The TRUTH About Selling to Fortune 500 Companies

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Sidney Jones
August 2, 2022
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Selling to Fortune 500 companies can involve more steps than selling to small and medium-sized businesses (SMBs). However, when we take into account that Fortune 500 companies generate two-thirds of the U.S. GDP, the returns you can get when a major brand wants to do business with you are incomparable. If you can get a household name like Microsoft or Apple to buy your product or service, the revenue and the greater authority you can establish are well worth the effort.

The issue with selling to Fortune 500 companies is that you can’t do the same old things you would do with other prospects. Selling to Fortune 500 companies requires you to re-think the tactics, the scripts, and the pitches you normally would make in order to successfully close.

At Seamless, we’ve sold our award-winning sales software to major names like Amazon Web Services and Google, so we don’t just know what it takes to earn the business of an industry giant, but we’ve gone through strategy testing and optimizing so you don’t have to.

In this article, we will go over what to expect with Fortune 500 companies, and the secrets you can leverage to broker a lucrative deal that has the potential to expand to additional departments and other big names.

Brace For a Slower Sales Process

As the Zendesk Blog points out, the average sales cycle when selling to businesses could take several months of meetings, pitches, presentations, emailing back and forth, and persuading all stakeholders before making a sale.

With Fortune 500 companies, expect the sales cycle to be double the length of your usual process with an SMB because they typically have more decision makers, more stakeholders, and more red tape.

But don’t look at the slower sales cycle as a negative, take it as a nurturing opportunity and get hands-on with your prospect. Instead of taking a hands-off approach and leaving the organization to their own devices, walk them through their own decision making process. This way you’ll always be up to date with where the deal is in the funnel. Plus it gives you the chance to build trust with the company, which is KEY to closing the deal.

In order to better navigate the decision making process at your prospective Fortune 500 company, find out…

  • Have they used similar solutions to solve their problems and achieve their goals?
  • Why did they go with certain solutions in the past?
  • What steps did they take before they finally purchased the solution?
  • Who were the key decision makers?
  • What would key decision makers need to see from you NOW to say YES?
  • What’s the typical timeline for purchasing decisions?

Use these questions as a starting point, and gather as much intel as you can to figure out the bottlenecks in the decision making process, and the ways you can make things run more smoothly.

An added bonus to this intel gathering is you can use it to strengthen your approach to the next enterprise deal. Constant optimizing is always the name of the game.

In order to get answers to these crucial questions, you need a trusted insider at the company you’re trying to sell to. This is where the next tip comes into play…

Identify Your Insider

When you’re trying to sell to a Fortune 500 company, you always want to have a reliable contact at the organization. Someone who can answer your questions, help you figure out the decision making process, and connect you to the right people.  

In order to find that person, don’t focus on the job position because Fortune 500 companies vary greatly. In other words, the VP of marketing at one Fortune 500 company will have different responsibilities, compared to another marketing VP at another organization.

So instead of identifying an insider based on their position alone, visit the company staff page, check out LinkedIn profiles, and identify your insider based on their KPIs and their seniority at the organization.

Doing this research will not only help connect you to the right person, but you’ll be able to deliver a personalized pitch based.

Leverage LinkedIn Ads

LinkedIn ads are one of your greatest (proven) tools you can have in your arsenal to pique the curiosity of Fortune 500 companies and earn their business.

All you have to do is…

  • Figure out the target you want to go after (position, industry, etc.)
  • Strategize what you want to advertise like a demo or free trial (go with something that is zero stakes and requires you to meet one-on-one with the prospect to try to close them)
  • Create your ad using LinkedIn Ads

Once you launch your ad, optimize (copy, etc.) based on the data you receive.

Nurture, Nurture, Nurture

One of the more daunting tasks with selling to a Fortune 500 company, is figuring out what to say to them.

How exactly do you pitch a Fortune 500 company?

Every day we’re all getting SLAMMED in our inboxes and our DMs with tons of sales pitches and offers. And you can bet a well-known Fortune 500 company is getting hit with 100x the amount you’re getting.

So how exactly do you cut through this thick wall of noise that Fortune 500 companies deal with on a daily basis?

Well for one, don’t assume that your go-to, plug and play elevator pitch you use on every prospect is going to cut it here. Leave Ole Reliable on your desktop because if you try to use the same generalized pitch you always use, you’re going to sound like the thousands of salespeople who reach out to your prospective corporation, and you’ll get quickly rejected.

Instead of crafting a pitch that focuses on selling the company, distinguish yourself from the crowd by delivering value.

Think about that for a second…

Fortune 500 companies get pummeled left and right by people trying to sell them all the time. People trying to get something from them without giving anything in return.

By contrast, an email or a LinkedIn message where someone is offering samples or a white paper is like a breath of fresh air, and it increases your chances of getting their attention.

Additionally, when you’re going through the sales cycle with a Fortune 500 company, make nurturing your #1 priority.

It’s well-known that nurturing generates more sales. In fact, nurtured leads make 47% larger purchases than non-nurtured leads.

This couldn’t be more true for Fortune 500 companies. To successfully sell them, you need to nurture as much as possible. Frequently share content with them (webinars, videos, white papers, e-books, etc.). Track the content that strikes a chord and the content that falls flat, and optimize your approach to nurturing for other organizations.

Show Your Solution Is Zero Risk

Fortune 500 companies have huge revenue streams and substantial authority in their industry.

Even though they are industry giants, they are highly protective of the credibility they have earned, which means they aren’t keen on taking any kind of risks.

Should a Fortune 500 company take a risk, and not get the expected outcome or have something go awry, this could not only damage the reputation they worked so hard to build, but possibly erode their shareholder value.

It’s therefore your job to prove to the prospect that your solution is reliable and of no risk. This is where social proof like case studies, testimonials, reviews, awards, and press highlights all come into play.

In addition to showing the prospect this social proof, if it’s possible, point out to them all the different ways that your company reduces risk (solution guarantees, easy cancellation process, full refund policies, customer service for troubleshooting).

Go the extra mile and offer to personally set up your solution and make yourself available over the phone for the first month, should they have any questions.

All of this should help put the prospect’s mind at ease and increase the likelihood of saying “YES” to your product or service.


  • When you’re selling to a Fortune 500 company, don’t leverage the same strategies, processes, and scripts that you would with SMBs. Expect just about every step of the way to be different
  • Prepare yourself for a slower and a much more complicated buying process
  • Find a target insider at the organization, and gather as much intel as you can about the company’s decision making process and their past history with similar solutions
  • When you look for an insider, focus on target KPIs, job responsibilities, and seniority, not job title alone because this varies from one Fortune 500 company to the next
  • Use LinkedIn Ads to attract the attention of executive roles at Fortune 500 companies
  • Nurture the prospect as much as possible and get creative with the content you send. Make delivering value your #1 priority
  • Use social proof to put your prospect at ease and show how your solution is ZERO risk

Selling to Fortune 500 companies is complex but can extend your brand to a wider audience and help take your organization to new levels!

Leverage these secrets to elevate your prospecting game and close your next Fortune 500 deal with the greatest efficiency. Happy selling!

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