Winning the Challenger Sale

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 foster growth and success in today’s sales leader...

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 of Personal ABM , argues that this team approach...

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 through the turbulent pandemic era, the cost of ina...

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 final mile and what they can do in 2024 to improv...

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 year, the top 20% of sales professionals will ha...

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 impact on your win rates. Ted and Andee address...

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 what to expect as the sales world continues to evolv...

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, CEO of Challenger, celebrates this milestone epis...

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 collaboration and insight to navigate today’s evolving b...

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 Sales Gravy , joins Andee this week to discuss avoi...

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, Andee is joined by former NFL player turned sales lea...

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 the Andee this week to discuss all things necess...

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 trust with customers is essential for the future — ye...

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 veteran and VP of international sales at Challenger. M...

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 shares her remarkable journey from being a middle...

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 status of a profitable, valuable, growth-oriented...

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 onboarding, and support against the customer jour...

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 theme that can be used as a rallying cry, then...

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 with your SKO. Our guest, Lisa Earle McLeod , fou...

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 the advantages of virtual and hybrid events with th...

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, commitment, and movement around action items. Pau...

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 the course of 18 months, which they turned into...

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 you the results you’re looking for. In fact, most bl...

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 Consultant & Freelancer Marketer at Evan Patterson Co...

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 strengths. By intentionally welcoming diverse voices i...