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What Your Legal Technology Can't Fix: Five Questions to Ask Before You Buy
Published 10-08-2026
Legal functions often operate on institutional knowledge that has never been formally documented. As teams expand, key employees depart, or software enters the workflow, this reliance on individual expertise exposes structural weaknesses. This article examines why digitization frequently fails at the process level, long before procurement, and outlines five questions that help organizations identify whether their operations are sufficiently defined to support automation.
Does Valuation Matter When You’re Buying Legal Tech? Less Than You’d Think.
Published 10-08-2026
I keep hearing a version of the same line from CIOs, innovation leads, and GCs sizing up a legal tech vendor: “Andreessen Horowitz is investing in them, they’re smart, so the product must be good.” Financial stability absolutely belongs in a vendor risk management program. But using VC backing as a proxy for that stability is a category error.
Most Investments Don’t Succeed
Venture Capital firms (VC) investors are generally sophisticated and well-resourced. But what they’re optimizing for is a high risk, high reward outcome that isn’t a useful signal for buyers of any technology. VCs are not trying to “pick the winners” in the same way law firms are.
Instead, their approach is to spread investment across many high-potential companies, know that many will fail, and count on a small number returning 100x their investment or more to carry the entire fund. Research on outcomes puts the failure rate for venture-backed startups at around 60%. That is far beyond the risk tolerance of most law firm and corporate legal teams who are seeking stability and longevity from all their vendors.
This article explains what a valuation really tells you, what critical information about private companies stays hidden, how to navigate those gaps, and the new reality for legal buyers.
RelFest Chicago 2026: Legal Data Intelligence, From the Inside Out
Published 10-07-2026
Relativity's user conference arrived with its biggest news already announced and a main stage devoted to product. For legal departments, the more useful conversations happened in the sessions: getting to the facts earlier, making too many tools work together, and governing the evidence their own AI use now creates.
Out of the Business of Misery: 8am Kaleidoscope 2026
Published 10-03-2026
8am's own research says admin work is making small firms miserable. At Kaleidoscope 2026, the company answered with a Claude connector, new AI and financial tools, and two days of sessions on spending less, collecting more, and bringing in more clients.
Inside LTH Horizons New York: Value, Judgment, and the Rules for the Sequel
Published 10-02-2026
What do horror movies, vibe coding, and Leonardo da Vinci have in common? At LTH Horizons New York, they all had something to teach legal about AI strategy. Here's what 150-plus attendees took away: who really benefits when AI makes legal work faster, where firms are actually spending their AI effort, what it takes to build agents that deliver real value and more.
LTH GenAI Legal Tech Map: September 2026
Published 10-01-2026
As of the end of September 2026, there were 1,416 solutions in the LTH Directory that incorporated generative AI from 1,117 providers across 19 different categories. We have created an interactive map of these solutions and the categories they operate in for your exploration.
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