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Winning the Challenger Sale

Challenger

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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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The sales profession has evolved, but one thing has remained the same: the power and importance of mentorship. Where sales leaders once learned in person from each other in unstructured meetings — office banter, going to lunch, connecting at conferences or networking events — many of today’s professionals now work primarily from home. So how can we…
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What does account-based marketing (ABM) look like in 2024? For most people, they talk about it as a platform, and not a strategy. When you embrace ABM as a critical part of your GTM strategy, you can break down internal barriers and bring marketing, sales and customer together to create the ultimate account experience. Kristina Jaramillo, president…
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For sellers, the past few years have shown that feast or famine, repeatable and dependable sales process wins every time. Kendra Tucker, CEO at Truckstop, joins Challenger CEO Andee Harris on this episode to talk about what she’s learned from her experience in private equity and as a sales leader. Kendra talks about how process guided Truckstop thr…
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You know your conversion rates, historical conversion rates, and territory inside and out. You have more data at your fingertips than ever before and your buyers keep saying yes — but then they don’t sign (or worse, disappear.). As sales leaders look back at 2023, many of them find themselves asking where things went wrong with customers during the…
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2024 promises more obstacles than ever for sellers, with increasingly elongated sales cycles, creeping increased indecision and tighter budgets. But what exactly does that mean for you and your sales team? Despite this bleak outlook, Matt Doyon, co-founder and CEO of Triple Session and author of “Revenue Revolution,” has a striking forecast: this y…
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Why aren’t you winning? For so many modern sellers, the answer is only visible once it’s too late. According to research published in The JOLT Effect, 40-60% of deals are lost to this nearly-invisible force. This week on WTCS we’re joined by Ted McKenna, founding partner at DCM Insights and co-author of The JOLT Effect, to break down indecision’s i…
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Throughout 2023, businesses experienced tightening budgets, layoffs, increasing numbers of stakeholders, longer deal cycles — yet expectations remain as high as ever. Nader Pishdad, principal executive advisor at Challenger, joins Challenger CEO Andee Harris to dive into trendand hypotheses for the coming year from both buyers and sellers — and wha…
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In this special 100th episode of Winning The Challenger Sale podcast, we’re joined by Ramsey Jay, Jr., Principal at Ramsey Jay, Jr. and Associates and co-author of The Mentorship Engine, who shares how to shift sales teams’ mindsets and build successful, optimized workplace cultures to supercharge sales teams heading into 2024. Host Andee Harris, C…
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What makes an efficient and successful modern selling machine? Customized, personalized tactics aligned directly to the customer journey. Alice Heiman, founder and “chief sales energizer” at Sales Strategies for CEOs has helped countless CEOs shift their mindset from traditional methods to a modernized approach — leading the way with strong collabo…
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What marks the difference between a prepared seller and an unprepared rep? Whichever one follows the fundamentals of sales during times of ease will be the one who successfully navigates volatile markets. Intentionality, strategy, discovery — remember those cornerstones and your sales team will rise above any coming adversity. Jeb Blount, CEO at Sa…
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Does AI hold the key to your end-of-year success? What are the effective ways that organizations are using it to drive results? Explore the role of AI in sales strategy, from identifying in-market accounts to streamlining processes, and discover innovative prospecting tactics that drive success, even in these challenging times. In this episode, And…
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What’s the key to creating end-of-year momentum? Creating the best buyer experience, prioritizing the right deals, and implementing feedback. Invest in these three strategies, and your sales team will optimize their performance in the final weeks of 2023 and launch into the new year with confidence. Sam Senior, co-founder and CEO at Testbox, joins …
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Think of your sales pipeline as less like a funnel and more like a subway map — your sellers can take multiple routes to close, as long as they head in the right general direction. It’s up to you to identify each customer’s unique journey — and that can’t be done without explicit efforts to foster relationships and customer-led growth. Building tru…
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Today’s market is complex and unpredictable, but one thing is certain — retention matters more now than ever before. By embracing the role of a trusted advisor and focusing on overall profitability over top-line growth, sales leaders can navigate the rollercoaster days ahead. In this episode, Andee Harris sits down with Marinus Maris, industry vete…
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How can sales leaders become trusted advisors and overcome the challenges of an elongated sales process while accounting for ever-evolving buyer behavior? In this episode of Winning The Challenger Sale, Krysten Conner shares effective strategies for building strong client relationships and solutions that drive retention and account growth. Krysten …
