Why Selling AI Automation to Hedge Funds Is Hard
This post may save you a ton of grief.
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One of the most difficult markets to sell AI to is the hedge fund segment—and to a lesser extent, PE, VC, and sell-side trading desks.
In this post, I’ll go into some common challenges selling technology to investment managers (from boutique shops to megafirms), what makes them hard to sell to, and what you should be offering—if you’re set on selling AI into this world.
And by AI, I mean the typical B2B AI software stack in 2025: “enterprise AI platforms,” “document automation,” “AI employees,” “intelligent knowledge management,” etc.
These thoughts are based on:
conversations with industry professionals about the state of AI in front-office finance as of mid-2025
observing other founders who struggled to sell into this segment and eventually pivoted
my personal experience as a trader building internal automations pre-2014, and some more recent automation work in finserv.
Of course, they’re just observations. YMMV.
You can probably still close a deal if you have strong top-down sponsorship. But as of 2025—nearly three years after ChatGPT’s launch—there’s still a remarkable lack of real success stories… aside from ChatGPT.
Let’s get into it.
