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THE EXPLAINER
Irregular insights for people who buy, sell, use or otherwise care about enterprise software.


Tactics for Hard Times in Enterprise Software Sales
Enterprise software pipelines in 2026 are challenging, particularly for middle-market vendors. What can be done to convert leads into opportunities?
Charles Rathmann
Mar 105 min read


Why Nobody Gives a Crap About Your Software Marketing Content
One thing lost in the decline of trade publications is objectivity. An individual advertiser has a goal that may prevent them from sharing certain insights or addressing certain topics in top-of-funnel communications used to drive awareness and leads.
Charles Rathmann
Sep 19, 20253 min read


Radical Thoughts on LLMs for Marketing and Communication
An LLM may emulate human speech, but it is still a machine. Our corporeal bodies may be machines--poorly-designed, prone to systemic, acute and chronic issues and decay but machines nonetheless.
But we are not. References to Rene Descartes, Gilbert Ryle, Martin Buber and others.
Charles Rathmann
Jun 24, 20255 min read


The Way of The Stoic Marketer in Enterprise Software
Stoicism puts virtue above all other things which is hard when marketing software against those with other ideals.
Charles Rathmann
Aug 2, 20247 min read
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