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80% of your revenue comes from 20% of your customer base, and retaining those customers comes at a fraction of the price of acquiring new ones. Yet, many sales and marketing efforts are still locked on closing new leads with metric-centric objectives. While new customers will always be essential for growth, retention is the only way to achieve the …
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What’s the top predictor of customer loyalty? It’s not service. It’s not even a great product (although that doesn’t hurt). It’s an exceptional sales experience — and that only happens when you bring all of the elements of the customer experience together, from product to marketing. And when you align sales, marketing, customer experience, customer…
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Here’s a controversial idea: Your SKO is not a massive training event. According to Peter Zink, Senior Director of Revenue Enablement at Sprout Social, it’s a time for people to come together, see each other, celebrate and align on a few critical concepts to take into the new year. To build an effective SKO today, Peter argues that you begin with a…
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When you speak with a client, do they think you’re there to help them, or to drive them to a close? Because buyers can tell. They hunger for sellers who deliver insights that support their goals and their business — and not a pop-in with bagels and coffee. The most effective sellers understand that they need to sell with purpose — and It all starts…
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Q4 will be here before you know it — and right after those three months of excitement comes the sales kickoff. And if you want to make sure your SKO brings your sellers together and sends them into 2024 with clarity and purpose, now is the time to begin planning it. Covid continues to impact the SKO planning process, as many organizations balance t…
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With weeks of prep work, exciting itineraries, and top-notch speakers, SKOs are usually an epicenter of excitement after a grueling end-of-year rush. But despite the traditional approach to designing SKOs as a rallying cry for motivation, they truly serve two main purposes: resetting and refocusing the team by providing clarity and creating energy,…
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A seller’s greatest enemy? It’s not “no.” It’s “We’ll see.” The average seller loses between 40% and 60% of their qualified pipeline to no decision. Matt Dixon, founding partner of DCM Insights and co-author of The Challenger Sale, The Effortless Experience, and The Challenger Customer. Matt and his co-author analyzed 2.4 million sales calls over t…
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Diversity, equity, inclusion, and belonging are simple—but getting it right is not easy. Creating a truly inclusive environment where your sales team reflects the diverse pipeline you have (or hope to build) requires a high level of intentionality. You can’t build an inclusive environment with just one initiative. A quarterly workshop won’t give yo…
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Game up on one screen, Discord on the other, thousands of people are connecting with one another at any given moment. Whether you like dodging red shells and drifting across iterations of rainbow road or you have an interest in specialized aircraft simulation, there’s an online community and gaming system for you. Evan Patterson, Marketing Consulta…
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Sales leaders, let’s try an exercise: if given a blank sheet of paper, can you write down three “superpowers” for each of your reps? The best sales leaders aren’t those who force reps to sell like them. Sales teams that consistently win lean into diversity through supportive leadership that enables psychological safety and amplifies individual stre…
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We’ve all heard that culture eats strategy for breakfast. But how can sales teams nurture a stronger culture among individual sellers? Start with mindset. Changing the way your organization sees its sellers—and the way those sellers see themselves—can unlock impressive sales growth. Our guest Catherine Brown, Founder of ExtraBold Sales, shares how …
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Sales teams now see sales tech like Gong and Showpad as staples for high-performing organizations. But these platforms are just the beginning. Fringe tech, enabled by AI and cross-platform collaboration, can automate and streamline administrative tasks, freeing up your sales team to invest in, you know, selling. The robots aren’t coming for your sa…
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Over the past few years, there have been astounding advancements in tech with no sign of slowing down—and we all have a choice to make: Terminator or Iron Man. As a sales leader (or any type of business leader, really), you have two options. You can choose to treat these innovations as a threat, run away and hide from technology, automation, and AI…
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You're marching into battle, armored allies by your side. Together, you have to decide how to reign as champion, but to do that you have to share your knowledge. How much do you give away without revealing your biggest strategic strengths (and weaknesses)? After all, your ally in battle may also be your competition in other realms of life. Like all…
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Truth bomb 💣 A lot of sellers fail because they fail to follow up. Your outbound can be on point, but unless it’s absolutely phenomenal, you’re not likely to close many deals with a single email. You’ve got to come back a few times, remind your buyer who you are, and show them exactly why they should execute your CTA. And guess what—tech can help w…
