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B2B SaaS and Cloud founders, CEOs, and Go-To-Market operating executives share their journey as they scaled their business from $0M ARR to $100M and beyond. The guests share their insights on measurements of success, performance metrics, and benchmarks they use to guide and inform their decision-making and growth journey.Guests include founders and CEOs of amazing success stories such as LinkedIn, DocuSign, Marketo, Gainsight, Salesforce Commerce Cloud, ringDNA, InsightSquared, Cloudera and ...
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The Transaction

Matt Amundson & Craig Rosenberg

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Welcome to The Transaction. From ABM to PLG, from MEDDIC to MEDDPICC, the world of business is constantly evolving. We’ll cover the who, what, where, when, why and most importantly how you get… The Transaction. Hosted by Craig Rosenberg and Matt Amundson. 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.
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In this episode of The Transaction, Matt Amundsen and Craig Rosenberg are joined by Ray Rike to delve into the world of metrics. Ray shares his passion for allowing SaaS operators to make metric-informed and benchmark-validated decisions by looking at metrics across the entire customer journey. He highlights key metrics such as CAC ratio, inbound h…
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The Transaction’s guest today is one of many talents. Jen Igartua, who is not only the CEO of GoNimbly but also a side hustler in both comedy and board game designing, provides her insights on the sales and marketing world today. The conversation covers transforming B2B sales strategies using signal-based selling and PLG (Product-Led Growth) insigh…
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Today Mark Kosoglow, an experienced sales professional and an advisor at HockeyStack, discusses with Craig and Matt his insightful perspectives on sales strategies. He emphasizes the importance of creativity over sheer volume in outreach and the challenges posed by current sales practices. Mark highlights his approach to sales from his time at Outr…
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This episode brings on Dennis Lyandres as the guest. He is currently an advisor at ICONIQ Capital and has many years of sales, marketing, and strategy experience. Along with Craig and Matt, Dennis discusses effective leadership techniques and the importance of relentless learning in the sales and marketing world. He emphasizes the importance of hir…
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Today’s episode welcomes Sydney Sloan, former CMO of Drata and newest CMO of G2, to sit down with Craig and Matt to give strong insights on the evolving strategies being used in marketing. Sydney discusses the shift from account-based to segment-based strategies, and elaborates on how triangulation of data points can enhance targeting and campaign …
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Today’s episode showcases Craig and Matt as they hear powerful insights from the Founder of Cloud Ratings, Matt Harney, as he discusses the importance of ROI and value selling within the software industry. The conversation begins with a discussion on the underutilization of ROI calculators by software companies, emphasizing how personalized ROI can…
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In today’s episode of The Transaction, hosts Craig and Matt sit down to talk with sales expert Dave Brock. Dave is a well-established sales consultant, the founder and CEO of Partners in EXCELLENCE, and the author of “Sales Manager Survival Guide”. They discuss the pivotal changes required in the sales approach, focusing on customer engagement, win…
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In this engaging episode of The Transaction, hosts Matt Amundsen and Craig Rosenberg welcome Kevin Maney, renowned author of “Play Bigger” and expert in category design. Kevin shares his insights on the importance of creating a unique market category, how to effectively communicate a company’s value, and why businesses need to focus on solving spec…
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In this episode of The Transaction, Matt Amundsen and Craig Rosenberg are joined by Alistair Wolcock, a renowned expert in sales tech and AI. Together, they explore the current trends and future disruptions in sales technology, the importance of user experience, and the concept of signal-based selling. Alistair shares his insights on how enterprise…
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In this episode of The Transaction, Co-Hosts Matt Amundsen and Craig Rosenberg chat with Adam Robinson, founder of a $20 million ARR bootstrapped SaaS company. Adam shares his journey of leveraging LinkedIn for marketing, discussing the power of personal branding and asymmetrical marketing in today’s competitive business environment. He offers insi…
