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The Transaction

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Feb 20, 2025 • 56min

Identifying & Developing a Champion Buyer with Krysten Conner - Ep. 43

There’s a lot of confusion about how to find the champion of your product within a buying group.To help sort things out for B2B sellers, we invited Krysten Conner on the show! Krysten is an extraordinary sales coach who is hired by top SaaS revenue organizations to train their sales teams into incredible teams. Krysten has also made a number of courses available for purchase through her website and through pclub.io. Krysten joins co-hosts Matt Amundson and Craig Rosenberg to break down three ways to identify and develop strong champions within the buying group to help you close more deals. Krysten also shares the secrets to mastering multi-threading for sellers and how to maintain deal momentum with prospects so they become customers.Also, Craig shares the playbook he used to land his first girlfriend, Matt adds an “s” where he shouldn’t have, and Sam the Producer puts his foot squarely into his big mouth.Critical TakeawaysThere are three ways to proactively discover a champion within a prospect's buying group: 1. Do they do work asynchronous of your meeting with them? 2. Do they bring other people to follow-up meetings? 3. Do they have a point of view on the next steps?The first person to reach out or take a meeting with a seller is not necessarily the champion within that organization for your product or service. Don’t make the mistake of assuming they are the champion. Talking with you makes them a contact, not a champion, by default.“Typically” is a magic word to use in your sales calls. Buyers are very risk-averse and want to be sure they’re not doing something wrong that will get them fired. By sharing what other buyers “typically” do when it comes to things like next steps, you can give buyers peace of mind. Buyers aren’t experts at buying your product, so you need to teach them and guide them to make the right decision. This process of educating buyers and helping them avoid common pitfalls makes them feel much more comfortable.Sponsored SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Intro03:44 - The "Let Me Help You Get this Car" Story07:24 - Krysten’s Embarrassing Sales Stories13:22 - Develop a Champion, Don’t Wait For Them to Show Themselves18:39 - Examples of Asynchronous Work that Champions will Do25:58 - Champions will Bring More People to Follow Up Sales Calls32:36 - Craig Details how he Landed his First Girlfriend33:35 - Who Should be Doing Asynchronous Work Within The Buying Committee41:54 - Does Your Buyer have a Point of View on the Next Steps44:54 - Mass Email Does Not Count as Multi-Threading51:10 - Who a Champion Is and What They Will Do in The Buying CycleSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ You multi-thread, by single threading.” - Krysten Conner“ When I'm sending actually any email, if it's no one's baby, it's an orphan.” - Krysten ConnerConnect with Krysten ConnerLinkedIn: https://www.linkedin.com/in/krystenconner/ Website: https://krystenconner.com/ Access the Free Slides Krysten Shared in this Episode: https://docs.google.com/presentation/d/1DOf9bsPh0m7WtQxwhlJfT7Yg22LkD3iukivIk0W1cOA/edit?usp=sharing ShoutoutsChris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris Orlob's Episode of The Transaction:Krysten’s Multi-Threading Course with pclub: https://go.pclub.io/multi-threading-masterclass Mark Kosoglow: https://www.linkedin.com/in/mkosoglow/Mark Kosoglow's Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=falseScott Barker: https://www.linkedin.com/in/ssbarker/Scott Barker's Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/selling-like-a-real-human-being-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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Feb 14, 2025 • 50min

Positioning is a Key Pillar of SaaS Growth with Bob Wright - Ep. 42

Bob Wright, Founder of Firebrick Consulting, brings decades of expertise in B2B tech positioning to the discussion. He emphasizes the importance of 'selling the problem, not the product' to create urgency for buyers. Bob outlines three pivotal questions your positioning must answer: Why now? How are you different? Why does it matter? The conversation also covers the complexities of positioning post-acquisition and the evolving buyer landscape in SaaS, alongside insights on validating strategies with limited resources.
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Feb 6, 2025 • 56min

