From SMB to Enterprise Sales

About this episode

This episode discusses strategies for moving from small to enterprise sales, including hiring and building trust with larger clients.

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.

People in this episode

Host: James

Guest: Josh Holden

Topics covered

• SMB sales
• enterprise sales
• upmarket strategy
• hiring strategies
• client trust
• payment industry updates

Keywords

• SMB
• enterprise sales
• upmarket
• hiring strategies
• client trust
• payment platforms
• industry updates

Mentioned in this episode

Organizations: Merchant Sales Podcast, Today in Payments

More episodes of Merchant Sales Podcast

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• Building Business Value in the AI Era · June 5, 2026 · 55 min
• How Tap on Phone Is Changing Merchant Payments · May 29, 2026 · 37 min
• The PayFac Opportunity · May 22, 2026 · 50 min
• How Payment Processing Works · May 15, 2026 · 33 min
• How to Reduce Fraud Without Losing Sales · May 8, 2026 · 53 min