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In this episode of The Transaction, Co-Hosts Matt Amundsen and Craig Rosenberg sit down with Becc Holland, a sales expert known for her innovative approaches to diagnosing and solving sales challenges. They delve into the nuances of effective sales strategies, emphasizing the importance of proper diagnosis over traditional sales tactics. Becc share…
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In this episode of The Transaction, Co-Hosts Matt Amundsen and Craig Rosenberg sit down with John Henry Scherck, a strategic marketing expert with a knack for bold, game-changing moves. Together, they dive into the evolving landscape of content marketing and the importance of taking risks for big wins. John shares his insights on why dipping your t…
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In this insightful episode of The Transaction, Craig Rosenberg and Matt Amundsen are joined by Matt Dixon, renowned author and sales expert, to delve into the complexities of sales indecision. Matt Dixon shares profound insights from his book, The Jolt Effect, and discusses the significant challenges salespeople face today. He breaks down his innov…
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As a GTM leader, you’re probably working every day to improve your playbook and you’re not alone. If improving your sales motions is a serious priority, you should probably check out this episode. Doug Landis is the CEO of DL Advisory and both a renowned sales professional and storyteller. Doug joins Co-Hosts Craig Rosenberg and Matt Amundson for a…
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Please welcome a phenomenal sales thought leader that is bringing some much-needed fresh ideas to the world of B2B sales. Ashley Welch is the Co-Founder of Somersault Innovation and the author of Naked Sales. Ashley joins hosts Craig Rosenberg and Matt Amundson to discuss the core idea of “Selling by Design”, how to craft a collaborative co-creatin…
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Our special guest today is a three-time CMO and seasoned veteran in the customer experience and SalesTech world who offers CX and sales software companies a wealth of expertise that he has accumulated over several decades. Nicolas de Kouchkovsky is a Fractional Chief Marketing Officer & Industry Analyst at CaCube Consulting. Nicolas joins Hosts Cra…
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To help you wrap your head around the rapidly evolving technological landscape as a revenue leader, we have a very special guest today. Mary Shea is the former Principal Analyst at Forrester and is currently advising and coaching multiple high-growth companies. Mary joins Hosts Craig Rosenberg and Matt Amundson to discuss the technology-enabled fut…
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Joining Craig Rosenberg and Matt Amundson in Episode 5 is special guest Chris Orlob, the Co-Founder & CEO of pclub.io. Many of you probably know about Chris or his awesome work early on at Gong which helped the company reach hockey stick level growth. Chris shares his “unqualified” thoughts on when to gate content, how to get deals done on demo cal…
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Joining Hosts Craig Rosenberg and Matt Amundson is John Barrows, the CEO of JB Sales and Author of I Want To Be In Sales When I Grow Up. John outlines what led to the current poor performance amongst sales reps and what leaders can do about it to increase performance today and in the long run. They also get into why buyers dread demos, whether mark…
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Today’s episode is a real treat because we have multiple amazing guests joining Craig Rosenberg and Matt Amundson for a deep dive into the state of MarTech today and how to think about generative AI within the larger AI conversation. Scott Brinker & Esteban Kolsky are two of the foremost thinkers and analysts in the B2B world and are here together …
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Welcome back to The Transaction! In our second episode, you’ll hear from a truly classic Founder who is full of marketing ideas that are disrupting the status quo of B2B marketing. Mac Reddin is the Founder and El Rey de Dinos at Commsor, the company behind both Matcha and Bronto. Mac joins co-hosts Craig Rosenberg and Matt Amundson to save go-to-m…
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Welcome to the first full episode of The Transaction! We’re kicking things off right with an amazing guest who is known for her time as President and COO of Gong, and as Executive Vice President, Sales at Tableau. Kelly Breslin Wright is now the Founder of Culture Driven Sales and an Adjunct professor at the University of Washington. Kelly joins Ho…
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Welcome to The Transaction! This is just a taste of what you can expect from the first four episodes of the show. First Episode drops 3/14 Learn more at https://thetransactionpod.com/ Follow The Show! Social Media: ~LinkedIn: https://www.linkedin.com/company/the-transaction/ ~Substack: https://thetransaction.substack.com/ ==========================…