Selling like a Real Human Being with Scott Barker - Ep. 41

Selling B2B has always been hard. The crazy buying frenzy of the ZIRP era was the exception, not the rule, so if you’re expecting the current buying climate to change any time soon, you need to readjust your perspective.Scott Barker, Partner & Co-founder of GTMfund and Host of The GTM Podcast, joins Host Craig Rosenberg and special guest-host Scott Albro to talk all things sales, venture capital, and go-to-market. Scott (Barker) shares why focus can give sales reps superpowers, the outsized impact of warm introductions when building pipeline, and how focusing on uniquely human skills can help you excel in sales. There’s also some great discussion around the importance of accountability and ownership throughout your go-to-market team.Also, Craig pitches both Scotts on launching a legal practice, Scott Albro relives the glory days of selling TOPO services, and Sam the Producer attempts to crack the case and catch the Bottle Cap Culprit.Critical TakeawaysInvest time in becoming an expert in the problems you are solving for your customers. Offer valuable insights that make clients see you as invaluable.Focus on the human side of sales, including trust-building and relationship management; that’s what closes deals. Rely less on pure automation or technology and more on human connections.Sellers can emulate what works in founder-led sales by using personal testimonies about why they joined the company or how the product solved a problem for them. This can make their pitch more relatable and compelling.Warm introductions are the best way to build pipeline in what is quickly becoming an AI-dominated selling landscapeSponsored SegmentThe Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 Intro00:26 Retreading Brent Adamson’s Maggots on a Plane Story02:30 Introducing Scott Barker05:10 Funny Fundraising Stories08:33 The Importance of Humanizing Sales12:59 Overcomplicating Pipeline Generation16:25 The Human Side of Sales19:39 How to Build Trust in Sales22:08 Expertise in Sales: Lessons from TOPO29:46 The Concept of “Opinionated Software”34:39 Overcomplicating Pipeline Generation38:19 The Power of Warm Introductions43:36 Scaling Founder-Led Sales52:59 The Value of Human Skills in the Age of AISign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ If you even have the thought of an excuse as a sales leader, as a seller, as a marketer, you're already dead in my books.  It requires full and complete accountability.” - Scott Barker“ If there are things that are stopping you from doing your job, it is nobody else's problem, but your own” - Scott BarkerConnect with Scott BarkerLinkedIn: https://www.linkedin.com/in/ssbarker/ GTMfund Website: https://www.gtmfund.com/ GTMfund’s new fundraising announcement: https://techcrunch.com/2025/02/04/how-max-altschuler-accidentally-founded-a-vc-firm-that-just-raised-another-54m/ GTMnow Website: https://gtmnow.com/ The GTM Podcast: https://gtmnow.com/tag/podcast/ ShoutoutsBrent Adamson: https://www.linkedin.com/in/brentadamson/ Brent Adamson’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Max Altschuler: https://www.linkedin.com/in/maxaltschuler/  Javier Soltero: https://www.linkedin.com/in/jsoltero/ ZendeskAnthropicMicrosoftGoogleNeil Harrington: https://www.linkedin.com/in/neildharrington/ Jim Cyb: https://www.linkedin.com/in/jimcyb/ Vinny Pazienza, AKA Vinny Paz and Vinny “The Pazmanian Devil" PazienzaBleed For This (2016, Ben Younger)Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
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Jan 30, 2025 • 1h

Reframing B2B Sales to Drive Buyer Confidence with Brent Adamson - Ep. 40

Brent Adamson, co-author of The Challenger Sale and a renowned sales advisor, joins to share insights on boosting buyer confidence in B2B sales. He discusses how lack of decision-making confidence can lead to stalled deals. Brent emphasizes the need for sellers to teach buyers throughout the purchasing process and the importance of involving implementation teams early. He also explores misconceptions in sales strategies and how to redefine the sales role to facilitate collaboration, ultimately enhancing customer trust and success.
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7 snips
Jan 23, 2025 • 53min

