While both articles address a company's outward image, I'd say that the two touch upon very different things. I understood OP's post to be more about the quality of marketing collateral and making sure that the client experience was well fleshed-out, and I read your link to be a lesson in messaging. I didn't find the two to be mutually exclusive.

I think that both articles are saying the same thing, fundamentally:

Your brand should be something your customers expect, but only just.

Smart Bear was a small, upstart company, selling cutting-edge tools for developers into a relatively new market.

Developers and their managers value directness, especially at small companies. A vendor that shows all the signs of being a peacock while obviously being a pigeon will come across as scummy, because your market is expecting one of "small upstart dude in shed" or "massive enterprise company with a headcount greater than many cities", and not something in the middle.

Iron Port's customers, on the other hand, are buying security products, and frankly, the security industry is almost all theatre. An impressive-looking website, bespoke-looking product, and glossy sales brochure is all in the ante of playing at the security-vendor table, especially before Web 2.0.

Your company has to dress for the occasion.

It looks to me like these two posts are perfectly complementary. One is right if you can only sell to big customers - and if you sell a $50,000 email appliance, you're not going to sell it to small businesses or individuals.

The other one is about selling to small businesses (and the same could be true for consumers). It only makes sense that you should use two completely different approaches.

One important corollary of the first article is, imho, that you should never start a business geared towards the big guys if don't have enough investor money, even if your technology isn't so expensive to develop. You will be very difficult to be taken seriously otherwise. And this resonates with my personal experience with multinational customers at my day job.

It's not just about the size of the sale. It is also about what you are selling and how critical that is to the company's day-to-day operations. If your code review tool goes down for a few hours, meh. If your email goes down for a few hours, the world is on fire and somebody is losing their job.

In the later case, companies want to feel that the "if" scenario will never happen. It's not that outages can't happen, but, rather, that if an outage occurs, you will be taken care of. If UserVoice is your only support tool, you are unlikely to give that feeling.

The thing that bothers me about that post is that Jason's company did OK back then. Smart Bear Software didn't crash and burn. Instead, it sold stuff and made money.

Of course, the post doesn't go into details about the company's early days. But still, saying "here's what I should have done" sounds like pure speculation.