How to Strengthen the Sales–Legal Relationship to Speed Deals

If you’ve ever heard a sales rep say “legal is slowing down my deal” or a lawyer say “this came in with zero context,” you’re not alone.

Last week, I had the pleasure of co-hosting a webinar with Chris Dunsford (Vice President, Applications @ Element Technologies) where we unpacked this exact challenge: how to strengthen the relationship between sales and legal teams to move faster, without taking on unnecessary risk.

Whether you’re in sales trying to hit quota, or in legal trying to keep the business out of trouble, you’ve probably felt the pain of internal friction. So, let’s recap some of the most insightful takeaways from that conversation, along with a few practical ideas for how to close deals quicker, together.

Sales and Legal Are on the Same Team: Why Does It Feel Like a Tug-of-War?

Sales and legal teams want the same outcome which is to close good deals both quickly and confidently. But in practice, it can feel like everyone’s pulling in opposite directions.

Sales is moving at the speed of the buyer. They’re thinking about hitting numbers, building relationships, and keeping momentum. Legal, on the other hand, is focused on protecting the business by managing risk, ensuring compliance, and maintaining consistency. Neither side is wrong, but when those priorities aren’t aligned, the process breaks down.

In the webinar, Chris put it perfectly:

‍“Both teams crave the same thing: a predictable path to a signed deal.”

‍And I couldn’t agree more. The problem isn’t that legal wants to say “no” or that sales is being reckless. It’s that the process between them isn’t built for collaboration.

But don’t worry. That’s fixable.

Where the Relationship Breaks Down

Sales says, “Where’s my contract? Why is this taking so long?”

Legal says, “You sent this over with no context and 30 other things on my plate.”

One of the biggest blockers we see is the way requests come into legal: Slack messages, random emails, verbal chats in the hallway. There’s no standardization, no prioritization, and no audit trail. It’s what Chris called “shadow processes” and when everything’s invisible, everything becomes urgent.

Then there’s the misalignment around risk. Sales might see a fast signature as a win. Legal sees a redline with unclear terms and hears alarm bells. Without a shared understanding of what’s “low risk” vs. “high risk,” every deal gets slowed down by back-and-forth, reviews, and approvals (even when it doesn’t need to).

So, the bottom line here is: when intake is messy and expectations aren’t aligned, everyone loses time. And in sales, time kills deals.

The Cost of Inefficiency: Legal Teams Are Stuck in Low-Value Work

One of the most surprising stats we shared during the webinar was this: 1 in 5 in-house lawyer hours is spent on low-complexity, repetitive work. Think about that. Twenty percent of legal’s time is going to tasks that could be automated or delegated instead of into high-impact legal strategy.

In fact, 65% of in-house legal professionals say they feel frustrated by administrative work. This is the kind of work that leads to burnout, backlog, and tension with other teams. Because while legal is stuck reviewing another standard NDA or chasing missing deal details, sales is wondering why it’s taking two weeks to get something signed.

This inefficiency also creates a perception problem as legal gets labeled a blocker. But the legal teams aren’t slow – they’re overwhelmed. And that’s something we can solve.

The Fix: Automate the Intake, Route by Risk

How do we get legal out of the weeds and deals across the line faster? It starts with cleaning up intake and getting smarter about what actually needs legal’s attention.

With Checkbox, we’re seeing legal teams completely transform this part of the process. Instead of sales lobbing half-complete requests over the fence, Checkbox enables structured intake powered by AI so all the critical info is captured up front. No more chasing down deal terms, approvals, or redlines after the fact.

Low-risk requests (like standard NDAs or previously approved playbook terms)? Let those flow through automatically or be handled via self-service. Checkbox can even keep a human in the loop with a lightweight approval if needed.

High-risk or non-standard contracts? Those get flagged and routed directly to legal, with all the context already captured so legal can dive in faster, with fewer cycles.

It’s a win-win: Sales moves fast, legal maintains control, and both sides spend less time chasing paperwork.

Let Sales Work in Salesforce and Legal Work in Outlook

Typically, sales lives in Salesforce. It’s where the pipeline is managed, where deals are tracked, and where momentum is built. Legal, on the other hand, typically lives in Outlook, Word, CLM, and Slack. Forcing either team to adopt a whole new system just to collaborate is a recipe for more friction, not less.

That’s why one of the things I love about how Checkbox is built is that it meets both teams where they already are. Sales can submit requests directly from Salesforce. Legal can work from Outlook, Word, or their CLM, while still getting the visibility and structure they need to manage requests effectively.

Everything stays connected behind the scenes: request status, approvals, deadlines, audit trails. Sales knows what’s happening. Legal knows what’s coming.  

Strengthening alignment between sales and legal is about bridging the gap without breaking habits. And when that happens, the relationship transforms from transactional to collaborative.

When You Align Sales and Legal, Deals Move Faster and Smarter

During the webinar, Chris talked about helping teams move from “overly cautious” or “recklessly fast” to a place of smart, scalable risk. That resonated because the goal is to build a system where the right deals get the right level of oversight, and everything else moves at speed.

Checkbox helps enable both revenue and effective risk management. Whether it’s through AI-powered intake, self-service automation, or integrated approvals, we’re seeing teams get to signature faster without compromising on control.

Key Takeaways

If there’s one thing I hope you take away from this, it’s that the friction between sales and legal isn’t just a people problem – it’s a process problem. And with the right tools in place, it’s one you can actually solve.

If this resonated with you (maybe you’re seeing deal delays, or your legal team is stretched thin), I’d encourage you to check out the full webinar where we walk through real examples, talk strategy, and even demo what this looks like in action with Checkbox.

Ready to jump in and see how Checkbox can help your team move faster without taking on more risk? Let’s chat.