Selling Enterprise AI with Context, Adoption, and Measurable ROI with Daniel Simon

Episode notes

Enterprise AI buying has moved quickly, but durable adoption still depends on context, security, workflow fit, and measurable business impact. Daniel Simon, Enterprise Account Executive at Glean, joins John Kaplan and John McMahon to discuss what it takes to sell AI in complex enterprise environments, why multi-threading matters more when buyers are evaluating broad organizational change, and how strong sellers build trust by tying use cases to productivity, governance, and ROI instead of relying on product excitement alone. Daniel Simon is an Enterprise Account Executive at Glean, where he works with large enterprises on AI adoption, knowledge discovery, and productivity across complex organizations. He brings experience selling enterprise technology into multi-stakeholder buying environments.

• The Hidden Cost of False Velocity with Randy Riemersma69 / 100
• AI Is Redefining Seller Productivity with Alex Varel
• How Revenue Leaders Scale Beyond Hero Sellers with Jason Forget, CRO Behind Multiple Startup-to-Scale Journeys
• You Can’t Delegate Sales Early with Lou Shipley
• High LTV Isn’t Enough: The ICP Tradeoff Leaders Miss with Dan Sperring