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 c

#106: Accelerating Pipeline with a Unified ABM Strategy

Feb 13th, 2024 25m 1s

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 marke

#105: Balancing the Art and Science of Selling

Jan 30th, 2024 32m 31s

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 h

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

Jan 23rd, 2024 34m 35s

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 leader

#103: Positive Paranoia with Matt Doyon

Jan 16th, 2024 30m 28s

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,

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

Jan 9th, 2024 32m 52s

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 Te

#101: Insights from the Frontline at Challenger

Dec 19th, 2023 23m 33s

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 C

#100: Can You Actually be Authentic at Work?

Dec 12th, 2023 30m 57s

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 s

#99: Orchestrating Success in Q4

Nov 28th, 2023 33m 14s

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 s

#98: Closing Complex Deals in a Changing Economic Landscape

Nov 21st, 2023 28m 22s

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 — r

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

Nov 14th, 2023 19m 23s

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 discove

#96: Seal the Deal with Customer-Centric Experiences

Nov 7th, 2023 27m 17s

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 wee

#95: Customer Messaging that Seals the Deal

Oct 31st, 2023 24m 5s

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

#94: Want Account Growth? Make Your Business Indispensable

Oct 24th, 2023 22m 13s

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 naviga

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

Oct 17th, 2023 24m 18s

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

#92: B2B Growth in the Self-Serve Era

Oct 10th, 2023 23m 18s

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 obje

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

Oct 3rd, 2023 26m 4s

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 experien

#90: Maintain the Momentum with the Right SKO Theme

Sep 26th, 2023 18m 1s

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 critic

#89: The Power of a Purpose-Driven SKO

Sep 19th, 2023 33m 23s

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

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

Sep 12th, 2023 20m 47s

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

#87: You Need a Chief Reminding Officer

Sep 5th, 2023 28m 59s

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 t

#86: From Radio Silence to YES: The JOLT Effect with Matt Dixon

Aug 31st, 2023 35m 25s

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 Effortle

#85: Beyond Lip Service: Building an Inclusive Sales Culture

Aug 29th, 2023 24m 50s

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 intentionali

#84: Activating Authenticity to Engage Stronger Social Sellers

Aug 22nd, 2023 30m 28s

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 airc

#83: Diversity Could Be Your Sales Culture's Superpower

Aug 15th, 2023 25m 53s

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 int