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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/
 
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Too often, sales, marketing and customer success exist in silos—and it’s stifling progress. When all three forces align, businesses thrive and customers get what they actually want and need. When they don’t, it’s easy for business to get “stuck.” On this episode of the Winning The Challenger Sale podcast, we’re joined by Margaret Mueller, Board Dir…
 
With your car, bad tire alignment causes uneven tire wear, diminishing suspension quality, and steering problems that could cause an accident. The same goes for bad sales and marketing alignment—metaphorically, at least. All too often, commercial leaders ignore when two of their most important wheels—sales and marketing—veer off in completely oppos…
 
Sales success is built on understanding others. If you don’t know your buyers, you’re going to struggle to make the sale. If you can’t put yourself in the shoes of your colleagues in marketing, it’s going to be impossible to align. And if you can’t create a culture of inclusivity on your sales team, you miss out on a range of diverse perspectives t…
 
Will there be a recession this year? It seems not even economists can agree, but regardless of how likely it is, the simple fact that it’s possible is brewing uncertainty. So what’s a seller to do? Here to help answer that question is the latest episode of “Winning the Challenger Sale,” where host Andee Harris, CEO of Challenger, is joined by Tim K…
 
The theme for this month on Winning the Challenger Sale is Selling When No One is Buying. WTCS Host Andee Harris, CEO of Challenger, is joined by Shannon Poole, CFO at Challenger, to discuss the roles CFOs play in executive deals, how they protect a business from negative impacts, and the skillsets a CFO needs to make financial decisions. She also …
 
The theme for this month on Winning the Challenger Sale is Selling When No One is Buying. WTCS Host, Andee Harris, CEO of Challenger, is joined by Paul Stansik, Operating Partner at ParkerGale Capital, to discuss the sales executives' role and the pressures they face to increase sales during slow periods of business, and the skills they need to suc…
 
On this episode of the Winning the Challenger Sale podcast, Andee Harris, CEO of Challenger, is joined by Rebecca Grimes, Chief Revenue Officer at Ruby, to discuss skills such as listening skills, storytelling skills and others that are necessary to possess for sales when the market is tough. They also discuss how agility and being a human first ca…
 
On this episode of the Winning the Challenger Sale podcast, Andee Harris, CEO of Challenger, recaps highlights from the second most popular theme from the podcast last year. The goal is to help you kickstart the year on a solid foundation while riding on the wings of these clips. This time, she walks us through deep insights from the theme “Turning…
 
On this episode of the Winning the Challenger Sale podcast, our host Andee Harris, CEO of Challenger, runs through the highlights of our most popular theme from 2022. Tune in to hear non-traditional ideas on effectively deploying storytelling to inspire action and solve your customer’s problem from interviews with Brett Adamson, Nick Capozzi, Ravi …
 
On this special 2022 Year in Review episode of the Winning the Challenger Sale podcast, our new host Andee Harris, CEO of Challenger, runs through the highlights of our most popular episodes from this year. Tune in to hear the best clips from Ravi Rajani, Brandon Fluharty, Jeff Bajorek, Sam McKenna, Will Allred, and Tom Alaimo as they discuss major…
 
The theme for December on Winning the Challenger Sale is a recap of the best insights from 2022. WTCS host, Jen Allen, speaks with Andee Harris, CEO of Challenger, to explore the major themes that have disrupted the status quo of selling this year.โดย Challenger,Inc.
 
The theme for December on Winning the Challenger Sale is a recap of the best insights from 2022. WTCS host, Jen Allen, is joined by Dr. Howard Dover to explore the major themes that have disrupted the status quo of selling this year.โดย Challenger,Inc.
 
The theme for this special episode on Winning the Challenger Sale is Avoiding Death by Discovery. WTCS host, Jen Allen, is joined by Doug Landis to explore the major themes, such as “anti-discovery,” that disrupted the status quo of selling throughout the year 2022.โดย Challenger,Inc.
 
The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host, Jen Allen, is joined by Caroline Franczia to explore how star sellers prepare negotiables and anticipate curve balls ahead of negotiation conversations. In addition, they discuss the similarities and differences between MEDDIC and the Challenger selling …
 
The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host, Jen Allen, is joined by Kyle Asay to discuss how to prepare, anticipate, and mitigate curveballs ahead of negotiation conversations.โดย Challenger,Inc.
 
The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host, Jen Allen, is joined by Niko Papademetriou to discuss techniques used by star salespeople to prepare for negotiations and any surprises that may come up.โดย Challenger,Inc.
 
The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host Jen Allen is joined by Ryan Scalera to discuss how star sellers prepare to open negotiations and anticipate curve balls ahead of negotiation conversations.โดย Challenger,Inc.
 
The theme for October on Winning the Challenger Sale is Creating a Mutual Close Plan. WTCS host Jen Allen is joined by Geoff Hendricks to discuss the importance of ensuring you're on the same page with your buyer about what needs to be done before closing a deal.โดย Challenger,Inc.
 
The theme for October on Winning the Challenger Sale is Creating a Mutual Close Plan. WTCS host, Jen Allen, is joined by Leslie Venetz to discuss the role of a mutual close plan in driving sales success. She sees the close plan as an opportunity to guide a buyer through the buying process towards an outcome beneficial for them and, hopefully, for y…
 
The theme for October on Winning the Challenger Sale is Creating a Mutual Close Plan. WTCS host, Jen Allen, is joined by Anthony Natoli to discuss the importance of mutual close plans; why and how salespeople should use them to enhance their sales processes.โดย Challenger,Inc.
 
