Winning the Challenger Sale

Breaking down the theory of Challenger

Learn from sellers who execute the Challenger Sale every day.
Winning the Challenger Sale offers salespeople approachable recommendations to break down the theory of Challenger. All interviews, thought leaders, and the host are real sellers in the field successfully executing the Challenger Sale.

So many people out there know about The Challenger Sale book but STILL don’t know that the company Challenger exists. We created Winning the Challenger Sale to connect the dots between the book, the training, and the language of the modern buyer. Our podcasts, webinars, and thought leadership give sellers, frontline managers, and sales leaders the tactical, practical advice essential to winning the Challenger sale every day.

Hosted by

Andee Harris
Chief Executive Officer

Winning the Challenger Sale Podcast

Every Tuesday, join us for our sales podcast hosted by Andee Harris, Chief Executive Office. In each episode, Andee meets with special guests for insightful discussions around the topics featured in our Winning the Challenger Sale webinar series.

These bite-sized sales podcasts (average length: 30 to 40 minutes) are a great way to refresh your selling skills and learn new sales strategies that will help you deliver greater customer value.


Recent topics include:

Preparing for negotiations

Creating a mutual close plan

Driving urgency for change

Resolving buying group conflict

Turning interest into advocacy

Telling persuasive stories

Prioritizing sales opportunities

Avoiding email pitfalls

Turning social selling into a secret weapon

Engaging C-level buyers

Subscribe wherever you get your podcasts!

 Listen on Google Podcasts

Winning the Challenger Sale webinars

Every month, we host a webinar for sales professionals and commercial leaders on a Thursday starting at 11 AM ET. Each webinar opens up the Challenger playbook, sharing practical advice and actionable insights that will help you execute the skills and behaviors proven to win in complex selling and buying environments.

Winning the Challenger Sale: Season 3 Replay

Catch up on all of the episodes of Season 3, Winning the Challenger sale webinar series.

Read More

Winning the Challenger Sale: Season 3 Replay

Catch up on all of the episodes of Season 3, Winning the Challenger sale webinar series.

Read More

Sign up for the 2023 series

Register for the entire Winning the Challenger Sale Webinar Series to make 2023 your best year yet. And stay tuned for the announcement of topics for Season 4 of our Winning the Challenger Sale webinar.

Once you register, you’ll receive a Zoom calendar invite for each session.

If you’ve missed an episode, catch up on replays of our past webinars.

Recent webinars have tackled sales topics including these:

Negotiating with late-stage stakeholders

Building instant credibility with new customers and prospects

Adding value with high-gain questions during discovery

Earning the right to teach customers

Prioritizing pursuits and protecting limited selling time

Articulating the value of your solutions

Building the business case for change

Leading group meetings and building consensus

Responding to tough customer objections

Handling negotiation curveballs

Winning the Challenger Sale: Season 3 Replay

Catch up on all of the episodes of Season 3, Winning the Challenger sale webinar series.

Read More

Winning the Challenger Sale: Season 2 Replay

Catch up on the 13 episodes of Series 2, Winning the Challenger sale.

Read More

Winning the Challenger Sale : Series 1 Replays

Catch up on the 7 episodes of Series 1, Winning the Challenger sale.

Read More

Winning the Challenger Sale Resources

Want to take a deeper dive into Challenger methodology?

Here is where you can check out our latest e-books, white papers, and resources to discover how organizations like yours are implementing Challenger sales skills and driving growth through exceptional customer experiences. It’s the best of our WTCS monthly topics from the podcast and webinar brought into one place for you to read, share, and absorb.

View resources

What people are saying about Winning the Challenger Sale


“This series is truly masterful.”

Executive Coach, PR Firm

“This series makes the intangible tangible.”

B2B Sales Thought Leader

“The topics in this series are excellent.”

Sales Director, Multibillion-Dollar IT & Services Company

“These sessions are excellent for learning tactical ways to implement the Challenger philosophy. The Negotiation session was extremely helpful.”

Chief Learning Officer, Insurance Company

“This was the TIGHTEST webinar I have attended in a year of webinars. From a content, marketing, and production perspective, the Challenger team is clearly running a tight ship with all the boxes checked.”

Business Development & Marketing Professional, Legal Services Company