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Ask any GC or legal ops manager where deals slow down, and you'll get a version of the same answer: legal is the bottleneck. The contracts sit on someone's desk. Things fall through the cracks. The sales team is frustrated. Sound familiar?
That narrative is both pervasive and, in many cases, just wrong.
In a recent SpotDraft webinar, Rick Estacio (Senior Director and Deputy GC, Reddit), Sarah Binder (GC, BetterUp), and Kim Humphrey (Legal Operations Manager, BPP) shared what it actually looks like to build a contracting engine that moves at business speed. What emerged was less a set of tool recommendations and more a mindset shift, one that starts long before any software gets procured.
Rick's first move at Reddit was the same as his last few stops: get the data. Not just cycle time from kickoff to signature, but a breakdown of every step — how long drafts sat with the counterparty, where internal approvals created sequential waits, which deal types ran long and why.
"We sent the draft back in two hours. Then it was four weeks before we heard anything. We could finally show the business: the bottleneck wasn't us." - Rick Estacio, Deputy GC, Reddit
That kind of visibility changes the conversation with business partners entirely. It shifts the question from "why is legal slow?" to "who has the ball, and for how long?" The same principle holds internally: parallel approval tracks will always outpace sequential ones but only if you know where the handoffs are happening.
Kim's path to this visibility was less glamorous. No new tools, just Power Query pulling email data, codified into a rough business case. Sometimes that's what it takes to get the budget for something better.
Once you have a system, any system, data hygiene becomes the unglamorous work that determines whether it's actually useful. Sarah was unequivocal on this point: get your senior legal leadership aligned on nomenclature, tagging, and document classification before you build anything around it.
"If all your order forms are tagged as amendments — which obviously I've never done — it doesn't really help." - Sarah Binder, GC, BetterUp
This isn't just a legal ops concern. In 2026, it's an AI concern too. AI tools don't create good data where none exists. The quality of any AI-assisted contract workflow is a direct function of the data quality underneath it; which means the cleaning work has to happen before, not after, any major tooling investment.
Kim made an observation that cut through the noise: we're halfway through a 2026 webinar on legal ops, and no one has used the word "playbook." That's meaningful. The discourse has shifted from rigid, clause-by-clause negotiation scripts toward something more contextual, a framework built around the business's actual risk appetite.
What does that look like in practice? Sarah runs deals desk and procurement alongside her GC function, partly because she found that treating commercial execution as a unified process, rather than a legal handoff, gave her team far more control over velocity. Rick built review thresholds by deal type, dollar value, and risk level creating lanes where legal doesn't need to be involved at all.
The goal isn't to remove legal from the picture. It's to make sure legal's involvement is proportionate, well-timed, and additive, not a tollgate that slows everything down.
Month 1: Inventory the current state Map every contract type, who touches it, and what the process actually looks like, not what you think it looks like. Document what exists before trying to improve it.
Month 2: Listen before you fix Talk to your stakeholders — legal team and business alike. Don't skip ahead to solutions. You might be fixing something the business doesn't consider broken, or missing the thing that actually matters.
Month 3: Challenge everything Go back to everything you learned in months one and two with one question: is this the right way to do it, or just the way we've always done it? That tension is where real process improvement lives.
One final note worth carrying into any change initiative: an average process that 98% of your team actually uses is worth infinitely more than a perfect process that gets routed around. Build for adoption first. The sophistication can come later.
Interested in attending more webinars by SpotDraft? Keep an eye out here.
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