
Winning the Challenger Sale
Win the sales moments that matter, every day. Take a deep dive into the day-to-day skills and behaviors proven to win in complex selling and buying environments. Hosted by the team that brought you the best-selling books, "The Challenger Sale" and "The Challenger Customer."Learn more about our "Winning the Challenger Sale" webinar series here: https://www.challengerinc.com/events/
Latest episodes

Jun 14, 2022 • 45min
#27 Persuasive Storytelling with Doug Ferreira, President of Ferreira Sales Training and Consulting
In this episode of Winning the Challenger Sale, Jen is joined by Doug Ferreira, President of Ferreira Sales Training and Consulting. They discuss storytelling as an investment in creating a collaborative atmosphere for a customer with the goal of generating active engagement and a positive sales outcome.

Jun 7, 2022 • 48min
#26 Persuasive Storytelling with Brent Adamson, Global Head of Research and Communities at Ecosystems
In this episode of Winning the Challenger Sale, Jen is joined by Brent Adamson, the Global Head of Research and Communities at Ecosystems and former Distinguished Vice President at Gartner. They discuss persuasive storytelling from the perspective of using emotional selling to start a conversation, pique interest, influence purchasing decisions, and build long-term relationships by focusing on a customer's feelings rather than logic or the product's features.

May 31, 2022 • 43min
#25 Persuasive Storytelling with Ravi Rajani, Founder of Ravi Rajani Consulting and Host of The Influential Communicator Podcast
In this episode of Winning the Challenger Sale, Jen is joined by Ravi Rajani, Founder of Ravi Rajani Consulting and Host of The Influential Communicator Podcast. They explore some persuasive ideas for how sellers can use storytelling to motivate action and convey the human impact of the customer problem we're solving.

May 24, 2022 • 32min
#24 Opportunity Prioritization with Tom Alaimo, Growth Account Executive at Gong/Millennial Sales & Pavilion Podcast Host
In this episode of Winning the Challenger Sale, Jen is joined by Tom Alaimo, Growth Account Executive at Gong/Millennial Sales and Pavilion Podcast Host. They discuss approaches for optimal opportunity identification, assessment, and prioritization. Tom shares personal experiences and vivid illustrations of why he believes it’s important to be transparent about value propositions. He suggests establishing a clients' stance early in a sales conversation before validating any possibility. Spending time verifying the possibility is preferable to leaving things to chance and assuming the sale goes through.

May 17, 2022 • 36min
#23 Opportunity Prioritization with Johnathan Bald, Area Vice President of Large Enterprise Sales Netwitness - Canada & US East at RSA Secur
In this episode of Winning the Challenger Sale, hosted by Jen, Johnathan Bald, Area Vice President of Large Enterprise Sales Netwitness - Canada & US East at RSA Security, discusses the fundamentals of qualifying, disqualifying, and prioritizing opportunities. Johnathan explains how the unique market fit and the maturity of an organization influence the likelihood of qualifying or disqualifying a prospect, and factors that influence internal opportunity prioritization.

May 10, 2022 • 39min
#22 Opportunity Prioritization, with Will Aitken, Sales Evangelist at Sales Feed
In this episode of Winning the Challenger Sale, hosted by Jen, Will Aitken, Sales Evangelist at Sales Feed, discusses opportunity prioritization in prospecting. They discuss the need to prioritize prospects to focus major efforts on the discussions and clients that are most likely to result in a successful sale. Aitken elaborates on how to distinguish your top prospects from a list of several hundred potential clients.

May 3, 2022 • 30min
#21 Mike Randazzo’s Farewell Episode
In this episode of Winning the Challenger Sale, Jen Allen hosts Mike Randazzo's farewell session, which is his final episode as a co-host. They talk about the key concepts behind the Challenger sales strategy, as well as the most memorable experiences and discoveries they've had over the years. Mike discusses his experiences, techniques, and dilemmas while working with Challenger. He also highlights the fundamental concepts and timeless strategic differentiators in sales approaches.

Apr 26, 2022 • 36min
#20 Email Pitfalls to Avoid, with Sam McKenna, Founder at #samsales Consulting
In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Sam McKenna, Founder at #samsales Consulting, discusses differentiation strategies for sales emails. They delve into finding the proper balance between personalization and relevance in email outreach. Sam explains in detail her ‘Show Me You Know Me’ approach. You don’t want to miss this!

Apr 19, 2022 • 50min
#19 Email Pitfalls to Avoid with Jen Allen and Mike Randazzo
In this episode of Winning the Challenger Sale, hosts Mike Randazzo and Jen Allen discuss engaging prospects via email marketing using both the strategic and human approaches. They investigate ways to improve the email recipient’s experience by arousing their curiosity with findings obtained from your interest in the relevant issue, eventually inspiring a natural response.

Apr 12, 2022 • 35min
#18 Email Pitfalls To Avoid, with Will Allred, Co-founder and COO at Lavender
In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Will Allred, Co-Founder and COO of Lavender, presents ideas on writing emails that people want to respond to. They discuss interesting factors that influence customer reaction to email outreach.
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