https://www.linkedin.com/in/cselland/ 
• LeadMD
• Marketo
• Bill Binch: https://www.linkedin.com/in/bill-binch-302a4a2/ 
• Margaret Hoogerbeets: https://www.linkedin.com/in/mhoogerbeets/ 
• Amy Guarino: https://www.linkedin.com/in/amyguarino/ 
• Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ 
• Scottsdale Princess: https://www.scottsdaleprincess.com/ 
• Josh Wagner: https://www.linkedin.com/in/joshwagneraz/ 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 
• Jon Miller’s Post about the Tragedy of the Commons in Marketing: https://www.linkedin.com/posts/jonmiller2_mpb2b-b2bmarketing-marketingautomation-activity-7262460572032483328-hs0J? 
• Dirty Money, Season 1, Episode 2: https://www.netflix.com/us/title/80118100?s=i&trkid=258593161&vlang=en 
• Bessemer: https://www.bvp.com 
• Nick Mehta: https://www.linkedin.com/in/nickmehta/ 
• Marc Beniof: https://www.linkedin.com/in/marcbenioff/ 
• Founder’s Fund: https://foundersfund.com/ 
• Asher Mathew: https://www.linkedin.com/in/ashermathew/
• AWS Marketplace: https://aws.amazon.com/marketplace 

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

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.

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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

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

Shoutouts

• Chris Orlob: https://www.linkedin.com/in/chrisorlob/ 
• Chris Orlob’s Episode of The Transaction: https://substack.com/@thetransaction/note/p-143505807?utm_source=notes-share-action&r=3iae7z
• Matt Dixon: https://www.linkedin.com/in/mattdixon/ 
• Matt Dixon’s Episode of The Transaction: https://substack.com/@thetransaction/note/p-153859244?utm_source=notes-share-action&r=3iae7z
• David Politis: https://www.linkedin.com/in/davidpolitis/ 
• David Politis’ Episode of The Transaction: https://substack.com/@thetransaction/note/p-152597131?utm_source=notes-share-action&r=3iae7z
• John M. Jack: https://www.linkedin.com/in/johnmjack/ 
• Bland.ai: https://www.bland.ai/ 
• Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ 
• Dan Gottlieb’s episode of The Transaction: https://substack.com/@thetransaction/note/p-149757433?utm_source=notes-share-action&r=3iae7z
• Gartner: https://www.gartner.com/en 
• AI Adoption Study from Scale Venture Partners: https://www.scalevp.com/insights/ai-gtm-flash-survey-how-marketing-teams-are-actually-using-ai/ 
• Regie.ai: https://www.regie.ai/ 
• Outreach: https://www.outreach.io/ 
• Salesloft: https://www.salesloft.com/  
• Srinath Sridhar: https://www.linkedin.com/in/sridharsrinath/ 
• Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ 
• Marc Beniof: https://www.linkedin.com/in/marcbenioff/ 
• Tobias Lütke: https://www.linkedin.com/in/tobiaslutke/ 
• Shopify: https://www.shopify.com/ 
• ServiceTitan: https://www.servicetitan.com/ 
• Adam Robinson: https://www.linkedin.com/in/retentionadam/ 
• RB2B: https://www.rb2b.com/ 
• Nick Mehta: https://www.linkedin.com/in/nickmehta/ 

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

What is your GTM strategy built on? The cool new motion that's popular this minute? Tons of research on users? Well, it should be built from a blueprint and this guest just so happens to know how to create said blueprint. 

Adam B. Needles, the CEO of ANNUITAS, joins Craig Rosenberg and Matt Amundson for a barn burner of an episode that starts off with Adam’s seriously spicy take that the CMO’s role is a major part of the problem in the current B2B buying experience (Sounds like someone got into the Commsor hot sauces). After unpacking that hot tamale, Adam shares some great insights on the three parts to setting up and monitoring your Go-To-Market Blueprint, why you need to educate your board on how you go to market, and what buyers actually want from sellers during their buying journey. As if that wasn’t enough to include in this edition, Adam also drops a great nugget that AI can’t cover up your poor GTM Strategy.

