By Matt Darling, LegalSifter

You know what kills deals? Time.

Not price objections. Not competitor pressure. Not even budget freezes. It's the slow, agonizing crawl through contract review that turns hot opportunities into cold losses.

Here's a stat that should make every CRO lose sleep: 74% of deals stall in the late stages. That's not a lead gen problem. That's not a pipeline problem. That's a "waiting on legal" problem: and it's bleeding your revenue dry.

Let's talk about how to fix it.

Key takeaways

• Deals don’t stall because buyers lose interest—they stall because contract negotiations create friction late in the sales cycle.
• “Waiting on legal” is usually a capacity problem, not a performance problem, and it becomes worse as revenue teams scale.
• Most contract redlines are repetitive and should be systematized through a legal playbook, not handled manually deal after deal.
• AI contract redlining software helps sales teams apply attorney-approved positions instantly, directly inside Microsoft Word.
• The result is faster deal velocity, more consistent risk management, and legal teams freed up to focus on truly complex negotiations.

Why Deals Stall in Contract Negotiation

Every day a deal sits in legal purgatory is a day your competitor has to swoop in. It's a day for your champion to lose internal momentum. It's a day for that budget to get reallocated somewhere else.

Time kills deals. Full stop.

But here's what most CROs miss: the cost isn't just the deals you lose outright. It's the deals that do close: but take 30, 60, or 90 days longer than they should. That's:

• Delayed revenue recognition that throws off your forecasts

• Extended sales cycles that inflate your CAC

• Rep frustration that tanks morale and increases turnover

• Opportunity cost from reps babysitting stalled deals instead of opening new ones

And the culprit? More often than not, it's contract redlining.

Your sales team sends over the agreement. Legal gets to it when they get to it. Redlines go back and forth. Weeks disappear. The deal that was "closing this quarter" suddenly isn't.

Sound familiar?

The Revenue Impact of “Waiting on Legal”

Let's be honest: your legal team isn't the enemy here. They're swamped.

Most in-house counsel spend 60–80% of their time on contract review. They're buried in NDAs, MSAs, and order forms while also handling compliance, IP issues, and a hundred other fires. Your deal? It's in the queue.

The problem isn't effort. It's capacity.

When every contract requires manual legal review, you've created a bottleneck that scales with your success. The more deals your sales team brings in, the longer the wait times get. Growth becomes its own punishment.

And here's the kicker: most of those redlines are the same ones your GC has made a thousand times before. The same indemnification tweaks. The same liability cap adjustments. The same data protection language.

Your legal team is doing repetitive, high-stakes work that should have been systematized years ago.

What Is AI Contract Redlining Software?

Every good legal team has a playbook: a set of pre-approved positions, fallback language, and deal breakers that define what's acceptable and what isn't.

The problem? That playbook lives in your GC's head. Or buried in a SharePoint folder. Or scattered across dozens of marked-up Word docs that nobody can find when they need them.

Your sales reps don't have access to it. Your deal desk doesn't have access to it. So every single contract goes back to legal for review, even when the answer is already known.

This is where AI contract review tools change the game.

Imagine if you could take your General Counsel's brain: all those pre-approved positions, all that institutional knowledge, all those "here's what we always change" insights: and put it directly into the hands of your sales team.

AI contract redlining software helps revenue teams close deals faster by automatically applying attorney-approved contract edits, reducing negotiation cycles without increasing legal risk.

That's exactly what LegalSifter ReviewPro does.

How LegalSifter ReviewPro Works Inside Word

ReviewPro is an AI-powered contract redlining and review automation tool that applies your legal playbook directly inside Microsoft WordReviewPro is contract redlining software that works directly inside Microsoft Word. No new platforms to learn. No clunky interfaces. Just intelligent, attorney-quality redlines applied in seconds based on your company's specific playbook.

Here's how it works:

1. Your legal team defines the playbook. What language is acceptable? What requires pushback? What's a deal breaker? All of it gets encoded into ReviewPro.

2. Your sales team receives a contract. Instead of forwarding it to legal and waiting, they open it in Word and run ReviewPro.

3. ReviewPro analyzes the entire agreement. It identifies deviations from your standards, flags risk areas, and suggests pre-approved redlines: all in the time it takes to grab a coffee.

4. Your rep sends back attorney-quality redlines. No waiting. No bottleneck. No crossed fingers hoping legal can squeeze it in before quarter-end.

The result? Deals that used to take weeks to negotiate now close in days. Your legal team focuses on the genuinely complex issues instead of rubber-stamping routine contracts. And your reps stop treating "waiting on legal" as an excuse for slipped deals.

Benefits: Faster Deals + Lower Risk + More Consistency

Here's something that keeps GCs up at night: inconsistency.

When every contract gets reviewed by whoever happens to be available, you end up with different standards applied to different deals. One attorney accepts a limitation of liability cap. Another pushes back hard. Reps learn to "attorney shop" for the most permissive reviewer.

That's not a legal strategy. That's chaos with extra steps.

With contract management software like ReviewPro, every deal follows the same commercial guardrails. The playbook is the playbook: applied consistently, every time, regardless of who's handling the contract.

This does two things:

First, it reduces risk. Consistency means predictability. You know exactly what positions your company is taking across all agreements. No surprises. No "how did we agree to THAT?" moments six months later.

Second, it makes your legal team's life easier. When they know ReviewPro has already applied the standard playbook, they can focus their limited time on the edge cases that actually require human judgment. That's a better use of expensive legal talent: and it's a lot less soul-crushing than reviewing the same NDA for the 500th time.

How CROs Can Remove Contract Bottlenecks

Let's bring this back to what matters: revenue.

The research is clear: deals stall in negotiation. Not because buyers aren't ready, but because internal processes create friction. Every handoff, every review cycle, every "let me check with legal" is an opportunity for momentum to die.

Smart CROs are eliminating those handoffs.

They're tracking where deals slow down, which contract terms cause the most friction, and where teams are making unnecessary concessions just to move things along. Then they're systematizing the solutions.

ReviewPro isn't just about speed. It's about control. Control over your deal cycle. Control over your risk exposure. Control over the consistency of your commercial terms.

When your sales team can self-serve on routine contracts, you've fundamentally changed the equation. Legal stops being a bottleneck and starts being a strategic partner. Reps stop dreading the redline phase and start seeing it as a competitive advantage. And deals that used to drag on for weeks start closing in days.

The Bottom Line

If you're serious about accelerating deal cycles, you have to look at where deals actually stall. For most B2B companies, that's contract negotiation.

You can hire more lawyers (expensive, slow to onboard, and they'll eventually hit the same capacity wall). You can pressure legal to work faster (good luck with that). Or you can systematize the process with AI-powered contract redlining software that replicates your legal team's expertise at scale.

LegalSifter ReviewPro gives your sales team the power to apply attorney-quality redlines in seconds: directly inside Microsoft Word, based on your company's specific playbook. No new platforms. No waiting. No more "deal held up in legal."

Just faster closes. Lower risk. And a sales team that finally stops blaming legal for missed quarters.

Ready to see how fast your deals could actually close? Let's talk.

FAQs

About Matt Darling

Matt Darling, Head of Revenue, is a seasoned SaaS revenue leader with a track record of building high-performing teams and driving sustained growth. At LegalSifter, Matt leverages this experience to help legal and business teams simplify contract review, reduce risk, and accelerate deal cycles with AI-powered solutions.