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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 →)
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I almost cost my company $87,000 once because I missed a renewal by four days. It was a facilities management contract. Three-year term, auto-renewal clause with a 60-day notice window. I knew the contract existed. I’d even flagged it when I first organized the repository. But I hadn’t set an alert, because at the time (Read more →)
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Last year I sat in a meeting where our VP of Sales waved a contract at me and said, “Dave, this vendor is saying we owe them for an extra year. Is that right?” I pulled up the agreement. The auto-renewal clause was on page fourteen, paragraph 8(b), buried in a sentence that ran nine (Read more →)
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Six months ago, I started a project I’d been putting off: going through every vendor contract in our repository that involves any kind of AI or machine learning functionality and checking what the agreements actually say about it. Sixteen contracts. SaaS platforms, analytics tools, an HR screening product, a couple of document processing services. All (Read more →)
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Last year, I sat through a webinar where a vendor described their contract management platform as “an end-to-end digital transformation solution for the modern legal enterprise.” I looked at the demo. It was a searchable database with alerts and some reporting. Which is great. That’s what I use every day. But calling it a “digital (Read more →)
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I need to say something that might surprise you, coming from a guy who writes about contract management software for a living: your spreadsheet is probably fine. If you have 30 contracts, a decent Excel tracker, and the discipline to open it every Monday morning, you’re doing better than a lot of people I’ve met (Read more →)
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I’ve been doing contract management for over fifteen years, and for most of that time, nobody above my direct manager cared what was in the contracts database. As long as nothing blew up, the data quality of our contract records was my problem and mine alone. That’s changed. In the last two years, I’ve been (Read more →)