Leading in Your Own Voice with Dia Bondi - Ep. 39

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.Join our Newsletter: https://thetransaction.substack.com/Critical TakeawaysWhen 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.Sponsored SegmentThe Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Intro00:20 - Craig comes Straight Outta Compton00:58 - Fun Facts about Dia Bondi, Matt, & Softball04:09 - Introducing Dia Bondi08:20 - The Impact of Establishing Your Voice12:13 - What is Founder Unrest & When Does It Show Up?15:19 - How Founders can Find Their Own Voice & Unlock Their Origin Story20:42 - Why Understanding How to Tell Your Origin Story Matters31:12 - Dump the Live Demos from your Presentations33:15 - Wait, How Expensive are All-Hands Meetings?38:20 - Two Big Misconceptions about Communication43:44 -  Examples of Leaders with Great Perspectives & Well-Developed Voices50:04 - Craig Compliments Sam for Displaying Basic Competence50:24 - Wrapping UpEpic 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 BondiConnect with DiaLinkedIn: 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: BallparkShoutoutsClaire 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!
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7 snips
Jan 16, 2025 • 1h 6min

Unlocking the Cheat Code for Go To Market with Justin Gray - Ep. 38

Justin Gray, Co-founder of In Revenue Capital and author of "The Go-to-Market Cheat Code," shares his expertise on building successful B2B partnerships. He emphasizes the importance of executive alignment and transforming relationships one person at a time. Discussing the evolving landscape of marketing, Justin warns against copying others and advocates for innovative strategies. He also delves into what investors look for in founders today, highlighting the necessity of value-driven, trust-based marketing.
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18 snips
Jan 9, 2025 • 1h 3min

Helping Every Startup Founder Tell Their Story with Scott Albro - The Transaction - Ep. 37

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 TakeawaysFor 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 SegmentRingmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Walking Through a Winter Wonderland03:23 - Introducing Scott Albro10:51 - AI Adoption is Taking Us Down the Wrong Path13:20 - The Important AI Debates Happening Today16:03 - Where AI Agents & Co-Pilots Fit into Go-To-Market27:20 - Using AI on LinkedIn37:47 - Creating Quality Content47:29 - Scott's Framework for Which Story Founders Want To Tell50:22 - Examples of The Best Founder Brands57:21 - The Impact of Scott's Shoe Game on the MarketEpic 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 AlbroConnect with Scott AlbroLinkedIn: https://www.linkedin.com/in/scottalbro/  ShoutoutsChris 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=3iae7zMatt 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=3iae7zDavid 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=3iae7zJohn 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=3iae7zGartner: 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!
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Dec 19, 2024 • 1h 1min

THE Blueprint for B2B Go-To-Market with Adam B. Needles - The Transaction - Ep. 36

Adam B. Needles, CEO of Annuitas and author of "The Chief Growth Officer's Handbook," shares his sharp insights on B2B go-to-market strategies. He argues that the current challenges in the B2B buying experience often stem from the CMO's role. Adam outlines the three essential components for an effective GTM blueprint: understanding the buyer's journey, identifying stakeholders, and knowing their content habits. He warns that no amount of AI can mask a flawed strategy, pushing for a more cohesive and buyer-centric approach in marketing.
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37 snips
Dec 12, 2024 • 57min

Your Buyers Are People Too with Mini Peiris - The Transaction - Ep. 35

Mini Peiris, CMO of Nintex, dives into the human side of B2B marketing, stressing the importance of connecting with the people behind the transactions. She discusses building brand affinity by understanding buyer needs and goals. The conversation shifts to the crucial role of the CMO in post-sale customer engagement, highlighting strategies for ongoing customer success and advocacy. Additionally, Mini shares insights on effective collaboration with sales and the need for a unified internal brand culture, ensuring every interaction feels meaningful.
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13 snips
Dec 5, 2024 • 50min

Narrow Down Your Damn ICP with David Politis - The Transaction - Ep. 34

David Politis, Founder and Executive Chairman of BetterCloud and host of Not Another CEO Podcast, shares his insights on B2B marketing and SaaS growth strategies. He recalls his transformative experience of speaking with 100 customers in 100 days. David argues that a smaller Total Addressable Market (TAM) can drive faster growth for startups and stresses the importance of narrowing down the Ideal Customer Profile. He emphasizes building authentic customer relationships and tailoring strategies to specific segments for better engagement.

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