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You’ve identified a problem you want to solve for your organization. You’ve done the research and narrowed it down to two promising solutions. After visiting the websites for both, you click ‘book a call’ and wait. The first SDR spends an hour talking to you about our organization and needs—it sounds like you’re a great fit, at least from their per…
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You rely on the school bus to get your child to and from school safely every single day. You expect the bus to be outfitted with the best, most reliable parts and fuel. So how would you feel if your child was unexpectedly late coming home? And more—you found out the bus broke down because it was using cheap engine oil that causes higher ash buildup…
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Your alarm goes off and you grab your phone, silencing the noise to scroll social media for a few minutes before getting ready for the day. You stream music and eat breakfast—flipping through recipes and meal plans (paper or digital, be real) and planning your grocery list. You hop in the car and head to work or the gym or wherever you start your d…
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Sales has long been in fierce competition with other sellers and the status quo, losing customers to other companies and inaction. But today, we’re also up against every department head across our prospect’s businesses. With everyone lobbying for a slice of the budget, if the problem you solve isn’t a top priority in your prospect’s business today,…
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When it comes to winning with today’s B2B buyers, our guest on the Winning The Challenger Sale podcast this week has some serious mic-dropping comments: “If it’s not solving a problem, it’s a non-starter.” “If it's a great product, but there's not a great story to tell behind it, there's no point in really even selling it.” “Buyers can tell when yo…
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Your phone charger is frayed and bent. Wires exposed, you twist it slightly to the right and balance your phone just so to get it to charge. A new cord has been on your list for weeks, but let’s be honest, the situation isn’t quite urgent enough for you to hit “buy now.” It’s still charging, isn’t it? Until it isn’t. This strange habit of putting s…
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We think we know our customers… but what if they’re in an entirely different universe than we imagine? Each layer of customer understanding unveils a new truth that should ultimately shape how sales and marketing connect with buyers. But too often, there is a complete disconnect between what a customer knows about your product and what your sellers…
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Would you show up to a street race with a bicycle? That’s probably what it feels like as a seller up against today’s digitally-enabled buyers. B2B buyers have almost everything they need to make informed buying decisions on their own. They’re in the driver’s seat… and sellers are stuck pedaling behind, trying to catch up. Luckily, it doesn’t have t…
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Imagine your buyers all live in a gated community. A cold call is like showing up to the gatehouse without an invitation and expecting the security guard to let you in. But the buyer moved into that neighborhood for a reason, and it definitely wasn’t so that SDRs could show up unannounced. Instead, you need to get to know your buyers to turn that c…
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The bar has been raised for sellers and feels like it keeps rising. The amount of information modern buyers have is at an all-time high, buyers’ expectations from sellers have grown and changed, meaning sellers must now add more value than ever to help buyers along their purchasing journey. According to our latest guest, Ryan Barretto, President of…
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Word-of-mouth has long fueled the success of countless companies, big and small. But over the past several years, through the rise of the digital age, word-of-mouth has evolved into something with unlimited potential — something known as dark social. Now, a recommendation (or negative feedback) can reach millions with a single click of a ‘share’ bu…
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Social selling is the key to engaging with your buyers before they’re interested in talking to sales, before they’re even in the market for your solution. But what’s the key to successful social selling? Authenticity. Forget the “algorithm hacks.” Forget engagement for engagement’s sake. Showing up as your authentic self on social is what truly mat…
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Buying and selling have always been social activities. Except nowadays, most of that socializing happens digitally and in virtual networking spaces. What we’ve learned through the rise of social media platforms is that there’s a right way to approach your presence on social that will help you form real connections and have meaningful conversations …
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Sales and marketing have perhaps the most well-known tension since cats and dogs—only, it’s far more important that they get along. Short of couples therapy or family counseling (which will make more sense once you listen to the episode), how do you cut the tension between these teams and create a symbiotic relationship leading to stronger sales me…
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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…
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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…
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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…
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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…
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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 …
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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…
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