Winning the Challenger Sale

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 managers can begin shifting away from the stereo...

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 sales team — but they are coming to help. Embracing...

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 as if they are the Terminator, out for your job a...

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 allies on a battlefield, business partners must navig...

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 without scaring prospects away with a robotic tone...

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 perspective. So they schedule another call with you t...

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 over the premium option. Your child's well-being...

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 day. From the moment we wake up to the moment we cl...

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, you won’t close a sale. In Ep. 74 of Winning the...

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 you're not as into the product as maybe your competi...

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 something off until it’s truly broken isn’t a perso...

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 are communicating to the market. So how can we cl...

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 to be this way. Hendrik Isebaert , CEO at Showpad a...

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 cold call into a warm call. Bump into them at the g...

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 Sprout Social , social media has quickly become...

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’ button. On this episode of Winning the Challenger Sa...

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 matters because that’s what will help you cut through...

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 with buyers. And our guest on the Winning The Chal...

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 messaging that consistently wins over buyers In this...

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 Director, President, and CEO at The Executives'​ Clu...

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 opposite directions. Different goals. Different metrics...

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 that would strengthen your business. In this episod...

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 Kocher , Director of Business Development at West...

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 in...

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. The...