Pretty sure the B. in Adam’s name stands for B2B Badass or something like that based on this episode. (Yes, that was corny and stupid and yes, a human, albeit not a very bright one, wrote that)

Also, Craig reminisces about his viral, rebellious past and Matt sits in a corner and cries at the downfall of his fiefdom.

Critical Takeaways

• The three core components of a go-to-market blueprint are understanding the buyer's journey, identifying all relevant decision-making stakeholders, and grasping their content consumption habits. This helps in synchronizing b2b marketing and sales efforts to ensure value-added interactions at every touchpoint.
• Every b2b marketing touchpoint should focus on adding value to the prospect's journey. That means every email, meeting, and piece of content prospects receive serves a purpose and helps them arrive at a quality decision faster.
• Don’t treat your go-to-market plan as if it’s set in stone. You should regularly meet with crossfunctional leaders to review the gtm blueprint, examine your performance against that blueprint, and update your go to market strategy based on new data and insights. 

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 - Freeing The Funnelholic

07:18 - The Problematic Role of the Chief Marketing Officer for B2B companies

20:52 - Creating a Value-Added Demand Motion for Buyers

34:11 - Building Your Go-To-Market Blueprint

40:47 - How to Get Your Board… On Board

49:53 - Daring to Peek Outside of the Tech Industry

56:17 - Your B2B Go-To-Market Playbook Needs a Playbook

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

Epic Quotes

• “ I don't think that AI is the solution to your bad go to market.” - Adam B. Needles
• “It's not about funnel management. It's really about just understanding where someone is in the journey.” - Adam B. Needles
• “If you don't have a clear sense of who owns what by stage, then nobody owns it.” - Adam B. Needles
• “ The new playbook is to have a playbook.” - Matt Amundson
• “ We talked about the CEO and COO, actually, now, the biggest education point for this change is board level.” - Craig Rosenberg

Connect with Adam

• LinkedIn: https://www.linkedin.com/in/abneedles/ 
• Website: https://www.annuitas.com/ 

Shoutouts

• Carlos Hidalgo: https://www.linkedin.com/in/carlosahidalgo/ 
• Jason Stewart: https://www.linkedin.com/in/jasonhstewart/ 
• Monotype
• Ninan Chacko: https://www.linkedin.com/in/ninan-chacko-54b527/ 
• Bob Seiler: https://www.linkedin.com/in/robertjseiler/ 
• Schneider Electric
• Procter and Gamble
• QA Symphony
• Forrester
• Gartner
• Evan Kent: https://www.linkedin.com/in/evankent/ 
• Salesloft
• Outreach
• HubSpot

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

If people are the ones buying software, then it’s probably important that your brand appeals to those people.

Fresh off a successful Dreamforce, Mini Peiris, the Chief Market Officer of Nintex, joins co-hosts Craig Rosenberg and Matt Amundson for an examination of how a brand should make buyers feel about themselves, the problems they face, and the solution provided. Mini also gets into when is the best time to ask customers for referrals, why playing nice with sales is key to being a successful Chief Marketing Officer, and how to reinforce a brand internally so that every customer touchpoint and interaction feels right. In a seeming first for the show, the conversation takes us past the point of transaction to look at the CMO’s role in the customer’s post-sale experience.

Also, Craig reveals his favorite source of apple fritters and Matt says something that is very succinct and to the point.

