Winning the Challenger Sale
47 episodes - English - Latest episode: almost 2 years ago - ★★★★★ - 25 ratingsWin 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/
Homepage Apple Podcasts Google Podcasts Overcast Castro Pocket Casts RSS feed
Episodes
#44 Creating a Mutual Close Plan with Anthony Natoli, Strategic Account Executive at Lattice
October 11, 2022 12:00 - 33 minutes - 45.6 MBThe 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.
#43 Creating a Mutual Close Plan with Aaron Evans, Co-Founder & Head of Training and Enablement at Flow State
October 04, 2022 12:00 - 36 minutes - 66.4 MBThe 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.
#42 Driving Urgency for Change with Carl Ferreira, Director of Sales at Refine Labs
September 27, 2022 12:00 - 36 minutes - 67.4 MBThe 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.
#41 Driving Urgency for Change with Amelia Taylor, Strategic Sales & Lead Evangelist at regie.ai
September 20, 2022 12:00 - 33 minutes - 76 MBThe 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.
#40 Driving Urgency for Change with Florin Tatulea, Founder at Sales Flo and Head of Sales Development at Plato
September 13, 2022 12:00 - 32 minutes - 59.1 MBThe 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 SDRs and AEs to be successful in sales.
#39 Driving Urgency for Change with John Shea, Global Field Enablement at Databricks
September 06, 2022 12:00 - 38 minutesThe 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, safety, or peace of mind. Hence, they are compelled to take action as quickly as possible.
#38 Resolving Buying Group Conflict with Amy Hrehovcik, Podcast Host & Showrunner at Revenue Real Hotline
August 30, 2022 12:00 - 38 minutesThe 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.
#37 Resolving Buying Group Conflict with Charles Muhlbauer, Lead Enablement Manager at CB Insights
August 23, 2022 12:00 - 37 minutesThe 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.
#36 Resolving Buying Group Conflict with Luigi Prestinenzi, Co-Founder and Head of Growth at Sales IQ Group
August 16, 2022 12:00 - 42 minutesThe 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.
Resolving Buying Group Conflict with Luigi Prestinenzi, Co-Founder and Head of Growth at Sales IQ Group
August 16, 2022 12:00 - 42 minutesThe 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.
#35 Resolving Buying Group Conflict with Howard Brown, Founder and CEO of Revenue.io
August 10, 2022 14:25 - 31 minutesThe 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.
#34 Resolving Buying Group Conflict with Belal Batrawy, Head of GTM & Amateur Meme Maker at GTM Buddy
August 02, 2022 12:00 - 38 minutesIn 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 perplexing behaviors that occur when closing a sale. Belal shares his personal experiences in tactically managing those dysfunctional processes, inclu...
#33 Turning Interest into Advocacy with Brandon Fluharty, Founder of Be Focused. Live Great and Facilitator at Make More Hustle Less Club
July 26, 2022 12:00 - 46 minutesIn 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.
#32 Turning Interest into Advocacy with Nate Nasralla, Founder of Fluint
July 19, 2022 12:00 - 42 minutesIn 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.
#31 Turning Interest into Advocacy with Jeff Bajorek, Founder, Advisor, and Coach to B2B Sales Leaders at Parabola Consulting and Host of Rethink The Way You Sell
July 12, 2022 12:00 - 50 minutesIn 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.
#30 Turning Interest into Advocacy with Mor Assouline, Founder at FDTC and Creator of Saas Talks: From Lead to Close Podcast
July 05, 2022 12:00 - 33 minutesIn 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 products and services to other stakeholders or potential customers.
#29 Persuasive Storytelling with WTCS Host, Jen Allen, Chief Evangelist at Challenger
June 28, 2022 12:00 - 34 minutesIn 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, effective, and beneficial.
#28 Persuasive Storytelling with Nick Capozzi, Head of Storytelling at Demostack
June 21, 2022 12:00 - 36 minutesIn 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.
#27 Persuasive Storytelling with Doug Ferreira, President of Ferreira Sales Training and Consulting
June 14, 2022 12:00 - 44 minutesIn 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.
#26 Persuasive Storytelling with Brent Adamson, Global Head of Research and Communities at Ecosystems
June 07, 2022 12:00 - 47 minutesIn 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.
