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20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

Shownote

John McMahon is widely regarded as one of the greatest enterprise-software sales leaders of all time. He's the only person to have served as Chief Revenue Officer at five public software companies: PTC, GeoTel, Ariba, BladeLogic and BMC Software. He helped...

Highlights

John McMahon, a legendary figure in enterprise software sales, brings decades of experience from leading revenue at five public companies and advising high-growth tech firms like Snowflake and MongoDB. In this conversation, he unpacks the enduring principles of sales leadership while addressing how modern shifts—such as AI, remote work, and product-led growth—are reshaping the landscape.
04:29
The shift to consumption-based software reduces time to deliver value, demanding faster customer success.
10:17
Losing a deal often results from skipping a critical step in the sales process.
14:16
Discounting isn't the best way to create urgency; aligning on pain and consequences is more effective.
23:09
The most important non-natural skill in sales is listening with the intent to understand.
38:20
Hiring too many reps too quickly creates a bad sales culture
49:54
Children don't have to suffer to be strong; they can teach you new ways of growing.
59:48
The worst deals were made in 2021 during remote investing.

Chapters

John McMahon on Enterprise Sales Leadership
00:00
The Art and Science of Sales: Insights from a Veteran
03:33
Adapting Sales Strategies in the Age of AI and PLG
04:29
The Ultimate Framework to do Deal Qualification
07:47
How to Drive Urgency and Maintain Sales Process
14:13
How to Hire the Best Sales Reps
20:06
Step-by-Step Guide to Training Sales Reps
25:11
The Mindset of the Best Sales Reps
45:22
Single Most Important Skill to Win in Sales
54:55

Transcript

Harry Stebbings: This is 20Sales with me, Harry Stebbings. Now, 20Sales is the monthly show where we sit down with the best sales leaders to unpack how they hire, train, and retain the best sales teams. Joining me is a legend, John McMahon, widely regarded...