How to Break Into Fortune 500 Companies When You Don’t Know Who to Call (Ask Jeb)

2026-07-15

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If you sell into large companies, the biggest mistake you can make is prospecting the obvious title instead of the right one.In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount answers a question from Martin, who runs a high-end corporate gifting business and wants to know how to get decision makers at Fortune 500 companies to pay attention.Jeb's answer starts with a simple filter: are these gifts going to employees or to customers? That single question determines whether you start in HR or in sales and...

If you sell into large companies, the biggest mistake you can make is prospecting the obvious title instead of the right one.

In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount answers a question from Martin, who runs a high-end corporate gifting business and wants to know how to get decision makers at Fortune 500 companies to pay attention.

Jeb's answer starts with a simple filter: are these gifts going to employees or to customers? That single question determines whether you start in HR or in sales and marketing, and it changes everything about your prospecting approach. From there, Jeb walks through how to build a target list, how to use tools like ZoomInfo paired with LinkedIn to map an org chart and find real contact information, and why case studies and testimonials are the fastest way to make a new prospect feel safe saying yes.

What You'll Learn:

How to decide between targeting inside a large account
How to use tools like ZoomInfo paired with LinkedIn to build an org chart and find the right contact
Why big company buyers are motivated by avoiding risk more than by getting excited about your product
How to use existing customers as case studies and testimonials to build trust with new prospects
How many target accounts you actually need in your pipeline to make relationship-based selling pay off
What to do before you ever hire your first salesperson as a small business owner

Whether you're trying to break into your first Fortune 500 account or building out a sales team for the first time, this episode gives you a practical framework for finding the right person to sell to and proving you're safe to do business with.

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