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As a hacker-turned-seller, it's a really eye-opening experience getting out from behind the screen and talking with enterprise customers. This post hits the nail right on the head - the sales cycles at large companies are loooong. You speak in July and it sounds like they'll buy from you tomorrow and then next you know, your follow-up emails go unanswered and you think they've lost interest, only to be surprised they want to meet in person again in September because now Person X wants in. And this goes on & on.

Two tips I've learned:

1) Don't discuss price up front if you can avoid it, especially if you're in the 6-7 figure price range. Try to get as much info as possible about their problem. Get them invested in you at a personal level.

2) If your emails go unanswered, instead of sending emails like "Hey wondering if you're still interested" send update emails about your product like "Hey Bob, just wanted to let you know we updated X so now you can do Y. Here's a video explaining more." I've had lots of success with this tactic.

As a hacker-turned-buyer, these are good tips. Especially #2.

I have a couple guys emailing me like crazy right now. I'm not responding. Why?

Nothing has changed. I don't need to respond every day to tell you nothing has changed. I start to get frustrated, and it turns me from an advocate into someone who just wants you to go away.

It's not that I mind talking about the issues, it's just.. if I say I don't have budget now, you asking me every week is not going to change that.

If instead you're telling me about what's updated, if something you've updated increases my business case, then that's actually actionable information I can do something about.

"if I say I don't have budget now, you asking me every week is not going to change that."

That's exactly the reason #2 is such a good idea (I do a version of the same in some cases).

You keep your name in front of the prospect w/o being annoying and requiring them to do anything. Along those lines though any contact if excessive can be annoying.

Thanks - a great tip from a different viewpoint.
Really interesting tip (#2).

We've just entered into the B2B world and it's been every bit the eye opening experience you've described. Neither of us counted on how long it would take to close deals. We've figured out a few of these things along the way (trying to make sure we have an advocate and a buyer) but there's a lot of other good advice in this article that we'd never considered.

It can be very hard to read what a company might be thinking/discussing internally about your product. We actually do a bit of free work up front to show people what we can do and even then it can be quite hard to get useful feedback. Oftentimes we've come to the conclusion that they're just not interested only to find that on the next phone call they're ready to start paying.

Having come from a consumer world it's quite demoralising starting off in B2B. You often feel like you're never going to get anywhere but with enough persistence we're managing to make things happen.

Comments like yours (and articles like this) are very good for lifting the spirits :)

Do not email.

Or, to put it more bluntly - fuck email.

You want the sale? Pick up the damn phone. It is sooo easy to be an asshole over email. Brush it off, never reply.

You want a follow up? Get the person on the phone. Lots of nerds hate the phone - the great sales people work it like nothing else. Always smile during the call, it shapes your voice.

Wrong. Email first and second, and only call after receiving contact back. I get so many cold calls from vendors I don't answer my phone anymore unless the number comes from one of three area codes or is someone already in my contact list. And god help you if you block caller ID.
100% about #1. I don't even mention price or anything until we're at the stage of "So, you ready to start?" I want to hear absolutely everything first. When they are ready to start, then you discuss price.

I used to start off with my rate and found that it makes customers uneasy as they try to tailor their game plan to your rate. It's a looming overhead for them.

Great blog post, lots of great information.

A few tips and tricks from my practical experience:

* Big companies still have cultures. If you understand how the culture works, it's easier to get things done. In the best enterprises, you can just straight up ask "how do things get done around here" or "What is the culture like? Who are the stakeholders on a project like this?". In fact, asking people in B2B works a lot better than B2C because often you'll get people revealing their actual painpoints

* Fear of loss is a more powerful motivator than potential gain

* Followups are everything; I can't tell you how many times I've called a company 12 or 18 months later and gotten a deal just by keeping in touch

* B2B is ridiculously personal. Be likable; send people candy on their birthdays, if they have kids send them gifts for their kids (we send/give away branded Kazoos, which also happens to be the name of our product). The sales process often comes down to (unfortunately) who the decision maker likes the most. This isn't actually a bad way of doing business (although it can be) because when the chips are down having an antagonistic vendor-client relationship is terrible.

My two cents.

Source: I'm currently managing marketing for a bootstrapped telecom company that just cleared 30 employees. We sell straight B2B and these are tactics that have worked over the last 24-36 months.

Be careful with gifts. I work for a large corp and we have to be very careful about what we accept lest it be construed as a bribe.

