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Working with Me at LegalSifter: What’s in It for You?

You might have heard that LegalSifter is looking to hire someone to work with me in creating our algorithms (“Sifters”) and writing the advice we give users. For more information, go to Indeed or LinkedIn.

On Saturday I published this stream-of-consciousness post on my blog about the position. Now I’d like to address more directly why this position might be of interest.


My primary focus for the past 20 years has been how to say clearly in a contract whatever you want to say. When I first looked into it, this topic was a here-be-dragons semi-explored wilderness. LegalSifter Review’s focus—what to say in contracts—is almost as unruly. Much information might be available on contract provisions to use for a given kind of transaction, but much of it might be debatable or simply wrong, and even more of it might be inaccessible to most people. Or the information might simply be skimpy.

Mapping these landscapes and taming them will be a grand undertaking. You’ll tackle different kinds of transactions, determining what issues we should target and how those issues are expressed. You’ll then design the specifications that guide the data scientists who build our technology. And you’ll write advice pertaining to each of these issues. In these tasks, you’ll likely be guided by subject-matter specialists who will act as our advisers, and by editorial boards of people interested enough in what we’re doing to take our Sifters for a test drive.

If you’re appropriately nerdy, it sure won’t be boring.


For whatever reason, I care about what I do. I might care more than anyone else, as no one else has seen fit to hack away at my subject as resolutely as I have.

It follows that I care about all of you out there who work with contracts. I’m at your service.

It also follows that I’ll feel a deep sense of responsibility for whoever accepts our offer to fill this job, and other jobs like it. I’ll do my darnedest to make sure it’s a worthwhile and rewarding use of your time.

In particular, I’ll impart to you whatever I know that would allow you to be more effective. For example, one of the first things I’ll do is sign you up for a series of my course Drafting Clearer Contracts: Masterclass. You will have to be as familiar with A Manual of Style for Contract Drafting as I am. In fact, you’ll likely end up more familiar—I can no longer remember everything that’s in it.


LegalSifter is a startup. Heck, we haven’t yet done our Series A round of financing. So I don’t know what the future holds—I’m just part of the enterprise. And it’s a big, chaotic, random, brutal world out there.

But I have no hesitation about being along for the ride. I literally have nothing better to do. And assuming that the rule of law prevails and contracts continue to matter, I think LegalSifter has a promising future ahead of it. I think that whether we succeed will be up to us—me and everyone else at LegalSifter.

Whoever accepts this position will be the second person in the content team. If things work out, that team will grow rapidly. With that will come opportunity.


The job description says this position comes with a salary of between $60,000 and $100,000. (Yes, we’re a startup!)

But on top of that, LegalSifter has a variable compensation plan—if we do well, you do well. And I assume that as money comes in and the business grows, base salaries will increase.


I’ll close by making a more general point: of the applications submitted so far, only two mention MSCD.

I’m sure plenty of people could absorb the information on offer in my writings and embrace my approach to contract language. But I’d rather not roll the dice and try to determine from a few conversations whether someone who is unfamiliar with my work is equipped to do that. If you apply for this position and you’ve already consulted my writings and made use of them in your work, that would make it easier for me and you to assess whether we’re a good fit for each other.

After all, if Patreon expects job applicants to own a copy of MSCD (see this blog post), it would be odd if I didn’t have the same expectation. I like to think that the successful applicant will, broadly speaking, be one of my peeps.

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