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

In 2020, around 306 billion emails were sent and received each day globally. This number is expected to rise to 376 billion emails per day by 2025. In this episode, Jake emphasizes the necessity of understanding and segmenting audiences meticulously, crafting messages that strike a balance between templatization and customization, and utilizing a multi-channel approach to cut through the noise. He underscores the importance of ongoing testing and adjustments to optimize outbound strategies effectively. Jake stresses that genuine customization and relevancy in messaging, tailored to the specific needs and jargon of the industry, are key to making an impact and not just adding to the clutter.

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If you use Outreach, you need Performance Pulse: https://skaled.com/services/performance-pulse/

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What will it take to innovate your sales organization for the modern buyer and consistently stay at the forefront with technology and AI?

Order your copy of the book and join The Innovative Seller Community:

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

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

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DM or book time with Jake to discuss your current sales processes and best practices: https://savvycal.com/Jake-Dunlap/innovative-seller-live

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

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

AI Sales Accelerator Workshops: https://skaled.com/insights/ai-sales-accelerator/

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

Workshop + Prompt Pro: https://bit.ly/accelerator-and-prompt-pro

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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

______________________________________________

Follow Jake:

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

Instagram: https://instagram.com/jake_dunlap_

Twitter: https://twitter.com/jaketdunlap

Website: https://jakedunlap.com

A staggering 81% of sales professionals are not meeting their outbound targets. Addressing this issue, Jake emphasizes the necessity of shifting from traditional quarterly optimization to a dynamic, bi-weekly process, potentially increasing results by 25%. He advocates for measuring meaningful sales activities—conversion rates and pipeline coverage—over mere volume, and introduces tools like "Performance Pulse" from Skaled for faster, data-driven optimizations. Next week’s episode will explore hyper-customization in outbound strategies to further enhance engagement and conversion rates.

______________________________________________

What will it take to innovate your sales organization for the modern buyer and consistently stay at the forefront with technology and AI?

Order your copy of the book and join The Innovative Seller Community:

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

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

______________________________________________

DM or book time with Jake to discuss your current sales processes and best practices: https://savvycal.com/Jake-Dunlap/innovative-seller-live

______________________________________________

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

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

AI Sales Accelerator Workshops: https://skaled.com/insights/ai-sales-accelerator/

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

Workshop + Prompt Pro: https://bit.ly/accelerator-and-prompt-pro

______________________________________________

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

______________________________________________

Follow Jake:

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

Instagram: https://instagram.com/jake_dunlap_

Twitter: https://twitter.com/jaketdunlap

Website: https://jakedunlap.com