Birthday card is OK, accepting gifts for my kids would probably get me fired.

On another level, giving my kid a kazoo may not be a way to gain my favor.
I think a card for the kids or a quick email is more what I had in mind.

We've received a box of twizzlers in the past. We don't eat twizzlers but it was a nice sentiment.

Minus the gifts part, this is all terrific advice. As the person-in-charge-of-apps/collab at a large enterprise, I typically have 3-5 vendor meetings per week (this week I have 8... this kind of thing is probably why a lot of you hate working at/with/for large companies!), most of which I have no intention of purchasing from, but all of whom have something in their unsolicited emails that piqued my interest. A lot of times it's market research: if I'm reasonably happy with New Relic, I may still want to see what Appneta and Compuware can do for me. If I want to step up from Hangouts/Skype to something with QoS but not Telepresence grade, I probably want to learn about Fuzebox, Vidyo, Bluejeans, etc. If I'm a Google Apps customer, I am likely in touch with the kind folks behind Flashpanel, GAT, and Cloudlock. If I manage our data centers, I most likely have contacts at all the major server/storage/virtualization/infrastructure vendors. One of the most important parts of our job is to know the landscape and be able to make the best decision for our company. A lot of times we don't have the time to perform adequate due diligence, and this is where a skilled salesperson will succeed where an average salesperson will give up. You need, as josh2600 says, to make it personal, to truly understand your target, and to pitch what they want to hear.

And remember that all signed deals absolutely must be win-win. If your sales target feels or knows they're getting screwed, you're toast.

As an aside, also know that the days of "no one got fired for choosing IBM" are over. BigCos do plenty of deals with startups and small businesses. I could give examples of where that's worked out great for us, or terribly. I could also give examples of where choosing the 800lb gorilla was an awful decision.

If you don't enjoy this kind of existence, being an IT exec at a big company is probably not something you'd have fun with.

Be likable; send people candy on their birthdays

I've heard this kind of thing before, but something has always bugged me... how do you know their birthday? I have a hard time picturing a point in a business relationship where it would seem natural to ask someone when their birthday is... and if you did ask, I can't escape the feeling that it would feel "phony" or something, exactly like you were just going to use that knowledge to try to game them to buy more, by, say, sending them a birthday card.

So how do you deal with that? Do you just ask people what their birthday is, and they happily tell you, or do you at all try to "disguise" your intention by just working it into a conversation somehow, etc?

Echoing the comment below me because it's great advice.

How do you know your friends birthdays? You either ask or you look it up on Facebook. How many times have you added a client on Facebook? Seems weird right?

If you did add a client on Facebook, you'd know more about them. You might discover you both like capoeira or that you both hate Nopa, or you might discover they love cilantro and you hate it. Whatever it is you discover, it'll be 1000000x more personal than trying to sell them on your product.

So how do you get their birthday? By being their friend. Big partnerships almost always consist of big friendships.

This is really, really obvious, and MANY people don't get it.

Be genuine and build a real, no shit relationship with the person. Become 'work friends'. It'll come up - you probably know when your coworkers birthdays are, etc., right? The great part about biz is you just need to be in the right month ('hey, I heard your birthday is this month, heres X').

But really, don't be phony, and treat it like a real relationship with someone you'll be working with, and most of this stuff just happens.

The most important thing at my company is culture, glad you touched on it.
Good tips here--enterprise sales can be... interesting...

Best book I've ever read on selling big ticket items: SPIN Selling by Neil Rackham. Engineers would love it (and it's short!)

Basically, you sell million dollar computer systems with the following process:

>> (S)ituation -- what are they doing now?

>> (P)roblem -- what is the problem with that?

>> (I)mplications -- how much is that problem actually costing them? -- as a number, it's always bigger than people think, particularly if it involves people doing some manual process somewhere

>> (N)eed Payoff -- Imagine your life if you fix this problem and imagine your life if you don't. Wouldn't you much rather lead the former?

The instant rapport quick close doesn't work in these cases (in fact, it hurts you)--you need to demonstrate real value, real ROI (as mentioned in the article) and you've got to do that by taking the problem and blowing it up really big, then offering two paths and letting your prospect make the obvious choice. Or something like that :-)

That sounds useful. I'm also a huge fan of Mark Suster's PUKKCA methodology: http://www.bothsidesofthetable.com/2013/06/13/why-your-start...
As I'm getting more into sales I've just read a couple of books about the topic.

