Contract Intelligence: 3 Lessons from SpotDraft’s Legal & AI Experts

Anjali Pillai
By 
Anjali Pillai
•
Sep 29, 2026
•
3 min
Anjali Pillai is a Marketing Manager at SpotDraft, building content engine that moves beyond traffic to drive real business impact. Her work sits at the intersection of storytelling, organic reach, and revenue—helping B2B SaaS teams turn content into a competitive advantage.
Contract Intelligence: 3 Lessons from SpotDraft’s Legal & AI Experts

TL;DR

  • Measure business impact, not contract volume.
  • Secure AI access based on contract sensitivity.
  • Give AI context-rich prompts, not vague questions.
  • Bring legal into deals earlier.
  • Use AI to turn contracts into actionable insights.

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What three SpotDrafters told a room of in-house lawyers when Crafty Counsel handed them the mic

Last week, three dynamic individuals building the future of legal at SpotDraft came into a room with Crafty Counsel's in-house legal community, to answer some of the most pressing questions around contract intelligence (add something here that simplifies contract intelligence). Vimal Stan Steven (Senior Director, Product) builds the product. Jaskaran Bhatia (AI Product Manager) builds the AI inside it. Karthik Rai (Associate Counsel | Legal) is the lawyer who has to trust both of them. An hour of unscripted Q&A later, here's what came out of putting product, AI, and legal in the same hot seat.

One question set the tone for everything that followed: why does legal still get treated like the department that says no right before a deal closes — and whose fault is that, really?

Legal's real branding problem

Nobody outside legal knows what legal actually does until something goes wrong. That's not a perception problem lawyers can fix with better communication skills. It's a measurement problem.

"Nobody in finance cares that you reviewed 200 contracts last quarter. They care that a deal closed three days faster, or that you caught a liability clause that would've cost seven figures." Vimal Stan Steven

Contract volume is an easy number to report and a useless one to lead with, it tells the business you were busy, not that you mattered. Deal velocity and dollars protected tell a different story, and it's the one finance and the C-suite actually track.

Timing compounds the problem. Show up after commercial terms are already locked, and you're reacting by definition, and reacting reads as a cost center, no matter how sharp the catch. The fix isn't a better redline. It's getting into the room before the terms are set, so the win is visible as strategy instead of damage control.

Cutting it down hard:

Why "just restrict the folder" doesn't work anymore

Locking the folder protects the document. It doesn't protect you once AI is answering questions across your whole corpus, the problem Jaskiran spends his day on.

No file has to change hands to leak. One good question does it.

The fix: permission by contract type, not file, M&A, disputes, exec comp, walled off and logged. Simple. Rarely done.

Treat AI like a junior associate, not a search bar

This is the one worth pinning above your desk and it hits differently coming from Karthik, the actual lawyer in the room.

Type "Liability Cap: the liability cap" and you've told the AI nothing it didn't already know. It doesn't know which document, which section, or what to do when the contract's uncapped so it guesses.

Now try: "the maximum amount the Supplier is liable to pay the Customer for damages, found in the Limitation of Liability section, output as a number, 0 if uncapped."

Same question, but now it's got parties, location, and the edge case covered. That's the whole gap between a prompt that fails silently and one you can actually trust — basically the difference between telling a junior associate "handle it" and giving them a real brief.

The takeaway

Three sharp minds, one hour, zero fluff, product, AI, and legal, each looking at the same problem from a different seat and landing on the same conclusion: measure outcomes instead of volume, permission by category instead of by file, and brief your AI instead of querying it.

That's the kind of conversation SpotDraft shows up to have with the Crafty Counsel community — and it's one worth having inside your own legal team too.

Frequently Asked Questions

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