The Transaction

Sam McKenna, Founder of SamSales Consulting and a leading expert in social selling, joins the hosts for a lively discussion. They tackle the importance of personalization in prospecting and share tips on engaging with potential clients authentically on LinkedIn. Sam emphasizes standing out by adding thoughtful comments rather than generic interactions. The conversation also touches on the evolution of go-to-market strategies and the balance between automation and personal touch in sales, with amusing stories sprinkled throughout.

Join Maria Boulden, a seasoned sales expert with over 30 years leading sales teams at DuPont and Gartner, as she shares her energetic insights on modern sales. She humorously debunks the myth that steak dinners close deals, emphasizing the need for authentic connections instead. Maria advocates for senior leaders to engage directly with front-line sellers and adapt to today’s B2B dynamics. With stories of leadership challenges and the importance of personal relationships, she offers invaluable advice for navigating the evolving sales landscape.

Michael King, a leading marketing executive recruiter and author of "Be There When I Return," shares his inspiring journey of battling epilepsy while navigating a successful career. He discusses the importance of chasing the right companies over titles and the need for relevant experience in hiring. Michael also sheds light on how job seekers should consider company culture and growth potential. Additionally, he addresses the evolving tech recruiting landscape and emphasizes storytelling as a powerful tool for raising epilepsy awareness.

Employee churn is a serious problem that is seldom discussed, especially given how much of a detrimental impact it has on even the best companies. To help illuminate this problem and how to fix it at your organization, Katherine Andruha joins co-hosts Craig Rosenberg and Matt Amundson for a much-needed conversation filled with tips, tricks, and a few flamingos.Katherine Andruha is the Vice President of Business Development at Fivetran and has led top-performing sales teams for decades at cutting-edge SaaS companies such as Simpplr, Cloudflare, Coursera, Eightfold.ai, Anaplan, Apttus, and Aruba Networks.Katherine sheds light on where current onboarding programs fall short and shares what can be done so that employees are actually put in the best position to succeed. Additionally, Katherine dives into the importance of properly managing pipeline progression.Also, Craig recounts getting “flocked”, Matt compliments Craig’s athletic abilities, and Sam the Producer grossly mispronounces someone’s name. Critical TakeawaysA comprehensive onboarding process for BDRs is critical. Make sure new BDRs aren’t making live calls until week four. This allows them to become fully comfortable with the systems, processes, and their pitches, minimizing the risk of errors and increasing their initial successes.Utilize AI tools for mock calls to simulate real-world environments. This allows BDRs to practice handling objections and refine their pitches in a risk-free environment before they contact actual leads. Incorporate various channels such as live calls, LinkedIn voice notes, and personalized videos. Ensure that new BDRs are trained to use these channels effectively as people are now more responsive to phone calls and LinkedIn interactions.Ensure that managers have a consistent checklist for onboarding and supporting BDRs. This will help maintain consistency and high standards across teams.Regularly review pipeline stages to ensure there are no stale leads. Utilize automated reminders for deals that have been stagnant for too long to push progression actively.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 Intro06:30 Introducing Katherine Andruha11:23 Onboarding and Training Challenges19:25 Effective Onboarding Practices for B2B SaaS Companies29:05 The Importance of Confidence in BDRs30:37 The Sales Manager's Role in Onboarding33:26 Territory Ownership and AE Handover35:15 Creating a Fun and Productive Environment as a B2B Seller37:45 Pipeline Progression and Accountability42:48 The Role of CMOs in Pipeline Progression44:57 Closed Lost Analysis and Product Feedback48:01 The Importance of Phone Calls48:41 Using Swag to Engage ProspectsSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Know your business. It's the only way you will be taken seriously.” - Katherine Andruha“Just call the leads” - Katherine AndruhaConnect with Katherine AndruhaLinkedIn: https://www.linkedin.com/in/katherineandruha/ Website: https://www.fivetran.com/ ShoutoutsDoug Landis: https://www.linkedin.com/in/douglandis/ Sangram Vajre: https://www.linkedin.com/in/sangramvajre/ Alan Berkson: https://www.linkedin.com/in/alanberkson/ Nooks: https://www.nooks.ai/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

In a world where B2B deals involve more people than ever, growth is suffering. Nick Toman shares insights on how more sellers can actually hinder win rates. The discussion includes three key behaviors that lead to successful sales relationships and how slowing down can paradoxically speed up deals. Sales compensation's role in shaping behaviors is explored, alongside the intriguing concept of 'Headway Selling.' Plus, there are plenty of lighthearted moments, from childhood sports traumas to gnome confessions!

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!

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.

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!

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.

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!