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It does bug me when I'm expected (and in some cases, nearly forced) to use licensed software for work that they won't buy licenses for.
I'll spare you the need to click through to this article. Basically, there are enterprise users and enterprise purchase decision makers. The article says you can't fail to market your product to the latter in addition to the former. There are no recommendations as to how to do so.
(Author)

My struggle with writing is I start out wanting to share an idea, but then I get caught up in the details and before long I'm writing and editing--or, realistically, procrastinating--a 2,000-word article that overshadows the main point.

Lately I've challenged myself to say just enough to express the idea, and nothing else. Maybe I'll write about the execution details later, but for now I just hope to get people thinking.

I can agree with your point and share the struggle however this article was quite too shallow
Noted. More to come!
Great!

I am struggling as well with a similar problems and the more I am educated about it the better!

Perhaps a series approach might help? You've set out this generalized article, it gets the point across. Now, you could take each major piece and roll a specifics and execution article (hurray for more procrastination!).

[edit] This would allow you to say just enough to get the point across, while still doing a deep enough dive on points that need more tactical information. [/edit]

Agreed. More to come soon.
Thanks for the article, but I agree with the parent of your comment. I'm struggling with the exact problem you describe right now so I was eager to click on this article but came away without much new info. I know this is my problem, but the execution details are what I'm lacking! Cheers.
Tip: Write everything down, fast, leave notes where you get stuck. Then relentlessly remove things that are unnecessary, and finish the parts you just left as a note. You can also move less important stuff to the bottom, as very few people read all the way to the bottom anyway, unless they are really interested. I also like to have an TLDR/abstract at the top.
I like this advice, it resonates with my lived experience. I've thought about this some, and the organizational design of enterprise companies is often so different from the leaner designs of startups that the dynamic of needing to have language for buyers can be a org blind spot. On the buying side, I've experienced frustration more than once because it wasn't obvious how I connected the people who could buy me tools with the company who wanted to sell it.
Enterprise has been a constant frustration for me. I never really wanted to sell my software to big customers but you can't put a sign out front saying go away if you are big and bureaucratic.

Over the years I've had a regular stream of people who want me to agree to 30 pages of conditions or offer credit terms for a $99 sale. The reality is you can't afford to engage with Big Co's purchasing department with sub $10K price points.

I can imagine going through the IT department will be a problem but I can for example buy pretty much anything with 3 digit price without much fuss. Not sure how other companies handle it.
That's done on purpose and for good reasons. Big Co's want to deal with Big Co's because they move at the same (low) speed, have a long lifetime, big projects, and are not afraid of complex negotiations and lawyers.
Enterprise or no, I see a lot of developers (and entrepreneurs) take the approach of "If you build it, they will come".

That is just not true in most cases.

We all know these products with elaborate dashboards, too much reporting, too many data points. Those are created simply to appeal for the decision makers.

You sell to developers by a better UX/UI and workflow, you sell to decision makers by telling them how they will get a better view of things and manage teams better.

You have to build both ends, and you have to sell the decision making end much better and much more aggressively.

Edit: typos

You also have to know your audience.

storytime:

We had a demo scheduled with a company. We were shopping for a security auditing system for dependencies across all GitHub repositories.

The person going through the demo did an absolutely terrible job at reading the room and understanding who they sell to (right now). Focused a lot on reporting, compliance while we cared more about the mechanics.

Kevin from http://fossa.io here. Did this happen to be us?

If so, I’d love to hear you feedback on our demo, if not I’d love to offer you a demo.

kevin@fossa.io

funny how Kevin's nick is XiZhao
Not really that funny -- a lot of people with Chinese (I think?) names also adopt an American name to make it easier for people to spell, pronounce, etc.
Yeah, my name is Kevin (Xi Zhao) Wang.

But the funny thing is that a slightly different pronunciation of "Xi Zhao" changes the meaning from (roughly) "western prosperity" to "morning bath".

Can confirm. I have basic Mandarin and I would have definitely thought of you as the guy named "take a shower" if you never explained.
I've been a member of a very traditional Chinese martial arts club for years. I've only ever known most people by their Chinese name and been surprised at times when I catch them being referred to by a Western name. Others use either inconsistently or are mostly known by the Western name, so it happens here in Australia too.
Sales pro tip: The first thing out of your mouth when trying to sell someone is to ask who they are and what they need. Once you have established those two things, you then tailor your pitch to match exactly that and no more. For example, if you're selling a Thingmabob and your target is a small dentist office in the mid-west concerned about filling their schedule, then spend the time telling them about how other dentists' offices have used your product to attract new customers. Don't spend any time telling them about how Thingmabob helps to drive down costs even though it does this 3x better than the competition. Sell people what they are buying not what you are selling!
You can present to people, or be present to people. Sales would be much better if it was much more of the latter.
Exactly, one of these two things is more likely to get you in the door, look splashy on demos, and convert an evaluation into a PO.

