Winning the Challenger Sale

#107: Mentoring the Next Generation of Successful Sales Leaders

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

#106: Accelerating Pipeline with a Unified ABM Strategy

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 p

#105: Balancing the Art and Science of Selling

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 Challen

#104: How Challengers Thrive in a Fear-Driven Market

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 say

#103: Positive Paranoia with Matt Doyon

2024 promises more obstacles than ever for sellers, with increasingly elongated sales cycles, creeping increased indecision and tighter budgets. But what exactly does tha

#102: From Stalled to Sealed: Winning Sales Strategies For Today

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

#101: Insights from the Frontline at Challenger

Throughout 2023, businesses experienced tightening budgets, layoffs, increasing numbers of stakeholders, longer deal cycles — yet expectations remain as high as ever. N

#100: Can You Actually be Authentic at Work?

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 Me

#99: Orchestrating Success in Q4

What makes an efficient and successful modern selling machine? Customized, personalized tactics aligned directly to the customer journey. Alice Heiman, founder and “chi

#98: Closing Complex Deals in a Changing Economic Landscape

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 succes

#97: Tackling Q4: Sales Strategies from an NFL Pro Turned Sales Leader

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,

#96: Seal the Deal with Customer-Centric Experiences

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 strate

#95: Customer Messaging that Seals the Deal

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

#94: Want Account Growth? Make Your Business Indispensable

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 focusi

#93: From Lost to Loyalty: Navigating the Path to Account Growth

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 episod

#92: B2B Growth in the Self-Serve Era

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 market

#91: Expand like You Land: Account Growth Strategies that Work

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 t

#90: Maintain the Momentum with the Right SKO Theme

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

#89: The Power of a Purpose-Driven SKO

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

#88: A Practical Guide to Creating a Kick-Ass SKO

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 t