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Ryan Staley on Leveraging AI, turning lows into highs & the no.1 component sales leaders neglect in closing enterprise deals

Ryan Staley

Ryan Staley

Founder & CEO of Whale Boss & Podcast Host of The Scale Up Show
Whale Boss
Ryan has over 20 years of software & service selling experience. From having senior sales consultant roles in the early 2000s at companies like Marcus Evans & Pitney Bowes, to heading up strategic accounts as a VP at Flex Technology Group in 2018, Ryan has vast experience in scaling sales organizations, specifically enterprise.
Ryan is also a founding member in globally recognised sales communities, RevGenius & Sales Hacker.
As an active member in the GTM community, he has also taught over 800 VP of sales & CROs for enterprise sales & GTM, as part of pavilion’s CRO/Enterprise sales school - something he continues to do today.
Most recently, Ryan uses his knowledge to help other saas founders & revenue leaders unlock high ACV growth & potential with his consultancy firm, Whale Boss. Simultaneously, Ryan is the Host of The Scale up Show - a podcast dedicated to breaking down the mindsets behind top SaaS CEO’s & how they’ve built their companies repeatedly & predictably.


Understand the blockers in your sales process & spend time to close
Build trust and mutually align with your buyers
Stop wasting time on deals that end in no decision
Discover & engage large buying teams
Forecast with certainty
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