Episode #49: Scaling Excellence Across Your Sales Organization - Kyle Asay
A systematic approach to sales leadership
As someone with marketing roots, I’ve always been fascinated by the role of the sales leader and the type of people who perform it.
The job is relentless. Each victory is temporary, giving way to the cold reality of fresh quota that needs to be hit. Every quarter is a new cycle of proving yourself.
Success is also black and white. You’ve either hit your number or you haven’t. The closed-won opportunity dashboard is not open to interpretation or debate.
Great sellers are built for this sort of challenge. My observation from working with such people is that they find a way. They play the long game, store up nuts for the winter, and are able to close deals that others can’t.
But what happens when you move from AE to leadership? Being a lone hero doesn’t work when you’re managing a team of sellers and are responsible for ALL their quotas.
Now our hypothetical sales leader—usually a top-performing individual contributor—must find a way to scale that type of success across dozens or hundreds of reps. The fact that average tenure for a VP Sales is a mere 19 months speaks to how difficult this task is.
Today’s guest, Kyle Asay, has made the jump from SDR to AE to sales leader successfully and explains how to achieve predictable execution across the team. We talk about how to scale sales excellence, balance standardization with creativity, and build trust and rapport at every stage of the sales process.
Kyle also shares his insights on navigating the transition from individual contributor to sales leader, the real role of AI in outbound, and how to build a side hustle while leading a team.
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About Today's Guest
Kyle Asay started his career in sales as an SDR at Qualtrics, where he qualified for five consecutive President’s Clubs as an AE, front-line leader, and second-line leader.
After an incredible 8.5 years at Qualtrics, he's gone on to serve as a sales leader for MongoDB and currently at LaunchDarkly.
You can also find him sharing his frameworks with over 10,000 sellers at Sales Introverts.
Key Topics
[00:00] - Introduction
[01:52] - Current selling environment
[04:46] - Scaling sales excellence
[10:05] - Right-sizing discovery phase
[12:39] - Building trust and rapport
[17:53] - Transitioning from sales IC to sales leader
[20:46] - The job of a sales leader
[24:10] - Identifying the right people
[27:47] - Standardized process vs. individual ingenuity
[30:59] - Handling the pressure of sales leadership
[34:55] - AEs and SDR alignment
[42:47] - AI SDRs
[44:59] - Sales and RevOps relationship
[48:23] - Building a side hustle
Thanks to Our Sponsor
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