The Transaction

Carilu Dietrich & Maya Spivak joined Craig, Matt, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording where they shared insights on building founder and executive organic social media as a primary demand channel, why startups need to develop speed as a marketing skill, and why going viral on social doesn’t amount to what it seem for B2B companies...

Dan Kimball is a GTM Advisor, AI Architect, and independent consultant at The Operating Partnership LLC. Dan’s a marketing expert with a bevy of amazing experiences to draw on, from serving as CMO of Spectrum Equity and ThisMoment, to VP of Marketing at Yelp, and SVP of Global Marketing at Eventbrite. Dan joins co-hosts Craig Rosenberg and Matt Amundson to dive into what sets great B2B brands apar...

Back for her second episode is the one and only Jen Igartua, the CEO of Go Nimbly and RevOps OG. Jen joins Co-Hosts Craig Rosenberg and Matt Amundson to break down what made Go Nimbly’s Rev Fest such an incredible event for everyone, from the GTM leaders attending to the speakers, and even the sponsor brands. Jen outlines why she picked a truly iconic venue for a business event, how she prepared t...

Sydney Sloan, the CMO of G2, joined Craig, Matt, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording where she outlined the major shift in B2B buyer behavior, how to measure and track Answer Engine Optimization, and why the partnership and distribution layer is as important as content creation. Critical Takeaways Over half of B2B buyers (51%, up from...

The one and only Scott Albro once again returns to The Transaction, but this time, Scott joined Craig, Matt, James Kaikis, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording. Scott shares his insights on how to overcome the real GTM problem of the ‘attention bottleneck’ and lays out a precise framework for flipping from push to pull using network th...

It’s not every day that you get to have one of the most important thinkers in the startup world on your podcast, but for The Transaction, that day is today. Eric Ries is a Founder and the renowned business author of The Lean Startup and his brand new book, Incorruptible: Why Good Companies Go Bad…and How Great Companies Stay Great. Eric joins Craig Rosenberg and returning guest host Scott Albro to...

Excessive admin work and poor-performing sales plays are killing SDR effectiveness and, in turn, company growth. We just so happen to know just the B2B sales expert to help SDR leaders kick things up a notch, wherever they may reside around the globe. Besides having a wonderful British accent, which Craig loved, David Wilkins is the Founder of SDR Leaders of EMEA and the Co-Founder of SDR Leaders...

Kacie Jenkins is the Head of Marketing for Claude Code at Anthropic. Prior to joining Anthropic, Kacie led marketing at Sendoso as SVP of Marketing, Sourcegraph as VP of Marketing, and Fastly as VP of Marketing, to name a few. Kacie joins co-hosts Craig Rosenberg and Matt Amundson to unpack what B2B brands need to learn from B2C companies in order to build bold, unforgettable brands that increase...

Udi Ledergor is the Chief Evangelist at Gong and is firmly amongst the upper echelon of the, as yet to be founded, B2B marketing leader hall of fame, having led outstanding teams as both a Vice President of Marketing and Chief Marketing Officer at five B2B SaaS companies for over two decades. Alongside steadfast co-hosts Craig Rosenberg and Matt Amundson, Udi shares how he has crafted one of the t...

We’ve got the perfect guest to help you understand how your brand can stand out and provide a uniquely incredible experience for customers in the AI era. Stacey Epstein is the CEO of Structured, the only AI-native channel marketing platform purpose-built for complex partner ecosystems. She is also the Host of AI’ve Got Questions , a casual, candid podcast for marketers trying to make sense of the...

The landscape of go-to-market in the B2B SaaS world is shifting rapidly, but thankfully we’ve got just the person to help you get ahead and innovate. James Kaikis is the Founder of GTMshift, Co-Founder of SolutionExec, Co-Founder of AI Sales Studio, and Host of The GTMshift Interview Series. James joins Matt Amundson and Craig Rosenberg to unpack the evolving role of sales reps, how to use the GTM...

Surprise: Doing ‘more with less’, doesn’t actually work in B2B marketing, and today’s guest has the data to show it. Omar Akhtar is the Founder and Principal Analyst of Benchmarker and the Director of Content at UserTesting. Omar joins co-hosts Matt Amundson & Craig Rosenberg to dive into the B2B marketing data from Benchmarker’s latest survey, why the most successful companies are spending mo...

For our first episode of the new year, we’re thrilled to welcome special guest Kathy Macchi,  the Executive Vice President, Innovation & Co-Founder at Inverta. Kathy joins co-hosts Craig Rosenberg & Matt Amundson to discuss where so many go-to-market leaders go wrong with their segmentation, why your message matters more than the channel you deliver it through, and how to design a successf...

