
Winning the Challenger Sale
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/
Latest episodes

Feb 7, 2023 • 26min
#57 Being a human first and selling through storytelling to win in uncertain times with Rebecca Grimes, CRO at Ruby
On this episode of the Winning the Challenger Sale podcast, Andee Harris, CEO of Challenger, is joined by Rebecca Grimes, Chief Revenue Officer at Ruby, to discuss skills such as listening skills, storytelling skills and others that are necessary to possess for sales when the market is tough. They also discuss how agility and being a human first can help you to sell. Tune in now to hear all about selling during uncertain times.

Jan 24, 2023 • 22min
#56 Turning Interest Into Advocacy: Episode Recap With Andee Harris, CEO of Challenger
On this episode of the Winning the Challenger Sale podcast, Andee Harris, CEO of Challenger, recaps highlights from the second most popular theme from the podcast last year. The goal is to help you kickstart the year on a solid foundation while riding on the wings of these clips. This time, she walks us through deep insights from the theme “Turning Interest into Advocacy.” Tune in to learn how to convert a single interested stakeholder into an advocate for you among the broader buying team from interviews with Mor Assouline, Jeff Bajorek, Nate Nasralla, and Brandon Fluharty.

Jan 10, 2023 • 20min
#55 Persuasive Storytelling: Episode Recap With Andee Harris, CEO of Challenger
On this episode of the Winning the Challenger Sale podcast, our host Andee Harris, CEO of Challenger, runs through the highlights of our most popular theme from 2022. Tune in to hear non-traditional ideas on effectively deploying storytelling to inspire action and solve your customer’s problem from interviews with Brett Adamson, Nick Capozzi, Ravi Rajani, and Doug Ferreira.

16 snips
Dec 20, 2022 • 32min
#54 2022 Year in Review With Andee Harris, CEO of Challenger
On this special 2022 Year in Review episode of the Winning the Challenger Sale podcast, our new host Andee Harris, CEO of Challenger, runs through the highlights of our most popular episodes from this year. Tune in to hear the best clips from Ravi Rajani, Brandon Fluharty, Jeff Bajorek, Sam McKenna, Will Allred, and Tom Alaimo as they discuss major themes that have disrupted the status quo of selling this year.

Dec 13, 2022 • 20min
#53 The 2022 Year-in-Review With Andee Harris, CEO of Challenger
The theme for December on Winning the Challenger Sale is a recap of the best insights from 2022. WTCS host, Jen Allen, speaks with Andee Harris, CEO of Challenger, to explore the major themes that have disrupted the status quo of selling this year.

Dec 6, 2022 • 40min
#52 The 2022 Year-in-Review With Dr. Howard Dover, Director of the Center for Professional Sales and Sales Coaching at Naveen Jindal School
The theme for December on Winning the Challenger Sale is a recap of the best insights from 2022. WTCS host, Jen Allen, is joined by Dr. Howard Dover to explore the major themes that have disrupted the status quo of selling this year.

14 snips
Nov 29, 2022 • 44min
#51 Avoiding Death by Discovery with Doug Landis, Growth Partner at Emergence Capital
The theme for this special episode on Winning the Challenger Sale is Avoiding Death by Discovery. WTCS host, Jen Allen, is joined by Doug Landis to explore the major themes, such as “anti-discovery,” that disrupted the status quo of selling throughout the year 2022.

Nov 22, 2022 • 24min
#50 Preparing for Negotiations with Caroline Franczia, Founder at Uppercut First
The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host, Jen Allen, is joined by Caroline Franczia to explore how star sellers prepare negotiables and anticipate curve balls ahead of negotiation conversations. In addition, they discuss the similarities and differences between MEDDIC and the Challenger selling method, as well as the roles that early stakeholder engagement, discovery, and salesperson energy have in facilitating a successful sales process.

Nov 15, 2022 • 34min
#49 Preparing for Negotiations with Kyle Asay, Regional Vice President, Corporate Sales at MongoDB
The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host, Jen Allen, is joined by Kyle Asay to discuss how to prepare, anticipate, and mitigate curveballs ahead of negotiation conversations.

Nov 8, 2022 • 42min
#48 Preparing for Negotiations with Niko Papademetriou, Senior Vice President Sales & Business Development at Qu POS
The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host, Jen Allen, is joined by Niko Papademetriou to discuss techniques used by star salespeople to prepare for negotiations and any surprises that may come up.
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