#25 Persuasive Storytelling with Ravi Rajani, Founder of Ravi Rajani Consulting and Host of The Influential Communicator Podcast
May 31, 2022 12:00 - 42 minutesIn 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.
#24 Opportunity Prioritization with Tom Alaimo, Growth Account Executive at Gong/Millennial Sales & Pavilion Podcast Host
May 24, 2022 12:00 - 31 minutes - 57.7 MBIn 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. Spend...
#23 Opportunity Prioritization with Johnathan Bald, Area Vice President of Large Enterprise Sales Netwitness - Canada & US East at RSA Security
May 17, 2022 12:00 - 35 minutes - 28.2 MBIn 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.
#22 Opportunity Prioritization, with Will Aitken, Sales Evangelist at Sales Feed
May 10, 2022 12:00 - 37 minutesIn 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.
#21 Mike Randazzo’s Farewell Episode
May 03, 2022 12:00 - 29 minutesIn 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.
Mike Randazzo’s Farewell Episode
May 03, 2022 12:00 - 29 minutes - 22.2 MBIn 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.
#20 Email Pitfalls to Avoid, with Sam Mckenna, Founder at #samsales Consulting
April 26, 2022 12:00 - 34 minutesIn 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!
#19 Email Pitfalls to Avoid with Jen Allen and Mike Randazzo
April 19, 2022 12:00 - 48 minutesIn 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.
#18 Email Pitfalls To Avoid, with Will Allred, Co-founder and COO at Lavender
April 12, 2022 12:00 - 34 minutesIn 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.
#17 A Framework for Effective Emails, with Geoff Hendricks, Key Account Executive at Challenger and Ari Brinson, Business Development Associate at Challenger
April 05, 2022 12:00 - 30 minutesIn 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.
#16 Social Selling: Your Secret Weapon in 2022, with Amy Volas, Founder & CEO of Avenue Talent Partners
March 29, 2022 12:00 - 27 minutesIn 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, what if, with a thorough understanding of a niche's issue, one could engage an audience in a substantive discussion, leading to meaningful interacti...
#15 Social Selling: Your Secret Weapon in 2022 with Jen Allen and Mike Randazzo
March 22, 2022 12:00 - 38 minutesIn 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 customers connect with stories, especially ones that highlight challenges they are facing and how you have enabled better outcomes for other customers lik...
#14 Social Selling: Your Secret Weapon in 2022 with Josh Braun, Founder of Josh Braun Sales Training
March 15, 2022 12:00 - 31 minutesIn 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.
#13 Engaging C-Level Buyers with Richard Perez, Lead Advisor for Sales and Go-to-Market Practice at Apax
March 08, 2022 13:00 - 25 minutesIn this episode of Winning the Challenger Sale, hosted by Jen and Mike, Richard Perez, Lead Advisor for Sales and Go-to-Market Practice at Apax, presented ideas on how to approach C-level buyers, how to deal with problems by offering unique insights into their viewpoints, and how to turn those insights into practical solutions. He shares his views on how to engage with C-level buyers on a human level, as well as the significance of prior preparation for a meaningful conversation with them.
#12 Engaging C-Level Buyers with Jen Allen & Mike Randazzo
March 01, 2022 13:00 - 26 minutesIn this episode of Winning the Challenger Sale, hosts Mike Randazzo and Jen Allen dive deep into this week's theme of "engaging C-level buyers". They investigate factors that will make selling difficult in 2022, focusing on the complexity of the expanding buyer's side as a result of increased risk aversion to the traditional solo buyer role. Listen to Mike and Jen explain the shift from the traditional perspective of autonomous purchase consideration by the C-level suite to the need of the se...
#12 Engaging C-Level Buyers with Jenn Allen & Mike Randazzo
March 01, 2022 13:00 - 26 minutes - 36.8 MBIn this episode of Winning the Challenger Sale, hosts Mike Randazzo and Jen Allen dive deep into this week's theme of "engaging C-level buyers". They investigate factors that will make selling difficult in 2022, focusing on the complexity of the expanding buyer's side as a result of increased risk aversion to the traditional solo buyer role. Listen to Mike and Jen explain the shift from the traditional perspective of autonomous purchase consideration by the C-level suite to the need of the se...