If you feel like your pipeline is broken, your CAC is bloated, and your dashboards are lying to you… you’re FAR from the only one.  Joining the show are the Metrics Brothers, Ray Rike and Dave Kellogg! Ray is the Founder & Chief Evangelism Officer of Benchmarkit, Host of Metrics That Measure Up, a Founding Member of the SaaS Metrics Standards Board, and is an LP at Stage 2 Capital. Dave co-hos...

With so much attention within the go-to-market world paid to marketing and sales, account management, which is arguably just as important, rarely gets its due. Alex Raymond is the Founder of AMplify and Host of the Account Management Secrets podcast. Alex joins co-hosts Matt Amundson and Craig Rosenberg for the first major discussion on the podcast of account management and its crucial role in gro...

The immense hype around AI agents is positively palpable, but is there value in adopting an army of AI minions today or is the promise of agentic AI still fictitious pulp? Here to help illuminate and elucidate the role of AI agents is Gabe Larsen, the Chief Revenue Officer at Signals and the former Chief Marketing Officer of Kustomer.  Gabe joins co-hosts Matt Amundson and Craig Rosenberg for a de...

The vast majority of companies that think they are running ABM (Account-Based Marketing) are not actually running ABM. Not only that, they wouldn’t recognize a real ABM strategy if one came up and slapped them in the face with a stack of direct mailers. Davis Potter is the CEO & Co-Founder of ForgeX, a research and advisory firm that helps B2B companies modernize their Account-Based Go To Mark...

Rachel Dines is a B2B Marketing expert and advisor to multiple SaaS platforms, where she provides her specialty in deep tech companies with sales-led go-to-market motions. Rachel also writes a SubStack newsletter called Tech Dropout. Previously, Rachel was VP of Product and Technical Marketing at Chronosphere and a Forrester industry analyst turned product marketing leader. Rachel joins co-hosts C...

Even with all the newest, shiniest AI tools out there, successful, sustainable B2B sales growth is still built on nailing the basic sales skills. To provide a refresher on those basic B2B sales skills and more, we’re thrilled to introduce Tom Murtaugh, the Portfolio Operations Director at Nordic Capital, a leading sector-specialist private equity firm. Tom joins co-hosts Craig Rosenberg and Matt A...

B2B sellers and sales leaders find themselves in the midst of an unprecedented Go-To-Market skills crisis at a time when budgets are shrinking and selling is getting harder. Joining the show once again is the inimitable Chris Orlob, CEO at pclub.io, the #1 Skill Transformation Platform for Revenue Teams. Chris joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into where the current sales ski...

The old go-to-market playbook is broken, but in this episode we have a B2B SaaS founder who has actually figured out the new GTM playbook to grow in the current market. This SaaS savant is none other than the one and only David Boskovic, the CEO and Founder of Flatfile, which is the AI-powered data migration solution trusted by enterprise customers like ClickUp, HubSpot, Amazon, ADP, and Toast. Da...

80% of B2B buyers are already using AI in some part of their research process. Yes, you read that correctly, and we’ve got a special, repeat guest on the show to help you understand that shift in buyer behavior, how to capitalize on it, and much more. We are thrilled to welcome back AI and marketing expert Sydney Sloan, the Chief Market Officer of G2, to the program on this episode. Sydney joins C...

Imagine you created a sales process so amazing that it was the only one customers actually enjoyed. Impossible? Today’s guest says no. Returning once again to grace this humble GTM-focused podcast with his immense intellect and immaculate presence is Brent Adamson, the co-author of The Challenger Sale and the upcoming new release, The Frame-Making Sale . Brent is back alongside Co-Hosts Matt Amund...

What if cold calling isn’t dead—but everything we know about it is? From dissecting permission-based openers to dunking on dated tactics, sales experts Justin Michael and Charles Needham make a bold case for why the phone isn’t dead as a sales channel—it’s just misused.  Justin Michael, aka the John Wick of executive coaching, is a longtime B2B seller and sales trainer, as well as the Founder of t...

In the second episode of 'The Direct Deposit,' Matt Amundson and Craig Rosenberg dive into the astonishing growth of Cursor, a startup providing an AI code editor for software developers, that has secured three funding rounds and achieved $500 million ARR in less than a year—all without a traditional marketing strategy. Matt & Craig explore how Cursor's product-led growth go-to-market model an...