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 talks about cost of inaction (COI) vs return on investment (ROI), which is more critical to business growth. Shannon offers guidance to salespeople who do most of their business via an organization and the best practices for CFOs. Tune in to learn more about selling when no one is buying.

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 succeed in today's competitive sales environment. They further discuss how to improve customer retention in a business and win over investors. Tune in to learn more about selling when no one is buying.

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 can help you to sell. Tune in now to hear all about selling during uncertain times.

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 Interest into Advocacy.” Tune in to learn how to convert a single interested stakeholder into an advocate for you among the broader buying team from interviews with Mor Assouline, Jeff Bajorek, Nate Nasralla, and Brandon Fluharty.

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 Rajani, and Doug Ferreira.

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 themes that have disrupted the status quo of selling this year.

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.

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.

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.

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 method, as well as the roles that early stakeholder engagement, discovery, and salesperson energy have in facilitating a successful sales process.

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.

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.

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.

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.

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 you.

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.

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.

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.

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.

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 SDRs and AEs to be successful in sales.

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, safety, or peace of mind. Hence, they are compelled to take action as quickly as possible.

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.

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 perplexing behaviors that occur when closing a sale. Belal shares his personal experiences in tactically managing those dysfunctional processes, including how he used reframe techniques to align solutions with clearly articulated company problems and how he built relationships with "champions," or internal trustees, to help demystify organizational complexity and further champion sales objectives.

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.

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 products and services to other stakeholders or potential customers.

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, effective, and beneficial.

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, and build long-term relationships by focusing on a customer's feelings rather than logic or the product's features.

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 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.

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.

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.

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.

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!

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.

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.

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, what if, with a thorough understanding of a niche's issue, one could engage an audience in a substantive discussion, leading to meaningful interaction, resulting in genuine value to a customer? Amy goes into great detail about the impact of short-term approaches on sales outcomes.

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 customers connect with stories, especially ones that highlight challenges they are facing and how you have enabled better outcomes for other customers like them.

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.

In 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.

In 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 seller to develop compelling insights through other sensitive factors that influence success.

In 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.

In 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 unpack what high-performing sellers do differently than their average or core performers peers when it comes to handling curveballs that are thrown their way in late-stage negotiations.

Does 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.

Insight-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.

On 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.

On 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.

How 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.

Have 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.

On 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. 

On 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 Jaramillo, Founder and President of Personal ABM will be talking all how you can build credibility with social selling techniques. 

On 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.