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I used to think sales hated legal. Turns out they just hated waiting three weeks for someone to approve a contract that should have taken two days. The frustration was real and it was specific. A sales rep would send over a new vendor agreement or a customer MSA, and it would disappear into a… (Read more →)
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Last fall I decided to test something I’d been hearing about at every legal ops conference for two years: AI-powered metadata extraction. The pitch is simple. You upload your contracts, the AI reads them, and it spits out structured data: party names, effective dates, expiration dates, renewal terms, governing law, payment terms, the whole catalog.… (Read more →)
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They were scattered across three departments, and not one of them matched the template I’d spent two weeks building with outside counsel. Sales had a version where someone had deleted the non-solicitation clause because a prospect pushed back on it once and the rep figured, why not just take it out? HR had a version… (Read more →)
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Last year, our CFO needed the original MSA for a vendor we were about to renegotiate. Not the SOW. Not the last amendment. The original agreement, signed four years ago by someone who no longer worked at the company. I knew it existed. I’d seen it referenced in an email. But I couldn’t find it.… (Read more →)
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I started doing this by accident. About six years ago, I walked into a Monday morning meeting and a VP asked me when the Aramark contract was up for renewal. I had no idea. I’d been managing the contracts for that org for over a year, and I couldn’t answer a basic question about one… (Read more →)
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I can tell you the exact moment I realized how broken post-signature contract management is at most companies. I’d been at a mid-size manufacturing firm for about three months. Long enough to know where the contracts lived (mostly), who the key vendors were (roughly), and which ones had renewals coming up (barely). A project manager… (Read more →)
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I’ve implemented contract management software five times across my career. One of those implementations took a single day. Another took the better part of six months and still wasn’t fully adopted a year later. The difference wasn’t the software. Not really. It was what we were trying to do with it. The day-long implementation was… (Read more →)
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I’ve onboarded maybe a dozen people into contracts or legal ops roles over the years. Different companies, different industries, different levels of experience. And every single time, on day one or close to it, I say the same thing: “Before you read any SOW, read the MSA.” Most of them look at me like I’ve… (Read more →)
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I’ve set up contract repositories at four different organizations. Three of them failed. Not because the software was bad (it wasn’t, mostly) but because nobody thought about what a repository actually needs to do before they bought something and started dumping files into it. The fourth one worked. It’s the one I still use. And… (Read more →)
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The first renewal negotiation I ever handled, I lost before the conversation started. I just didn’t know it yet. It was a document management platform. Annual contract, about $38,000. The vendor’s account rep emailed me six weeks before the renewal date with a “quick update” that included a 12% price increase and a note that… (Read more →)










