Jake is joined by Bryan Caplin, CRO of Thoropass and a founding member of Pavilion, to discuss the intricacies of moving upmarket. With over 20 years of experience in leading and scaling high-performing revenue organizations, Bryan shares his insights on the common mistakes companies make when targeting mid-market and enterprise clients. They delve into the evolution of go-to-market strategies, the importance of cross-functional alignment, and the need for a dedicated approach to successfully transition from SMBs to larger markets. Bryan emphasizes the significance of planning, proper talent management, and the value of iterative learning in this complex but rewarding journey.

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Follow Bryan:

Connect with Bryan on LinkedIn: https://www.linkedin.com/in/bcaplin/

Check out Thoropass: https://thoropass.com/

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The Innovative Seller: https://www.jakedunlap.com/the-innovative-seller

• The Innovative Seller answers the question: what will it take to innovate your sales organization for the modern buyer and consistently stay at the forefront with technology and AI?

Community:

https://www.jakedunlap.com/the-innovative-seller-community

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AI Unleashed: https://bit.ly/ai-unleashed-series

AI Sales Prompt Pro: https://skaled.com/insights/ai-sales-prompt-pro/

Custom GPTs for Sales: https://skaled.com/insights/custom-gpts-for-sales/

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Book Time:

https://savvycal.com/Jake-Dunlap/modern-leader

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Sign up for the Modern Leader newsletter for more tips and talks from Jake:

Email: https://skaled.com/modern-leader-sign-up

LinkedIn: https://bit.ly/modern-leader-newsletter

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Follow Jake:

LinkedIn: https://linkedin.com/in/jakedunlap

Instagram: https://instagram.com/jake_dunlap_

Twitter: https://twitter.com/jaketdunlap

Website: https://jakedunlap.com