EP. 5

EP. 5

How Enterprise Views Buying AI Products

How Enterprise Views Buying AI Products

Jan 28, 2026

36 minutes

The conversation delves into the challenges of managing multiple stakeholders in enterprise sales, with a focus on the transition from a restaurant franchise to a sales career. It explores the lessons learned from the restaurant business and ad sales, comparing ad tech sales with SaaS sales. The discussion also covers the sales process and challenges in selling True Rating, including the ROI pitch and objections. Additionally, it highlights the data-driven play and the approach to handling objections in the sales process. The conversation covers the importance of balancing storytelling and data in sales pitches, as well as the challenges and strategies for stakeholder management and alignment in complex deals. Takeaways Managing multiple stakeholders in enterprise sales Transition from restaurant franchise to sales career Storytelling vs. Data Stakeholder Management Chapters 00:00 Introduction to Managing Multiple Stakeholders in Enterprise Sales 05:43 Comparison of Ad Tech Sales and SaaS Sales 13:39 ROI Pitch and Objections in Sales Process 18:50 Data-Driven Play and Handling Objections

The conversation delves into the challenges of managing multiple stakeholders in enterprise sales, with a focus on the transition from a restaurant franchise to a sales career. It explores the lessons learned from the restaurant business and ad sales, comparing ad tech sales with SaaS sales. The discussion also covers the sales process and challenges in selling True Rating, including the ROI pitch and objections. Additionally, it highlights the data-driven play and the approach to handling objections in the sales process. The conversation covers the importance of balancing storytelling and data in sales pitches, as well as the challenges and strategies for stakeholder management and alignment in complex deals. Takeaways Managing multiple stakeholders in enterprise sales Transition from restaurant franchise to sales career Storytelling vs. Data Stakeholder Management Chapters 00:00 Introduction to Managing Multiple Stakeholders in Enterprise Sales 05:43 Comparison of Ad Tech Sales and SaaS Sales 13:39 ROI Pitch and Objections in Sales Process 18:50 Data-Driven Play and Handling Objections

Guests:

Guests:

Dan Morgenstern

Dan Morgenstern

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Episode Summary

Episode Summary

Dan Morgenstern went from co-founding a restaurant franchise to leading enterprise sales at TrueRating, where he navigates 12-18 month deals selling customer feedback software to major retailers. In this episode, Dan shares the painful lesson he learned from rewatching a call recording—cutting off a prospect mid-sentence cost him the deal—and explains why giving buyers space to tell their story matters more than getting through your slides.

We dig into the mechanics of managing five or six stakeholders across operations, CX, and IT teams, and how Dan uses ChatGPT to prep for calls by analyzing earnings transcripts and mapping insights to each group's priorities. Dan also shares a compelling story about a grocer whose "reduce spoilage" initiative was actually destroying their evening sales—discovered only because TrueRating captured feedback from the majority of customers, not just the angry few.

The conversation closes with Dan's take on AI fatigue at NRF: buyers are tired of "AI-adjacent" claims and want to see real innovation that solves actual problems.