Critical Takeaways

• Even though you’re in B2B, it's still humans making the purchasing decisions. Focus on the people behind the accounts, the problems they face, and what their goals are to create more impactful B2B marketing messaging.
• Marketing’s job isn’t over when the customer signs on the line which is dotted. It’s crucial to continue engaging with customers post-transaction to ensure they derive value from your product and can become powerful and vocal advocates of your brand.
• The CEO is critical in developing and or pivoting the internal brand and culture of a company. Understanding them and getting their buy in and support is step number one for any Chief Marketing Officer looking to establish or adjust their company's brand.
• Great B2B marketing and storytelling can gloss over a product’s inferiorities and position a brand as the category leader. If you can articulate the customers’ problem and your solution better than your competitors, your brand will win, giving you time and resources to then shore up product deficiencies. 

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 - Live from San Fran, It’s Matturday Night Live

04:10 - What Makes a Great CMO and B2B marketing leader

07:34 - Don’t Forget that People Buy Software in B2B

13:38 - How Mini Built a Customer Community with Donuts

18:57 - Developing Your B2B Brand’s Core Identity

21:59 - The CEO’s Influence on Brand & Culture 

27:19 - Examples of Great B2B Brands

32:34 - The CMO’s Role in The Post-Transaction Customer Experience

40:19 - How Execs Buy B2B Software Today: Friends over Funnels

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

Epic Quotes

• “You have to know yourself before you can go tell others your story.” - Mini Peiris
• “ Nobody buys anything these days without calling up three of their friends. So if a friend's already making the intro, cause they took the leap, you have a better shot.” - Mini Peiris

Connect with Mini

• LinkedIn: https://www.linkedin.com/in/mini8ture/ 
• Website: https://www.nintex.com/ 

Shoutouts

• Matthew Luhn: https://www.linkedin.com/in/matthew-luhn-52a40629/ 
• Geraldine McGinty: https://www.linkedin.com/in/geraldinemcgintymd/ 
• Drift: https://www.salesloft.com/platform/drift 
• HubSpot: https://www.salesloft.com/platform/drift 
• Zendesk: https://www.zendesk.com/ 
• Rippling: https://www.rippling.com/ 
• Lifetime Fitness: https://www.linkedin.com/company/lifetimeinc/ 
• Qualtrics: https://www.qualtrics.com/ 
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 

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What would you say if your CEO told you they wanted to speak with 100 customers in 100 days? That’s exactly what our guest, David Politis, did and he still thinks it’s one of the best things he’s done in his career.

David, the Founder and Executive Chairman of BetterCloud and Host of Not Another CEO Podcast, joins co-hosts Craig Rosenberg and Matt Amundson for a must-listen episode for founders, CEOs, and B2B execs. David explains why having a smaller TAM (Total Addressable Market) is actually good for smaller or newer-stage companies. There are also great discussions about when landing a big customer can be a bad thing for your company’s roadmap, why meeting with customers is so critically important for leaders, and how to stand out as a sales rep to book meetings with decision-makers at ideal customers.

Also, Matt gets a very meaningful head nod and Craig is called an inspiration, a high that his ego may be chasing for a long time.

Critical Takeaways

• Narrow down both your ideal customer profile and your ideal buyer persona. While this may seem counterintuitive, the larger your TAM (Total Addressable Market), the slower your company will grow. When you try to go after too many customer profiles and buyer personas, your budget, time, and effort get dispersed across them and it’s harder to gain a real foothold in any niche from which you can later expand beyond.
• When you focus on one key buyer persona within one ICP (Ideal Customer Profile), you can delve deeper into understanding not only how they will use your product, but also what your product actually means to them. For example, when Matt was working in marketing automation, he was able to understand that his product gave buyers a seat at the revenue table and made their jobs easier.
• Especially for early-stage startups, there is nothing that is more valuable than talking with your customers. Those conversations function as critical data points that you can use in every aspect of the company, from writing messaging and crafting sales narratives to building new features and raising funds. 
• Proving to people that you and your email or message aren’t just automated is harder than ever now, so to really cut through the noise and get noticed, you need to do things that can’t be automated. In-person and handwritten things work well for this.