SPIN Selling is one of them but as an engineer I liked Solution Selling by Michael Bosworth even more, as it gives you a similar, but even more detailed process to follow.

http://www.amazon.com/Solution-Selling-Creating-Difficult-Ma...

I wish the startups I worked with had the SPIN you just outlined figured out.
You sound like a buyer who still has pain that is not being fulfilled :-) Why not share?
This is a great overview. I would be very interested in seeing a followup on the "air war" subject: not just PR, but social proof and validation in general. Getting a warm introduction and a set of meetings is not a trivial task, and "hacking" the organization's structure and needs even less so. But oftentimes, the final barrier to a sale -- especially for early startups -- is social proof.

In the back of his or her mind, the buyer is probably thinking things like: "Will these guys be around in 5 months?" As a small startup, the burden of proof rests entirely on your shoulders. The bigger guys have already proved themselves, and, while your service may be much better -- and while the potential customer may totally understand that -- the incumbents have incumbency going for them. That's no small advantage.

Another key thing to consider: departments (or people) within any given company tend to be profit centers, cost centers, or some hybrid of the two. They have very different goals, and hence, their people have very different motivations. Some people are empowered to take risks, and others are extremely risk averse. Pitching topline growth to a department mainly concerned with managing downside, for example, isn't going to get you very far.

To your point, it's typically more effective and realistic to pitch topline growth. But if that's going to be the case, then figuring out who at Company X is actually empowered to take chances on growth is a big priority. The number of these people in any given organization can be extremely small, even at large enterprises.

I'm not really thinking about if they will be around in 5 months... I assume they will if it's an idea I'm willing to buy. It's not even a question for me.

Incumbency is an advantage, and a weakness. Everyone hates what they have for some reason. Incumbency is rarely the issue.

The profit centers/cost centers idea is VERY true. I am empowered to take risk, and the people I have to change their systems are risk adverse. So you have an immediate issue that I have to deal with.

The best thing you can do to help me is have a business case vs. a competitor or competing idea already outlined.

Somehow startups rarely have this simple information prepared. It shouldn't be a shock to you that we're currently doing X.. instead of your Y. Why is your Y better than X in business terms?

The other thing, too, is that it's pretty common for contacts with large companies to include a software escrow clause (in relation to force majeur or other eventuality leading to the vendor becoming unable to continue servicing the customer). Whether the customer can keep the thing alive without the vendor's help is another matter entirely.
Great points on social proof and profit centers and cost centers. If you're pitching top-line growth, then often you want to start at the top (CxO level if you can).

How to run the "air war" could be a whole post. I think PR is the most important component, and you can actually get very far as a founder by just sending a journalist a friendly note and offering to talk. Quality of investors, team, and whether you have a personal connection to the company also matter a lot.

"How to run the "air war" could be a whole post."

Indeed, and while I realize it's somewhat tangential to your article, I'd love to see your in-depth take on it at some point.

I like your analysis of how pitching a solution depends on who you're talking to. If your service is a CRM system, you should probably be simultaneously be pitching it as leadgen to the sales and marketing directors and efficiency improvement to the COO and CFO. The topline vs cost-cutting pitch also depends on the product. If your service is designed to cut legal bills, like one YC company featured on here yesterday, then pitching it as driving growth would be just stupid.

I also flatly disagree with the OP, in that I think in most industries "Our solution will cut your spend on X by 10%" is a much stronger claim than "Our solution could potentially increase your revenue by 10%"; even though the latter will usually represent a higher potential ROI. Rational purchasers are more confident of the savings generated by substituting for a product/process with known costs than they are of achieving theoretical revenue gains.

It depends. If your product is obviously a revenue empowerment tool, then sure, pitch that, but that is not usually the case. Even money-making software is still effective because it automates manual processes, which is a cost savings... it just happens to be automating processes most companies don't actually perform at all.
I'm the OP -- happy to answer any questions those of you running B2B startups might have!
Question 1... how do you feel about the "valley of death" pricing-wise? As a startup targeting enterprise, one of the things I am hoping for marketing-wise is to price under the departmental budget line, so individual managers can buy for their own needs without setting off defensive alarms. And the product scales outward, so I can start with one department as evangelists, and then rake in more money and bigger contracts as the product spreads.