#11 Engaging C-Level Buyers with Ian Koniak, Founder & President of Ian Koniak Sales Coaching
February 22, 2022 13:00 - 32 minutesIn this episode of Winning the Challenger Sale, hosted by Jen and Mike, Ian Koniak, Founder & President at Ian Koniak Sales Coaching, shares how to engage C-level buyers, convince them to take the meeting, and then ensure those meetings are productive. He shares his formula for cold emailing, what to say during those meetings, and then how to connect with C-level buyers on both a human and professional level.
#10 The Negotiation Curveball
December 16, 2021 08:00 - 36 minutesIn this episode, hosts Mike Randazzo and Jen Allen talk all about late-stage negotiations. You're wrapping up late-stage deals that you've been working on for months, you're in the final mile, and then... procurement throws you a curveball. An unexpected request, demand, or ultimatum that you weren't anticipating and you're rushing to come up with a response at the moment. But, what if the perfect response is actually no response at all? Or a delayed response? Listen to hear Mike and Jen un...
#9 The Objection
November 18, 2021 08:00 - 29 minutesDoes this sound familiar? You're too expensive. The timing isn't right. We're happy with the solution we have. If there's one topic that's truly universal in B2B selling, both in terms of how often sellers face it and one of things sellers hate the most, it's objection handling. But what if we told you that most sellers approach objection handling all wrong? On this episode, Mike and Jen share a completely different way to approach customer or prospect objections.
#8 The Group Meeting
October 21, 2021 08:00 - 38 minutesInsight-selling in a one-to-one customer conversation is one thing. But how do we do it effectively in front of the entire buying group? Check out this month's podcast to learn more.
#7 The Business Case for Change
September 16, 2021 09:00 - 37 minutesOn this month's episode, hosts Mike Randazzo and Jenn Allen talk all about building a case for change. Change initiatives or purchases are hard for customers to commit to, especially in uncertain times. But what does it take to get a risk averse buyer to move off of their status quo in this environment? The answer: a rock solid business case for change built not only on rational, quantitative evidence, but also on an appeal to the emotional drivers of purchase decision making.
#6 The Value Demo
August 19, 2021 10:00 - 37 minutesOn this month's episode, hosts Mike Randazzo and Jen Allen talk demos. The good, the bad and the ugly. Every sales person needs to demo their product or solution in some way, at some point, but the reality is there is much more that can go wrong with demos than right. Listen as Mike and Jen discuss demo traps to avoid, and the characteristics of best in class demos to keep in mind as you lead them at any stage of the sales process.
#5 The Territory Plan
July 22, 2021 08:00 - 32 minutesHow should I prioritize my pursuits and protect my limited time?Listen to hear hosts Mike Randazzo and Jen Allen discuss how Challengers prioritize their pursuits, whether halfway through the year or beginning with a completely new territory.
#4 The Teaching Opportunity
June 25, 2021 07:00 - 39 minutesHave I earned the right to ‘teach’ my customer yet?Listen to hear hosts Mike Randazzo and Jen Allen discuss how Challengers leverage credibility building and effective questioning to then introduce the right insight, at the right time.
#3 The Discovery Call
May 20, 2021 09:00 - 47 minutesOn this episode of the Winning the Challenger Sale podcast, hosts John Shea and Mike Randazzo and guest, Jennifer Allen, break down how to get the discovery call right. Discovery is a critical component of most sales processes, yet it's often misunderstood or overlooked in its importance. Listen to learn strategies and tactics sales professionals can use to unlock information and deliver value in early stage discovery calls with prospects and customers.
#2 The Introduction
April 22, 2021 09:00 - 39 minutesOn this episode of the Winning the Challenger Sale podcast, hosts John Shea and Mike Randazzo discuss the importance of showing up with credibility in your first interaction with a new client or prospect. Our first guest Jen Allen, Key Account Executive at Challenger, will share her experience with demonstrating credibility and making a strong first impression on the first sales interaction with a prospect, and the prep work you can do to make sure you're prepared.Our second guest, Kristina ...
#1 The Negotiation
March 18, 2021 08:00 - 23 minutesOn the first episode of the Winning the Challenger Sale podcast, hosts John Shea and Mike Randazzo talk all about negotiations - one of the aspects of the sales process that sellers are least confident in. Joined by guest Lauren Graves, Challenger's Head of Learning and Design, they discuss 'sizing the pie' versus 'protecting the pie', how Challengers deal with curveballs, and how to handle the anxiety called "torschlusspanik" in advance of the negotiation.