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 When Craig Met David, His Forever-23-ish Wunderkind

06:07 Stop Supersizing Your TAM, Narrow Down Your ICP

09:34 The Dangers of Landing a Whale Client & How To Handle Your Big Fish

18:11 Which Comes First, The Product or The Persona?

23:19 Why a CEO Would Want to Meet 100 Customers in 100 Days

30:48 Sales Reps Need To Take The Opposite Approach to Automation

41:50 Creating Memorable Moments for Prospects & Customers Through Events

47:50 Matt Provides His Expert Critique of David’s Art Exhibition

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Epic Quotes

• “In the early stage, every customer conversation is gold.” - David Politis
• “There's nothing that you can do that's as valuable as meeting customers, once you're an executive.” - Matt Amundson

Connect with David

• LinkedIn: https://www.linkedin.com/in/davidpolitis/ 
• BetterCloud Website: https://www.bettercloud.com/ 
• Work-Bench Website: https://www.work-bench.com/ 
• Not Another CEO Podcast: https://podcast.notanotherceo.com/ 
• The StartUp Founder Survival Guide: https://www.linkedin.com/posts/davidpolitis_startup-founder-survival-guide-david-politis-activity-7158455968194875393-QVdh 

Shoutouts

• Chris Degnan: https://www.linkedin.com/in/chris-degnan-524470/ 
• Nick Mehta: https://www.linkedin.com/in/nickmehta/ 
• Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ 
• Jon Miller: https://www.linkedin.com/in/jonmiller2/ 
• Ryan Azus: https://www.linkedin.com/in/ryanazus/ 
• Megan Eisenberg: https://www.linkedin.com/in/meageneisenberg/ 
• Warburg Pincus: https://warburgpincus.com/

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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.

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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).

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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

• LinkedIn: https://www.linkedin.com/in/kyleporter/ 
• Website: https://www.salesloft.com/ 
• Kyle’s post about the Marc Benioff Impersonation (with pictures): https://www.linkedin.com/pulse/20141022175506-2446560-how-we-impersonated-the-salesforce-com-ceo-for-one-of-the-best-marketing-hacks-at-dreamforce/ 
• The Puppy Party for #Unleash17: https://x.com/Salesloft/status/872167164123459584 

Shoutouts

• Jon Birdsong: https://www.linkedin.com/in/birdsong/ 
• Mike Damphousse: https://www.linkedin.com/in/damphoux/ 
• Behind the Cloud by Marc Benioff: https://amzn.to/3CE8WXS 
• AJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ 
• AJ Gandhi’s episode of The Transaction: https://thetransactionpod.com/episodes/navigating-market-success-with-aj-gandhi-the-transaction-ep-26 
• Cam Melson: https://www.linkedin.com/in/cameronmelson/ 
• Anthony Zhang: https://www.linkedin.com/in/theanthonyzhang/ 
• Tami McQueen: https://www.linkedin.com/in/tamimcqueen/ 
• Business Insider Article about Benioff for President Campaign: https://www.businessinsider.com/dreamforce-2015-adrian-grenier-wants-to-be-marc-benioffs-running-mate-2015-9 
• Sean Kester: https://www.linkedin.com/in/theseankester/ 
• Mac Reddin: https://www.linkedin.com/in/mac-reddin/ 
• Kevin O’Malley: https://www.linkedin.com/in/omalley/ 
• Peter Kazanjy: https://www.linkedin.com/in/kazanjy/ 
• Carolyn Feibleman: https://www.linkedin.com/in/carolynfeibleman/ 
• Nick Mehta: https://www.linkedin.com/in/nickmehta/ 
• Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ 
• Trish Bertuzzi: https://www.linkedin.com/in/trishbertuzzi/ 
• Steve Richard: https://www.linkedin.com/in/saleskickoffspeaker/ 
• John Barrows: https://www.linkedin.com/in/johnbarrows/ 
• Jason M. Lemkin: https://www.linkedin.com/in/jasonmlemkin/ 
• Mark Suster: https://www.linkedin.com/in/marksuster/ 
• Brad Feld: https://www.linkedin.com/in/bfeld/ 
• Ken Krogue: https://www.linkedin.com/in/kenkrogue/ 

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What does a sales 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 Chief Marketing Officer of Box joins hosts Matt Amundson and Craig Rosenberg to explain how to fix the cracks between sales and marketing in B2B. Tricia outlines the importance of having shared goals across B2B 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 B2B 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 B2B 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 customer or peer 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.