But when I think of, say, $5000/year revenues, if it's too high, I have to fight the corporate financial immune system. But if it's too low, I'm leaving money on the table when there's a ceiling on how many customers can ultimately be acquired.

I don't know the valley of death pricing you're talking about, but pricing isn't a part of the conversation for me until people have already bought in that they need it.

Pricing is not even on the list of concepts I have to consider to work through a process. I work for a very big company though.

The product scales outward thing is overrated. Startups have talked to me about this too, and it doesn't make as much sense as everyone seems to think.

You gain a foothold in an area in the company no one cares about, that doesn't mean anything. You are the least person to judge which parts of the company matter, so be careful about that idea.

I just had a company do this. They built a foothold in an area no one cares about. I had to tell them, it's about as meaningless as an organization if you had our janitors using their software.

If your evangelists are not connected and part of the decision making process, the information doesn't expand.

Startups definitely go either way. If you're trying to get under the departmental budget line and then up-sell, then you might be what I call a "New Enterprise" startup. If that's the case, don't worry about the initial revenue -- you'll get more.

I wrote a blog post on how to figure out whether your startup is New Enterprise or Old Enterprise: http://brandonb.cc/is-your-b2b-startup-new-enterprise-or-old...

I think once you answer that core question, the pricing and sales model fall into place more easily.

I'm interested in starting a start up that deals with SMB. I think a lot of your advice is very applicable but you would change anything for a deal size that's between $4,500 - $6,000 per year?
For SMB, you might try some of the "New Enterprise" models described at http://brandonb.cc/is-your-b2b-startup-new-enterprise-or-old.... Square is a great model to follow. For a deal size of $4.5-$6k, you can scale with inside sales and go pretty far. I'd avoid field sales entirely!
At large companies, a deal that small could be approved by tons of people. At that point, you don't even need a real decision maker.
I'm interested in becoming a consultant (but haven't taken any action yet). My first question is if your article applies to people like me. I'm not sure if you're selling a product or you're selling your skills as a service. Or, maybe it doesn't matter and your article is helpful to both groups?
Question 2 - How much resistance do you find to SaaS in the enterprise? SaaS reduces the support cost immensely, but a lot of businesses don't seem to trust SaaS.
Not seeing a link on your blog to your company. Had to go to your profile to see that. Any reason it's not on your blog?
So at what point (if ever) did you hire someone to be in charge of customer acquisition?
"Pitch the top line, not the bottom line ... Almost no products can cut costs by 5-10%".

This is a very odd statement that is in odds with how most B2B software is positioned. I would wager if you go into any company and look at the software installed, almost 95%+ will have a use case of reducing costs. Whether is automating your workforce, reducing inventory, optimizing product spend etc. Even software which touches the topline (like salesforce/CRM/SFA), at the end is about reducing the cost of sales not increasing revenue directly.

I just realized I've replied to about a half dozen replies to this post. I spend an awful lot of my work week talking with potential vendors, and have for several years. As the guy responsible for deciding whether to build or buy apps & related systems at a large enterprise, it's just part of the job.

I would be extremely happy to help any of you who would like some insight into how the purchasing process works, and to answer questions about selling to big companies. If you'd like to chat, to practice your spiel or demos, or anything else, please contact me. There's nothing I'd like more than to help develop software sales skills!! :-)

Work: elliot.tally@sanmina.com Personal: https://plus.google.com/u/0/110215565182616777712/posts

I wish Hacker News had more articles targeting Enterprise software. T

I'm involved w/ enterprise startup and I've found a lot of things like MVP, feeder landing pages, etc. just don't apply for customer acquisition. We have a lot of issues with targeting the software at the users, but needing approval from other people...

But thanks for this article.

Wow, this is an amazingly great post.
I wish Hacker News had more articles targeting Enterprise software.

I'm involved w/ enterprise startup and I've found a lot of things like MVP, feeder landing pages, etc. just don't apply for customer acquisition. We have a lot of issues with targeting the software at the users, but needing approval from other people...

But thanks for this article.

"Almost no products can cut costs by 5-10%."

Automation can cut costs by much more than that.

My intent is to show turn cut costs into opportunity costs. If I can improve the efficiency of critical lead engineers by 5%, it's not that I'm saving 5% cost... it's that their effort could be going to positive work that generates more revenue.
Great post Brandon! You should write the textbook :)