The other might help get you a renewal after the initial contract is up, but on the other hand, once something is in the budget and established, it has to be really, really awful to get kicked out and go through the process of finding a replacement. Voila, enterprise software!

I feel you can also sell from the bottom.

Slack, for example, a lot of the requests came from engineers to work with it.

The product has to be REALLY good though, for most, this is a very hard sell

Ehh, most of the engineers at our org would have been happy to stick with Hangouts and just commenting on PRs and JIRA tickets. Slack adoption ended up being driven from non-engineering groups like marketing and sales, and then eventually mandated from the executive level.
Too many conversations are held in Slack and not in the tickets, now.
It's a weird thing, because JIRA can end up having so many fields and so much enforced process that it feels like there's a lot of overhead associated with creating and closing tickets, and you always know that those actions are potentially feeding into and messing up someone's reporting somewhere.

So you end up talking on Slack about an issue someone's noticed, and then trying to decide whether it's "worth" the bother of creating a ticket for, or if someone's aware of a ticket already for it, or or or.

My company pays for MixMax, Zapier, Slack, Mailchimp, AWS, RingCentral, Gsuite, and more. Our purchase decision-maker (me) evaluates and buys the product, while our users are along for the ride, reserving their judgment until the merits of the software are felt. As I continue to evaluate new software, and as I watch our SAAS overhead rise, I am looking for software to cut. I'm not a Salesforce shop, but expect this is a serious issue for those purchase decision-makers... paying for many SAAS add-ons in addition to the platform itself.

So, I would advise SAAS providers to keep a close an eye on their existing users. We are looking to control our expenses and will leave for higher impact, lower priced alternatives. I recognize this is tough to do when growth and other acquisition/IPO metrics are pressed by your investors.

My overwhelming sense: if you're not marketing, enhancing and listening to your existing users, your falloff risk is mounting. Surveys and polls aren't enough. Pay attention to your superusers. Add a client or two to your board.

Keep new users close, but your existing users closer.

I find "What is the value we are getting?" to be the absolute most crucial question.

We were paying a few K$ a month for DataDog. The value we were getting from it was quantified. We evaluated how long it will take to build the features we are using from DD ourselves. It took about a month and we cut them off completely from our stack.

If you take the AWS approach, you have to keep providing value and you have to keep getting your users to buy-in.

I don't know if there's a very good way to actually communicate with all of your users, emails you get seem to mechanical and artificial. "What can we do better?" type of emails don't really work.

On your "manage the saas", did you see https://toriihq.com/ ?

One thing that I find to be ridiculous with companies (especially at an early stage) is that they have tactics but no strategy.

They try something for a week, it doesn't work, and they move on.

OP here, for example, has an article about selling through Quora. It might not be up your alley, that's fine; If you decide to do it in your company, have someone actively work on it on a weekly basis, develop a strategy for the point you are trying to get across and nail down the message. Don't answer a single question and look at your Google analytics trying to see how much traffic you got from it. Do it consistently until you either figure out it works (or not, of course).

If you decide to sell to decision makes, this should be your strategy, you can't decide today you are selling to X and tomorrow you are selling to Y.

When you make a decision like this, inform the product managers, they now need to build different things. Be honest and be vigilant about it.

We have a big problem with these in my org. High execs buy software that sucks (From HP, Microfocus, CA, Oracle). They literally have to force people to use it. A lot of money is thrown so people use it. Even after everybody realizes it is bad software. Because somebody high up has to save face.

Meanwhile other software just is being organically, underground until everybody uses it and it cannot hidden anymore. As an example, Git took years and years to be accepted. Now everybody wants to get on board.

The bigger cost is not to buy shitty software. The bigger cost is failing to acknowledge it and move on.

I’ve always thought software should try and delight the user. The first software that made me feel that way and rush to happily pay for it was Beyond Compare by Scooter Software. I have been 100% pleased with it. Other software I was happy to pay for includes Sublime Text, TextPad and even Windows 7 Professional.
I very specifically stopped targeting “buyers” in favor of individuals. The buyers want us to develop “whips & dashboards”

Lucrative! Not what we want to build.

That’s one of my favorite aspects of being self-funded and profitable.