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 the following week for a demo. You hang up and wait some more, with very little knowledge to sway you...
Jul 06, 2023•34 min•Ep. 77
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 is worth more than the cost-savings of discount oil, and you’ll be hard-pressed to find anyone that ...
Jun 29, 2023•28 min•Ep. 76
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 close our eyes, we are bombarded with endless information. So much so, much of it has become white noi...
Jun 15, 2023•24 min•Ep. 75
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 Challenger Sale podcast, we talk with Collin Mitchell , VP of Sales at Leadium about what it takes t...
Jun 06, 2023•30 min•Ep. 74
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 competitor is.” Yep, you read that right. You can’t sell something you don’t believe in… at least not very ...
May 30, 2023•22 min•Ep. 73
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 personality flaw—it’s just human nature. And according to Hannah Ajikawo , CEO and Founder of Revenue Fun...
May 23, 2023•33 min•Ep. 72
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 close this gap when we can’t even gauge how many light-years away our ICP is? According to our latest ...
May 16, 2023•32 min•Ep. 71
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 and our guest on the Winning The Challenger Sale podcast this week, is a former seller himself and a ...
May 09, 2023•32 min•Ep. 70
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 gym. Find out their favorite coffee shop. Heck, move in next door! (Okay, maybe this metaphor is gett...
May 02, 2023•34 min•Ep. 69
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 one of the best platforms available to add that extra value. If your commercial organization isn’t p...
Apr 25, 2023•29 min•Ep. 68
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 Sale, we speak with Chris Walker , CEO of Refine Labs , who, as a pioneer of dark social, explains jus...
Apr 18, 2023•41 min•Ep. 67
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 the noise and form meaningful connections with your audience, and ultimately, your buyers. When you...
Apr 11, 2023•28 min•Ep. 66
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 Challenger Sale podcast this week gives us the foundational elements of that “right way” to enable you t...
Apr 04, 2023•37 min
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 episode, we’re speaking with Michael Schaumberge r, who is both a Principal Executive Advisor and t...
Mar 28, 2023•30 min•Ep. 64
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' Club of Chicago , who reminds us of a commonly underutilized tactic for unlocking business potential: u...
Mar 21, 2023•35 min•Ep. 63
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. Little to no communication. And the longer they go without a wheel alignment, the costlier that mi...
Mar 15, 2023•33 min•Ep. 62
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 episode, we speak with Lori Richardson , CEO and Founder of Score More Sales , about her career-long advoc...
Mar 07, 2023•33 min•Ep. 61
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 Monroe Partners , for a discussion on how to navigate economic uncertainty in a way that actually dr...
Feb 28, 2023•30 min•Ep. 60
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 wh...
Feb 21, 2023•23 min•Ep. 59
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...
Feb 14, 2023•24 min•Ep. 58
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.
Feb 07, 2023•26 min•Ep. 57
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 ...
Jan 24, 2023•22 min•Ep. 56
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.
Jan 10, 2023•20 min•Ep. 55
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.
Dec 20, 2022•32 min•Ep. 54
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.
Dec 13, 2022•20 min•Ep. 53
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.
Dec 06, 2022•40 min•Ep. 52
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.
Nov 29, 2022•44 min•Ep. 51
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.
Nov 22, 2022•24 min•Ep. 50
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.
Nov 15, 2022•34 min•Ep. 49
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.
Nov 08, 2022•42 min•Ep. 48