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Welcome to The Transaction. From ABM to PLG, from MEDDIC to MEDDPICC, the world of business is constantly evolving. We’ll cover the who, what, where, when, why and most importantly how you get… The Transaction. Hosted by Craig Rosenberg and Matt Amundson. Presented by Ringmaster Conversational Marketing, the go-to branded podcast team. To discover …
  continue reading
 
Imagine being a senior product leader at Microsoft for one of the leading "cloud products" in the industry, Azure Data Factory, and deciding to leave the stability, security, and prestige behind to launch your own B2B SaaS company. This is exactly the decision and journey that Anand Subbaraj began five years ago. Anand spent 13 years at Microsoft b…
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Excel is the #1 tool B2B SaaS companies use for many financial tasks, including calculating SaaS metrics to surface insights for operating decisions and investor updates. Ali started his career in tech as an auditor at Ernst and Young, with a priority focus on revenue recognition and reporting. While auditing a top tier B2B SaaS company, he was pro…
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In Episode #1 of this 2-episode conversation, Ray discusses the key findings from the Bessemer Venture Partners (BVP) annual "State of the Cloud" report for 2023 with Janelle Teng, Vice President and co-author of this year's report. Janelle is involved in many different research programs at BVP, including the "State of the Cloud" and the "Scaling t…
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The Alexander Group works with many of the leading companies in the B2B SaaS industry, and I was recently joined by Ted Grossman, their co-lead of the technology industry practice, and Davis Giedt, Director of Research and Analytics. Based upon Ted and Davis' unique insights and understanding of B2B SaaS due to the discussions and data from over on…
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State of the Cloud 2023: Top Five Predictions: #1: Efficient Growth Adopt new solutions to gain control of their Cloud and SaaS spend, including the infrastructure cost to deliver SaaS Solutions. Tools include Cloud FinOps tools, SaaS Spend Solutions, and engineering productivity tools to improve R&D processes. One of the areas of focus is on Cloud…
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Matt Wolach is the founder of Xsellus and host of the Scale your SaaS podcast. Matt is one of those guests that have taken over a year to be on the Metrics that Measure Up podcast. Matt has hosted over 250 episodes of "Scale your SaaS" and was one of the inspirations for this podcast. The first question I asked Matt was about the common attributes …
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In 2023 many SaaS companies are searching for what market(s) are going to drive their next phase of growth - and international markets, especially English-speaking countries are often considered by U.S. B2B SaaS companies. Rick Pizzoli, moved to Europe over 25 years ago to launch the European presence for U.S. based software companies. Based upon t…
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Eric Christopher, the founder, and CEO of Zylo is sitting on top of one of the industry's largest SaaS spend data repositories and thus benchmarks, a key reason I knew I needed to have Eric as a guest on the podcast. What was the catalyst for founding Zylo? It started with Eric's experience as a revenue leader in two social media platform companies…
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SaaS Spend Management is an emerging and rapidly evolving category - yet Ryan Neu, Co-Founder, and CEO of Vendr has a unique vision for how the category needs to evolve. Ryan has a background in public accounting, and then transitioned to software sales, including a role in the early days at Hubspot. During his career selling, he realized that sell…
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If you have ever been frustrated with the forecasting process and accuracy at your company - this episode is for you! Guy Rubin is the founder and CEO of ebsta, a leading provider of Revenue Intelligence - the next generation of forecast management. Guy founded ebsta to automate the logging of sales rep activity directly into their Customer Relatio…
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Friday, March 10th, 2023 - a moment in B2B Technology and Start-Up ecosystem history that many will never forget and hopefully provides a foundation for learning the risks and rewards of venture-backed, early-stage entrepreneurship. Todd Gardner founded SaaS Capital in 2007, the industry's first "recurring revenue credit facility". Before names lik…
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Over February and March 2023, we spoke with several founders, CEOs, and executives at SaaS Spend Management vendors. In this episode of the Metrics that Measure Up podcast, we discussed the evolution, best practices, and ideas on how to introduce a SaaS Spend Management program with Brad Van Leeuwen, Co-Founder and COO at Cledara. Brad stated that …
