How do you win Fortune 500 customers as an early stage start up?  What's the best way to approach them?

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VP of Sales in Softwarea year ago

That depends on the product or service that you're selling.
The top-down approach is hard so your best bet is to work your way from the bottom-up leverage partners, resellers, and distributors that are already working with these companies.

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Enterprise SaaS Deal Coach in Softwarea year ago

Enterprise Customers are maxed out on products and haven’t gone out of business without your solution, albeit less efficiently, cost-effectively or securely.

New technology investments require:

- Trustworthy, credible technical advocate and executive sponsors.

- A clearly defined business case which speaks the language of the C Suite and highlights innovation to disrupt the status quo to avoid ‘no decision’ losses. Emphasize business outcomes.

- Comprehensive project plan including actions, owners and dates. Highlight risks and plans to motivate them.

- Alignment of internal and external stakeholders, including SecOps, Infra, Legal, procurement and funding sources.

- A plan to land and expand based on iterative success.

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Head of Sales in Softwarea year ago

The reality is that you do it in whatever way you can. Don't overanalyze it too much, but be organized and do high quality outreach. 

You will often need to employ both bottom-up and top-down approaches.

Bottom up - find one of the persona's you'd like to talk to and who your software/service would benefit and try to book with them, then move to their team if the call goes well, then move upstream and build consensus as you go. Eventually you find your way to leadership, budget and power.

This is one way. Top down is just the opposite although the steps vary a bit but you get the point. These F500 companies all operate a bit differently but the best way to get in is to start trying and find out how to best do it based on  your product or service. You will learn quickly the best path once you start. 

Another thing, don't be intimidated to do go after the biggest companies in the world. After all, people are people. It just takes longer with the big ones. :)

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