Podcast Episode

The ROI of Multi-Persona Selling with Daniel Simon

Revenue Builders

Aug 30, 202611 min

Who’s talking

5 speakers
Daniel Simon7 min · 69%
John Kaplan1 min · 12%
John McMahon1 min · 10%
Speaker 434 sec · 5%
Speaker 525 sec · 4%

1Transcript19 turns · 11 min

JK
John Kaplan0:00

[upbeat music] Welcome to the Revenue Builders, hosted by John Kaplan and Jon McMahon. In this clip, Daniel Simon from Glean breaks down what strong multithreading looks like in an enterprise AI deal. He walks through how he moved beyond the CTO and built use cases across product, engineering, finance, legal, and the AI program team. The point is simple: AI deals do not stick because one executive likes the idea. They stick when multiple people can connect the solution to their own workflow, their own path, and a measurable business case. For revenue leaders, this is a practical look at how to turn interest in AI into real internal demand. Let's dive in.

JM
John McMahon0:49

You know, you said there's a difference between being, and Johnny said, like a domain expertise in an application versus the ability to connect hundreds of applications, uh, and get that three sixty view, and that is ex-- I think that's extremely interesting for customers right now. I do.

DS
Daniel Simon1:06

For sure. Where have we sold deals like this before, right? Like, what are some roadblocks that I could face? Like, maybe that's not in Slack. And there, there's even, like, you're pulling stuff from the public domain too. Like, "Hey, help me do some research on this company. What are the different business units that I'm going to sell to? What are the different outcomes that these individual personas would then focus on?" And I can craft my very tailored messaging to each of those people. That's not just gonna live in Slack. So you really do need something that's much broader. And of course, there are, uh, great, like, there's legal tools out there, there's call center tools out there, and they're gonna do things that Glean cannot do. But you're always, ev-- like, the first thing that everybody does in a company, and I'm sure we've all had an experience with like Google Drive or SharePoint, like their search quality is terrible. And what a lot of the MCP-- MCP is the connectors that a lot of our competitors use, and MCP is inheriting that terrible search quality. So if you don't rebuild the context engine, you're gonna have a really tough time finding the most accurate answer.

JM
John McMahon2:06

Which again, is gonna go to how the user uses, you know, at the executive level. So talk to me a little bit about, like, I think selling in your environment is not just selling at the executive level. It's like, if I was selling your product, I would be selling to Dan almost as much as I would be selling to the CEO or CFO of a company, 'cause at the end of the day, how they are going to look at a success of any AI strategy is, if I turn it off, will Dan scream?

DS
Daniel Simon2:42

Yeah.

JM
John McMahon2:42

Will Dan have a problem? That's my, right now, that's my ultimate, [chuckles] my ultimate measure right now. If you take away any of these tools, will the rep, will the, will the user, will the end user scream?

DS
Daniel Simon2:53

For sure. And I think that goes back to multithreading, is I want multiple people to scream when that turns off. So how, I, I'll talk about a, a recent deal I sold at a really large, uh, e-commerce company. So the way I landed at the CTO, he then passed me down to a couple of different personas. There's somebody who leads the AI program for the organization. She has a

2Episode notes

Winning complex deals requires more than executive sponsorship. The strongest business cases are built by connecting value across the organization. Daniel Simon shares how he worked with stakeholders across product, engineering, finance, HR, and legal teams to uncover specific use cases, quantify time savings, and build an ROI story that resonated from end users to the executive team. The result was a business case that transformed AI from a technology investment into a measurable business outcome.

Daniel Simon is an Enterprise Account Executive at Glean, where he helps large enterprises deploy AI solutions that improve knowledge discovery, productivity, and decision-making across the organization. He brings experience selling complex technology solutions into Fortune 500 companies and navigating multi-stakeholder enterprise buying processes.

Connect with Dan:

Resources mentioned:

Listen to the full episode:

  • [Selling Enterprise AI with Context, Adoption, and Measurable ROI with Daniel

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