Selling to huge profitable enterprises is the holy grail of any B2B company. But how do you get the Walmarts, Apples and General Motors of the world to bet on your products or services? Take some advice from a few companies which have done it. Check out these quotes from a handful of startup executives who say selling to the Fortune 500 isn't as hard as you might think, if you handle yourself right.

1. Teach them how to navigate their own purchase system.

"When you are solving a problem in a new way, many people in the company you're trying to sell to don't know how to purchase your solution. 'Does IT pay for this?' or 'Does Marketing pay for this?' are two common questions we hear. This confusion can paralyze clients as it creates a huge barrier to overcome before they even try your product. You need to lower the barrier for getting the PO as low as possible. You could charge so little for a trial that they can put it on their corporate card. And if you have insight from prior experience, you can be their coach through the whole process, making sure that they are putting their best foot forward. This gets you the sale, and as important, makes your contact look like a hero."

--Kristi Zuhlke, founder and CEO of market research data retrieval company KnowledgeHound.

2. Know your prospect's "burning platform."

"[It's] that all-consuming issue that drives a company's business decisions. For example, we offer a virtual reality technology platform for retailers and consumer brands, whose burning platform usually includes moving faster as they compete with smaller, more nimble competitors. As such, when we talk about what we do, our focus is on how VR can speed up their store concept development, research, planning and activation processes. If the burning platform was to be innovative, we would talk about all of the creative ways our technology can eliminate bad ideas and focus on good ideas, [but] faster. Besides creating a sense of urgency, speaking to a Fortune 500 company in the context of their burning platform tells them that you know their business and are well-suited to help."

--Brooks Augustine, chief customer officer of InContext Solutions, a provider of virtual reality solutions for retail.

3. Listen instead of selling.

"We spend a lot of time making sure we find the right hiring managers to talk to, so when we do reach out we're doing so in a very natural way. And then, when we have our first meeting, we don't sell anything--we listen and learn. The insight we gain from listening--and the alignment it brings us with our prospects--is a big part of the success of our hiring-automation platform's focus on hourly workers and the on-demand workforce."

--Keith Ryu, founder of recruiting software company OnboardIQ.

4. Don't be intimidated, they're people just like you.

"No matter the size of the company you're talking to, you're ultimately connecting with a single person, who, like most people, probably likes things such as proof of success, kindness, a little sense of humor and not working with jerks. And second, from the very start focus on how you can be meaningfully helpful to a prospect. Listen to them, put yourself in their shoes, and offer them resources that will help them do their jobs better. If you are human--and again, not the self-serving-jerk kind--and show real value--not the fake kind--the sales will follow."

--Craig Root, director of enterprise sales for Jellyvision, a communication platform which helps employees make benefits decisions.

5. Don't worry about Fortune 500 companies copying your idea for themselves.

"All companies, no matter their size, have serious constraints on internal resources, in particular when it comes to technology and development. The fact is, it is often less costly for them to purchase your goods, services or in some cases, acquire your entire company, than it is to allocate a team and develop a new product from scratch. Once you have demonstrated to a Fortune 500 company that your product can be a true differentiator for them, it is essential that you convey the message that you will be giving them a valuable head start. And throw in your ability to continually innovate and pivot your development resources on a dime for good measure. No large company has claim to that benefit."

--Heidi Brown, founder and COO of Options Away, a travel technology company.

Published on: Sep 20, 2016