Winning the Challenger Sale

Feb 27 2024 26

Winning the Challenger Sale Podcast artwork

Win the sales moments that matter, every day. Take a deep dive into the day-to-day skills and behaviors proven to win in complex selling and buying environments. Hosted by the team that brought you the best-selling books, "The Challenger Sale" and "The Challenger Customer."

Learn more about our "Winning the Challenger Sale" webinar series here: https://www.challengerinc.com/events/

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#107: Mentoring the Next Generation of Successful Sales Leaders

Feb 27 2024 40 mins

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 i

#106: Accelerating Pipeline with a Unified ABM Strategy

Feb 13 2024 25 mins

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

#105: Balancing the Art and Science of Selling

Jan 30 2024 32 mins

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,

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

Jan 23 2024 34 mins

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

#103: Positive Paranoia with Matt Doyon

Jan 16 2024 30 mins

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 profe

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

Jan 09 2024 32 mins

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. T

#101: Insights from the Frontline at Challenger

Dec 19 2023 23 mins

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

#100: Can You Actually be Authentic at Work?

Dec 12 2023 30 mins

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 th

#99: Orchestrating Success in Q4

Nov 28 2023 33 mins

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 naviga

#98: Closing Complex Deals in a Changing Economic Landscape

Nov 20 2023 28 mins

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