How to sell to large customers

<i>"The competitor had done all this work by going around the organization, interviewing the stakeholders, putting together presentations and data dockets that addressed their needs. This was work that Richard would have had to do otherwise. Thus, the competitor had helped Richard help him!"</i><p>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.<p>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.<p>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.

I guess that works for this guy, but as someone in a big enterprise, I'd be really annoyed with a vendor that is venue shopping. An an outsider, you have no idea what the internal politics of the organization are. Getting blindsided because some salesman took my colleague to lunch is a great way to get a project derailed. (The conversation can shift to "how do we implement product x" instead of "how do we solve problem y")<p>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.<p>Other anti-patterns:<p>- 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.<p>- 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.<p>- 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 part of my job, buying from the side of large companies so I will provide some input.<p>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.<p>"Lesson 1: In larger organizations there are multiple individuals with separate motivations involved in the buying process "<p>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.<p>With me, you can discuss tech on a geek level, and I'm most comfortable and at home.<p>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.<p>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.

This is why you need a dedicated and experienced sales person. Selling to a small company is one thing, but selling to a larger customer is an entirely different skill set. And then selling to enterprise is even more different. The sales cycles differ tremendously depending on how large the organization is.<p>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.<p>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.<p>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.

The first point hits close to home; I have twice been in the position of losing happy, paying customers due to other decision-makers getting involved. I work for an agency, not a start-up, but it's the same process: convince someone within an organization to pay you large sums of cash for services.<p>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.<p>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.

Great post! An oft heard question, we get as a start-up selling to large enterprises is - How will you meet our need for these N custom features? Being constrained on the software development side, we've found it helpful to triage the client needs and lay out a phased plan for development. Also finding a champion for our product in the client organization, usually a mid-senior level executive, who can coach us through their decision making process has been helpful

There is an interesting tidbit in the article about the other vendor doing a proof of concept. I work for a large enterprise and I’m working with a company that has gone to great lengths to facilitate a proof of concept. We're using ~$250K worth of their equipment and weeks of their time, not to mention travel and all the expenses that entails. As far I know, we haven't given them a dime yet.<p>I don't know how a smaller company would be able to do this.

For complex sales, one thing I've found that really helps is to create a worksheet and use it during the sales call. It asks things like:<p>Who is involved in the decision? What are their primary pain points? What are some reasons they may <i>not</i> buy? (Paradoxically, asking for objections instead of waiting for them to pop up makes you seem more trustworthy)<p>Etc.

Nice summary. That's what makes enterprise sales challenging and time consuming and why Steve Blank spends a lot of time in his book explaining how to navigate it. What are some other common objections/challenges you've run into and how have you overcome them?

I'm always partial to any post in which a start up actually admits that a bigger competitor did something better, even if it's lowly sales.

You <i>partner</i> with large customers.

Also as a side note:<p>For anyone to think that Filepicker.io is not a side project, do not use the stock themed Bootstrap.<p>Right now, it looks straight out of RailsRumble.