Episode 25: "Intestinal Fortitude" | Startup Sales Veteran Rob Balena on Vetting Enterprise Sales Strategy, Hiring a Great Sales Force, and Where Most Founders Get it Wrong

Today's episode explores three ideas that caught my attention: 

• Long ball is the name of the game - Can this company survive long enough to close a deal? Maybe they’ve closed some VC funding, but the risk-seeking VC buyer is VERY different from the risk-averse enterprise buyer. Proof in one does not serve as proof in another. 
• How is this company going to get great sellers to come sell for them? - This is not a guarantee. Can this founder convince the best salespeople that their thing is worth selling? The founder’s vision and mission is important, but it can’t be something to “over rotate” on, as it won’t get the sellers paid. 
• “Tell me the story of this logo.” - Details are gold. Generalities? Red flag. Sellers taking quick wins and shortcuts will not land enduring partnerships. Sellers taking the long, thoughtful, strategic route? Maybe they’ve got a shot. 

I explore these ideas and more with Rob Balena, Strategic Accounts at TeamSense. He brings extensive expertise in enterprise software sales, having successfully guided multiple venture-backed startups in selling to Fortune 500 companies. Currently leading sales at TeamSense, he combines deep experience in technical enterprise sales with a unique perspective on manufacturing technology adoption. His journey from founding a sales coaching practice to driving enterprise deals gives him valuable perspective into both the strategic and tactical elements of complex B2B sales.

During our conversation, Rob shares:

• A framework for evaluating startup-to-enterprise fit that challenges founders to think beyond their VC pitch and focus on risk mitigation for corporate buyers.
• Practical strategies for building credibility as a small company selling to large enterprises, including specific examples of leveraging customer success stories.
• Critical considerations for sales leadership roles at startups, including the balance between process creation and customer engagement.

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