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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 B2B Chief Marketing Officer

04:51 Managing Pipeline in the Current SaaS Environment

08:56 How to Align B2B Marketing and Sales Teams

23:26 Aligning Incentives Across Go-To-Market Teams

24:01 Defining Opportunities and Meetings

25:18 Adapting to AI in B2B Sales

27:13 Transitioning to a New CMO Role in a B2B company

32:22 Building a Customer Community and Product Alignment

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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/ 

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Wow, Season Two is kicking off strong with this incredible episode with Dave Gerhardt, an astonishing marketer and the Founder & CEO of Exit Five. Dave joins Craig Rosenberg and Matt Amundson to share how he approaches using AI for B2B marketing, why LinkedIn influencers present a huge opportunity for B2B brands, and the outsized impact that building a strong Founder Brand can have for startups. 

Also, Matt shares his innermost feelings about Dave and Craig examines his own facial hair.

Critical Takeaways

• Social media should be treated as the primary marketing channel for B2B SaaS brands, not just a supplementary piece of your strategy.
• AI tools are best used as an “idea starter” to get your writing going, rather than relying on the artificial intelligence to do the actual writing itself.
• Working with micro-influencers who have a strong, niche following can be highly effective in B2B SaaS. To see good results, it's important to create offers and content that align with what their audience wants to see. 
• Narrowing down your Ideal Customer Profile (ICP) is crucial for B2B growth. Starting with a more specific market allows for easier traction and learning which you can later apply more broadly as your company scales. 

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New Sponsor coming soon!

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

Chapters

00:00 Matt provides a safe space for Dave

02:06 Discussing Founder Brand and B2B Marketing Strategies

04:45 The Power of Personal Branding and Social Media for Startups

09:42 AI Tools in B2B Marketing: Opportunities and Misconceptions

20:00 B2B Influencers and LinkedIn Strategies for SaaS companies

26:19 Understanding the Full Funnel in B2B Marketing

27:26 The Power of LinkedIn and Social Media

31:18 Narrowing Down Your Ideal Customer Profile (ICP)

37:03 The Story Behind Drift's Success

40:00 Building a Strong B2B Brand and Content Strategy

46:56 An In-depth Review of Craig’s Facial Hair

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Epic Quotes

• “Social media is the way marketing happens in our lives today.” - Dave Gerhardt
• “I use [AI] a lot as my writing partner, you can't really have writer's block anymore because you kind of always have something to get going” - Dave Gerhardt
• “I love you.” - Matt Amundson

Connect with Dave

• LinkedIn: https://www.linkedin.com/in/davegerhardt/ 
• Website: https://www.exitfive.com/ 
• Podcast: https://media.exitfive.com/podcast 

Shoutouts

• Adam Robinson: https://www.linkedin.com/in/retentionadam/ 
• Bland AI: https://www.bland.ai/ 
• HeyGen: https://www.heygen.com/ 
• Danielle Messler: https://www.linkedin.com/in/daniellemessler/ 
• Natalie Taylor: https://www.linkedin.com/in/nataliecstaylor/ 
• Capsule: https://capsule.video/ 
• Planful: https://planful.com/ 
• Mac Reddin: https://www.linkedin.com/in/mac-reddin/ 
• David Politis: https://www.linkedin.com/in/davidpolitis/ 

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