How to sell to large customers

This can actually backfire if it's not done very carefully and tactfully. Reaching out to multiple people in the same organization can also make it appear that you are just blindly going fishing. Those people will triangulate, and they'll talk, and they'll compare notes. You'll need to make very sure that you've actually tailored your pitch and conversations to each of the people you're approaching.

If you're just sending the same, cold-intro email to different folks in the same company, they'll find that out pretty quickly, and you're dead in the water. By the same token, if you've been cultivating a relationship with Person X, and then you reach out to Person Y, Person X might feel that you've circumvented him, or gone over his head, and then you've bred some resentment with him. Instead, try this: if you've made decent headway with X, ask him if he thinks speaking to Y or Z would be a good idea. He may say yes, and actually give you the permission. He may even broker those introductions for you, provided he really believes in your pitch. Or he may point you in a more productive direction, with different people that hadn't occurred to you.

I'm not suggesting that the author is recommending a clumsy, cold approach to multiple parties. Nonetheless, I've seen it done so many times -- both on the buy side and sell side of consulting -- that I feel it bears mentioning. The general advice in the article is sound, but putting it into practice takes a fairly deft touch.

The sales teams that I've worked with for years (as opposed to the sales teams that aren't around anymore) have something in common -- they focus on building a relationship, figuring out wtf is going on, and bringing solutions to the table.

Other anti-patterns:

- Hyper-aggressive (ie Oracle): Their mission is to be a pain in the ass and sell your CEO a bill of goods. Your relationship is by definition adversarial.

- Mistargeted (ie Dropbox): Friendly people call every now and again. They never answer my question ("Is Dropbox on a state procurement contract?"), and don't understand why the answer they don't know is important to me.

- Wheeler-dealers: I ask for a product demo, we get it, followed by a cold quote for $3M for an off the shelf product. I don't respond, and get an unsolicited quote that is now $2M. I usually reply with an email that says "Not gonna happen."

This is talking from the direction of actively engaging a large business and selling to them. I work on the side of large business actively choosing which startups we want to work with.

"Lesson 1: In larger organizations there are multiple individuals with separate motivations involved in the buying process "

Without question this is important. I am sort of a gatekeeper in the process. It's my job to validate the companies that are seen by the real decision makers (not me). I am the technical grunt in front of the process allowing the C level decision makers to only make good decisions no matter what they decide to do.

With me, you can discuss tech on a geek level, and I'm most comfortable and at home.

To my C levels, you better be high level and respectful. We've lost the ability to work with several startups simply because they weren't able to discuss on a C level.

If you are a founder and can't discuss on a C level, hire someone who can. You could lose a tremendous level of money and momentum simply because you have no idea how to talk to someone who leads a large business.

If you are targeting SMBs, you can get away with direct sales, etc. But once you get into the "bigger fish", the sales cycle lengthens incredibly, as do the requirements from the buyers.

One of my previous employers made the transition from selling from SMBs to enterprise, and it was a difficult transition. Our product was usually bought by a department head that required it, and it would spread across the organization organically. However, once we entered enterprise companies, instead of talking to the department heads, we needed to talk directly to the CIO/CTO, who would make the decision on behalf of the entire company. This required a lot more patience, and a completely different skillset from our salespeople.

So in the case of the OP, trying to land a big fish by talking with contacts like this is likely a huge timesink, because experienced salespeople will eat guys like him for breakfast. If you're going to target bigger fish rather than smaller shops, it's best to get someone who knows exactly what the process is and is actually focused on sales. The charm of working with a startup is lost on bigger customers, who have bonuses based on uptime, SLAs, etc.

In both cases, we were providing services to a single product group within a company large enough that those product groups can act nearly autonomously. And in both cases, the corporate office came to the (quite rational) decision that having ten product groups using ten different agencies was inefficient. In one case, corp's pet agency became the agency of record; in the other case, they actually built an in-house department from scratch and stopped using agencies altogether.

If there's a moral to this story, it's to scale that ladder. If your product/service/whatever only has one customer within a large organization, your use is vulnerable to consolidation moves. But, if your one user is happy and satisfied, you can often use that to gain wider traction within a company. In addition to more customers, it's a much safer position to be in when someone from on high wants to start standardizing across the organization.

I don't know how a smaller company would be able to do this.

Who is involved in the decision? What are their primary pain points? What are some reasons they may not buy? (Paradoxically, asking for objections instead of waiting for them to pop up makes you seem more trustworthy)

Etc.

For anyone to think that Filepicker.io is not a side project, do not use the stock themed Bootstrap.

Right now, it looks straight out of RailsRumble.