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Planning in 2020 continues to be chalked full of uncertainty based on the current macroeconomic reality. Assuch, being a finance leader in 2023 is even more challenging, and unpredictable - but developing an operating plan and budget is an important and critical component of the CFO's job. First, is being "hyper-realistic" is the theme of the year,…
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How does writing a 400-page novel lead to founding a SaaS Spend Management company? It was the start of David Campbell's journey which including breaking into B2B technology sales where he saw the challenges companies of all sizes have with buying technology. What is the definition of "SaaS Spend Management" according to David? David defines it as …
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Oded Zehavi has global payment experience from his time as an executive at leaders including PayPal and Payoneer. With Spend Management, especially SaaS Spend Management, becoming such a hot topic in 2023 - we wanted to start our conversation with Oded to understand his definition of "Spend Management"? Oded defines spend management as enabling fin…
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Have you ever met someone in their "early career" that you just knew was going to be successful? That was my feeling when I first met Guy Yalif, Founder and CEO of Intellimize almost 20 years ago! Guy has been both a Marketing and Product leader, which led to his creation of a company focused on optimizing full funnel conversion. Guy's vision is to…
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How many times have you visited a B2B website and cringed at being asked to provide your contact information, including your email just to download a white paper or watch a video? Why is this a reality in 2023 on most B2B SaaS websites? Because "leads" are still a primary measurement of Marketing success and marketers have not yet invested in the p…
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Media-Led Growth (MLG) is a term first introduced here on the Metrics that Measure Up podcast and the central theme of this episode. Who better to discuss this topic than Patrick Campbell, Founder, and CEO of ProfitWell, recently purchased by Paddle for an unofficial $180M+ Patrick was a pioneer in building brand media assets inside a B2B SaaS comp…
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Product-Led Growth is one of the hottest topics and trends in the B2B SaaS industry. Heading into 2023, most company will be evaluating their usage of every SaaS tool, and as a vendor understanding how customers are using your product is foundational to understanding and forecast customer retention metrics. Todd Olso founded Pendo, the leading Prod…
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Mark Roberge is the founder and Managing Director of Stage 2 Capital and previously was the Chief Revenue Officer at HubSpot from 2007 to 2016. Mark is also the author of the best-selling book "The Sales Acceleration Formula". The lessons learned over his nine years leading revenue at HubSpot have led to several new endeavors including creating a S…
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Imagine having your founder and CEO working weekends to develop leads and a calling list for the VP Sales in an early-stage B2B SaaS company. That was Mark Kosoglow's experience when he first joined Manny Medina, the founder, and CEO at Outreach - the leading Sales Engagement Platform company in the industry. I asked Mark about the reality of leadi…
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Heading into 2023 companies are preparing for larger buying teams, and increased scrutiny on every purchase. I could not think of a better backdrop to speak with Brent Adamson, the author of The Challenger Sale and The Challenger Customer. The Challenger Customer is based on research focusing on the different "profiles" of the buying team in a cons…
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Heading into 2023, B2B SaaS CFOs are doubling down on using performance metrics to guide the 2023 operating budget. A key question is what metrics they use to help evaluate the Marketing budget, and what metrics they wish they had from Marketing to help inform budget allocation and investment decisions. Chris Golec, the founder, and CEO of intent d…
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Mergers and Acquisition analyst to FP&A professional to SaaS CFO. This is the path that CJ Gustafson took on his journey to becoming the CFO at Parts Tech. The common thread across each step of his journey was metrics, a perfect subject for CJ's appearance on the show. CJ developed his excel and financial chops during his first role as an M&A analy…
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STOP if you do not think that the concept of "Kind Folks Finish First" is applicable in corporate America! Sam Jacobs, the founder, and CEO of Pavilion realized that getting fired for the third time was the catalyst for finally understanding that pursuing his real passion "to help others" was the key to finding both success and fulfillment. Sam cre…
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