You lost me here:<p><i>you can consider the typical “coin operated” sales person at a mature company to be more akin to a script kiddie than a hacker.</i><p>The terminology you use belies a lack of understanding of sales' place in an org and is frankly just insulting. To borrow from Lars Dalgaard [1]:<p><i>The “coin operated idiots” mindset toward sales is a mistake for a number of reasons. For one thing, it’s a kind of bigotry, because it basically writes off an entire workforce of human beings who create so much value everyday. An outstanding and involved sales force can often make or break a company. It’s why companies with an inferior product but a superior sales force sometimes still win.<p>But the real problem with the coin-operated idiots mindset is that it relegates salespeople only to the field or to the phone, when they really should be considered part of the company leadership. Not this decapitated thing you “slot onto” your organization when you need to...<p>Having a salesperson in the room means bringing in a bullshit meter. The sales rep is the one who is going to say, “I know you’re excited that this product was built on/with such-and-such, but so what? That’s not going to excite my customers. How is this differentiated from everything else out there?” They’ll ask the hard questions.</i><p>[1] <a href="http://a16z.com/2015/06/01/clean-up-your-startups-b-s-bring-sales-into-the-leadership-team/" rel="nofollow">http://a16z.com/2015/06/01/clean-up-your-startups-b-s-bring-...</a>
If any of you are a hacker trying to learn enterprise sales, a few years ago I wrote a few lessons learned at my first startup here:<p><a href="http://brandonb.cc/enterprise-sales-tips-for-hackers" rel="nofollow">http://brandonb.cc/enterprise-sales-tips-for-hackers</a><p>Mostly orthogonal to the OP, but there are a few overlapping points.
A book that helped me get into enterprise selling is SPIN selling by Neil Rackham. <a href="http://www.amazon.com/SPIN-Selling-Neil-Rackham/dp/1565114205" rel="nofollow">http://www.amazon.com/SPIN-Selling-Neil-Rackham/dp/156511420...</a><p>Based on research into the field of sales.<p>In summary one of the key differences for enterprise sales is that it's a long process with many people involved.
Great article, Ryan. You characterize large enterprise sales as being on the order of "$1M+ deals"[1]. This seems a bit high for a startup with a newish product, but it's certainly achievable.<p>Do you have any insights into how startups can achieve $1M+ in annual contract value (ACV)? What differentiates their product and pricing strategy from a startup that sells software for say $100K a year?<p>[1]: <a href="http://themacro.com/articles/2016/05/enterprise-sales-for-hackers/#e3" rel="nofollow">http://themacro.com/articles/2016/05/enterprise-sales-for-ha...</a>
<i>> Usually the more complex the system, the more satisfaction the hacker feels when he or she pwns it.</i><p>Equating "selling" to "pwning" is not a good way to think about any kind of sales. Talking about "hacking" a customer suggests that they are somehow inferior and that the goal is to somehow beat or triumph over them, to trick them or exploit a vulnerability. No company should think of their potential customers in that way.
One more important thing you need to know about the enterprise you're selling into: what spending approval levels does the champion and his/her management chain have? Often they'll have discretion over anything under 10K, and will have to seek higher approval for larger sums. This is one of the factors that has driven SaaS monthly charges as opposed to traditional perpetual licenses with six or seven figure tags.
Pretty good write up. The author glosses over the finance part at their own peril. I'm noticing enterprises with longer and longer payment terms.. As in they mandate their vendors provide net-90, which seems insane to me. It used to be net-60, and even that seemed odd. So be prepared to be flexible to close that sale.
The point about finance is interesting and probably the one I thought about the least. I think I'll think about it like NFL contracts in the future (front or back loading contracts might be good for their "salary cap" aka budget).
Brilliant article. Agree to every bit. This is kind of enterprise sales 101 of point solutions. However if you talk about infratstructure solutions (say mBaaS, etc) - things Become far more complex as many a times you may not have any business end point as your champion.