The theme for October on Winning the Challenger Sale is Creating a Mutual Close Plan. WTCS host, Jen Allen, is joined by Aaron Evans to discuss how to map out and mutually agree with a customer on the final steps toward closing a deal.โดย Challenger,Inc.
 
The theme for September on Winning the Challenger Sale is Driving Urgency for Change. WTCS host, Jen Allen, is joined by Carl Ferreira to discuss approaches for creating healthy urgency in mid- to late-stage opportunities, especially when progress stalls.โดย Challenger,Inc.
 
The theme for September on Winning the Challenger Sale is Driving Urgency for Change. WTCS host, Jen Allen, is joined by Amelia Taylor to discuss how sales representatives can motivate action in mid to late-stage opportunities, especially when progress stalls.โดย Challenger,Inc.
 
The theme for September on the Winning the Challenger Sale is Driving Urgency for Change. WTCS host, Jen Allen, is joined by Florin Tatulea to discuss how understanding the buyer's position and trying to speak the buyer's language can assist sales professionals uncover the urgency for the buyer to take the necessary action and some strategies for S…
 
The theme for September on Winning the Challenger Sale is Driving Urgency for Change. WTCS host, Jen Allen, is joined by John Shea to discuss how creating urgency allows salespeople to provide customers with real value—by getting the prospects to realize that every day, week, or month without the proposed solution hurts their business, their income…
 
The theme for August on the Winning the Challenger Sale is Resolving Buying Group Conflict. WTCS host, Jen Allen, is joined by Amy Hrehovcik to discuss how to manage the inevitable buying group conflict and dysfunction that arises when you have multiple customer stakeholders getting either directly or indirectly involved in a deal.…
 
The theme for August on the Winning the Challenger Sale is Resolving Buying Group Conflict. WTCS host, Jen Allen, is joined by Charles Muhlbauer to discuss the role that curiosity and discovery play for a seller leading a group meeting in front of a buying group.โดย Challenger,Inc.
 
The theme for August on the Winning the Challenger Sale is Resolving Buying Group Conflict. WTCS host, Jen Allen, is joined by Luigi Prestinenzi to discuss how to manage the inevitable buyer group conflict and dysfunction that arises when you have multiple customer stakeholders involved either directly or indirectly in a deal.…
 
The theme for August on the Winning the Challenger Sale is Resolving Buying Group Conflict. WTCS host, Jen Allen, is joined by Howard Brown to discuss nontraditional ideas for how sellers can manage the inevitable buyer dysfunction that happens when multiple stakeholders are involved in the decision.…
 
In this episode of Winning the Challenger Sale, Jen is joined by Belal Batrawy, Head of GTM & Amateur Meme Maker at GTM Buddy. They discuss how to resolve or mitigate conflict in the modern organizational process of making a purchasing decision, which primarily takes place among a group of executives and managers, as well as how to navigate the per…
 
In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Brandon Fluharty, Founder of Be Focused. Live Great. and Facilitator at Make More Hustle Less Club. They discuss consensus-based selling and how you can take a single interested stakeholder and aid them in their efforts to advocate for you with the broader buying team.…
 
In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Nate Nasralla, Founder of Fluint. They discuss how to sell with your buyers, not to them.โดย Challenger,Inc.
 
In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Jeff Bajorek, Founder, Advisor, and Coach to B2B Sales Leaders at Parabola Consulting and Host of Rethink The Way You Sell. They discuss how you can take a single interested stakeholder and aid them in their efforts to advocate for you with the broader buying.…
 
In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Mor Assouline, Founder of FDTC and Creator of Saas Talks: From Lead to Close Podcast. They discuss sales strategies that convert interested buyers into advocates. How to approach a demo boost consumer delight so that they can proactively recommend your company's produc…
 
In this episode of Winning the Challenger Sale, WTCS host Jen Allen recounts the June theme of persuasive storytelling. She discusses her sales journey and highlights common mistakes salespeople make when telling their stories that leave a buyer in a "no decision" position. She also recommends practical storytelling techniques that are strategic, e…
 
In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Nick Capozzi, Head of Storytelling at Demostack. They discuss how to use descriptive words and ideas to help prospects visualize themselves as part of your story and relate better to the ideas or products you're selling.…
 
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.…
 
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, an…
 
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.…
 
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 tran…
 
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 influenc…
 
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 distingu…
 
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 dilemm…
 
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 …
 
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 insp…
 
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.โดย Challenger,Inc.
 
In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Geoff Hendricks, Key Account Executive at Challenger, and Ari Brinson, Business Development Associate at Challenger, discuss their views and experiences with email marketing and present a framework for producing effective emails that customers love to engage with.…
 
In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Amy Volas, Founder & CEO of Avenue Talent Partners, discusses achieving long-term success in recruiting, marketing and sales. Often, individuals prioritize self-promotion to attract prospects, which is usually rooted in short-term fulfillment goals such as now-now sales. But, w…
 
In this episode of Winning the Challenger Sale, hosts Mike Randazzo and Jen Allen discuss social selling in depth. They discussed how important it is to include the human element in the sales and marketing process and deliver value that engages customers and prospects. They investigate factors that influence great sales, such as how easily customer…
 
In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Josh Braun, Founder of Josh Braun Sales Training, shares his perspective on social selling and how to engage with prospects in a way that flips their defense mechanism to traditional sales processes and allows them to open up to the solution you have to offer.…
 
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