I'm more interested in ingenious and creative means like growth hacks that may have worked for you. But general methods are welcome as well.
You can create a free limited functionality version on the WordPress repository. Then inside that app try to upsell to premium version.
OoOh. Growth hack!
Every event needs a page. Create targeted landing pages with a particular goal in mind for each, education, download, share, feedback, etc. then promote through the various Wordpress 'local' groups in Facebook for various cities (markets)
Create a website for FAQ and promote that as well.
Go to Quora and ask for feedback there.
Go to ProductHunt.com and ask for invite and article to be posted there. Start by asking for a review from someone there - find them through Twitter and let them know is for Quora.
Schedule a Meerkat event and stream it on Twitter with relevant hashtags. Offer a discount there. The RT love can be huge there .
Hope it helps!
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Best of luck!!
One of the most sucessful models for premium plugins is to offer a core plugin for free then allow installing add-ons. These premium add-ons could be created by you or the community. For successful examples, see Easy Digital Downloads, Ninja Forms and Woocommerce.
I have been selling WordPress plugins for 3 years and currently own and operate a small WordPress plugin marketplace.
Hands down the best way to reach new customers is via a free version of WordPress.org. That said you do need to be careful not to give too much away for free. If you need some specific advice on that let me know.
Also it is definitely useful to be a part of a marketplace. Choose wisely! If you need some advice about that let me know as well. :) Setting everything up correctly is essential in maximizing your sales.