From SMB to Enterprise Sales

Most agents get stuck competing for the same smal…

An episode of the Merchant Sales Podcast podcast, hosted by Merchant Sales Podcast, titled "From SMB to Enterprise Sales" was published on April 3, 2026 and runs 50 minutes.

April 3, 2026 ·50m · Merchant Sales Podcast

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Summary

Most agents get stuck competing for the same small accounts, fighting over price in crowded verticals like restaurants and retail. In this episode of the Merchant Sales Podcast, James sits down with Josh Holden to break down what it really takes to move upmarket—targeting larger businesses, focusing on specific verticals, and building a strategy that actually scales. They dive into hiring strategies, W2 vs 1099 models, building trust with bigger clients, and why shifting your focus can unlock higher-value deals and long-term growth. Plus, Today in Payments covers major industry updates including debanking concerns, cash acceptance laws, and the expansion of global payment platforms.

Episode Description

Most agents get stuck competing for the same small accounts, fighting over price in crowded verticals like restaurants and retail. In this episode of the Merchant Sales Podcast, James sits down with Josh Holden to break down what it really takes to move upmarket—targeting larger businesses, focusing on specific verticals, and building a strategy that actually scales. They dive into hiring strategies, W2 vs 1099 models, building trust with bigger clients, and why shifting your focus can unlock higher-value deals and long-term growth. Plus, Today in Payments covers major industry updates including debanking concerns, cash acceptance laws, and the expansion of global payment platforms.

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