Alex Payne is a writer based in Portland, Oregon.

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How Not To Sell Software in 2012

Though most of our stack at Simple is based on open source software, we occasionally try commercial software. Mostly, we don’t end up buying it. A big reason why is the incredibly time-consuming, aggravating sales process that most commercial enterprise (that is, non-consumer) software vendors insist on. I’m between vendor calls today and channeling my irritation into this post.

It’s 2012. Practically everyone who’s paying for software is doing so through an app store: one click or tap and you’ve got what you want. Heck, even free/open software people have an app store these days.

Similarly, more and more people who are paying for remote computing resources, whether servers or software, do so through instantly available, transparently priced cloud services. I can give Amazon my credit card number and have everything I need to run a growing business without ever talking to a salesperson. I like it that way.

Today’s startups are tomorrow’s enterprises. Many of the other startup folks I know share the same expectations about how software should be sold. Basically, if a given software package or service isn’t free/open, it should be as easy as humanly possible to try it, pay for it, and start using it in production. If it isn’t easy to get started with your product, I’m going to find another vendor.

The List of Don’ts

If you’re in the enterprise software business, you’re going to be dealing with more and more potential customers like me as the demographics of our industry shift. So, if you’d like to keep making money, here’s what not to do:

  1. Don’t require that I waste my time on a sales call – or, worse, in a “webinar” – before I can give you my money. Instead, provide all the information I need about your product on your website.
  2. Don’t make it hard for me to try your software. If I can’t play with a trial version or sandbox immediately, I’m moving on.
  3. Don’t hide your pricing behind a sales process, and don’t play pricing games. I can find and talk to your other customers basically instantly in order to determine what they paid for your product and if they’re getting the value they expected from it. I will do this. So just put the price of what you’re selling on your site and skip the games.
  4. Don’t make me read a whitepaper in order to get essential information about your product. Put it on your website. In HTML. Not in a PDF, not in Flash, not in Silverlight or ActiveX or whatever. What your product does, on your website, in HTML.
  5. Don’t automatically sign me up for a newsletter about your company or product when I give you my contact information. Ideally, don’t request my contact information at all until I’m giving you money.
  6. Don’t make it hard for me to talk to a technical person at your company about the nitty gritty details of how your product works. If you don’t provide a forum for those discussions, someone else will, and you won’t control it.
  7. Don’t make it hard for me to pay for your product. I have a credit card. I also have a PayPal account, a Google payments account, and an Amazon payments account. Any of those are fine (although PayPal is not ideal). Any other billing process is not.
  8. This should go without saying, but don’t cold call or spam me. If your product is good and meets my needs, I promise that I’ll find out about it.

Basically, the farther away you get from being like an app store or Amazon Web Services, the less likely it is that you’re going to get my money.

Examples, Good and Bad

I’m sure some vendors think that they’re special and unique snowflakes whose products couldn’t possibly be sold without high-touch interactions with potential customers. Yet, somehow, a new generation of companies is managing to meet the above requirements, and I sincerely hope they eat everyone else’s breakfast, lunch, and dinner.

Beyond aforementioned Amazon, here are some companies doing it right:

  • Urban Airship – transparent pricing, get started immediately.
  • The Resumator – ditto.
  • PagerDuty – ditto.
  • Expensify – ditto.
  • Duo Security – ditto.
  • Skype – their Manager product for business is actually really handy, and the information on their site about it is clear and to-the-point.
  • Google Apps – their dashboard is a mess and their customer service is abominable, but pricing is straightforward and you can get started immediately.
  • Datameer – not perfect, still a lot of whitepapers and salesy garbage on their site, but I was able to get up and running with a trial version in minutes.

And, some companies doing it wrong:

  • Five9 – your site says “cloud”, but your sales process says “1970s mainframe”. Every possible sin: forced sales call, forced webinar, getting set up with a demo requires yet another phone call, pricing is hidden. Just awful.
  • GitHub Enterprise – it looks like their sales process has improved somewhat from when the product was called GitHub:FI and it took them days and days to take our money. That said, “trial licenses are subject to approval” in the current iteration, which is kinda weak. I really love GitHub and I hate to talk mess about them, but I’m only mad because I care.
  • Yodlee – pricing games galore.
  • Karmasphere – I don’t want to “request a trial”, I just want to try it.
  • Metamarkets – lots of good product information on their site, but everything else is hidden behind a contact form. I filled that form out and never heard anything back, not even an automated reply. (Updated: they got back to me and set me up withe a demo; apparently they had a bug in their marketing site come up while migrating from one domain to another.)
  • Basically everyone else in the business intelligence market.
  • Basically everyone else in the VOIP/virtual callcenter market.


I want to give you my money. Your sales process may be a bigger barrier to you getting my money than your competitors. Please join us in the year 2012, where software is available instantly and transparently priced and the word “webinar” is only used ironically.

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