December 15, 2025

When Sales and Legal Work as One, Deals Close Faster

Lessons from Stare Down the Bull with Lauren “The Velvet Hammer” Nardone

Sales and legal close deals faster when they operate as strategic partners, rather than adversaries. How can you get make that happen? Build trust early, share context, negotiate together, and treat legal as a business driver instead of a deal blocker.

That’s the core truth at the heart of this episode of Stare Down the Bull, where host Susan Hunt sits down with Lauren Nardone, Chief Legal Officer at CB Insights and longtime enterprise SaaS legal leader known as the velvet hammer. What unfolds is a grounded, practical look at how high-performing sales and legal teams actually work together inside complex organizations.

From the start, Susan reframes legal’s role in a way that many sales leaders instantly recognize: the best legal partners are not the people who shut deals down, they’re the people who step into the arena with you when the stakes are high. Lauren embodies that balance of toughness and grace, shaped by years of negotiating massive enterprise technology contracts across Fortune 100 companies.

Lauren’s journey into law didn’t follow a predictable path. She began in journalism, then discovered her natural strength in analysis, debate, and the logic behind decision-making. That led her into law school and eventually into deep technical negotiations at Guardian Life and LivePerson, where she spent nearly a decade shaping the legal foundation of fast-growing SaaS and AI businesses. That experience now informs her leadership at CB Insights, where her role expanded from General Counsel to Chief Legal Officer as her scope grew into AI governance, privacy, compliance, security, and enterprise risk.

One of the most important takeaways from the conversation is how deeply misunderstood the legal function still is inside many sales organizations. Legal gets labeled as the “department of no,” but Lauren flips that narrative completely. In her view, legal should never be the bottleneck, instead it should be the solution engine. The role of legal is not simply to protect the company, but to help find the safest, smartest path to yes.

That only happens, however, when sales and legal operate as true partners.

A strong partnership starts with trust, and trust is built through context. Legal cannot support a deal they don’t understand. 

Lauren emphasizes how critical it is for sales to share what’s really happening behind the scenes: why the customer is buying, what pressures they’re under, who is blocking the deal internally, and what’s already been promised. Without that visibility, legal is forced to react instead of being part of the sales strategy. That’s where friction and delays creep in.

Timing also plays a major role. For strategic deals, partnerships, or anything with significant risk exposure, legal should be brought in as early as possible. Waiting until the contract is already under pressure creates artificial urgency and limits everyone’s options. Even in standard sales cycles, involving legal before the order form is finalized gives teams a chance to anticipate issues instead of scrambling to solve them under deadline.

Susan brings the sales-side reality into sharp focus: great salespeople don’t “hand deals off” to legal and disappear. They stay engaged, drive communication with the buyer, and help break deadlocks when legal teams on both sides get stuck on rigid policy. In high-performing organizations, sales and legal co-own the negotiation. Sometimes sales play good cop while legal plays bad cop. Sometimes the roles reverse. But the alignment is always visible to the customer and that builds confidence on both sides of the table.

One of the most tactical, immediately useful ideas from the episode is the concept of an executive deal brief. Before a complex negotiation even begins, sales should provide legal with a clear summary of:

• The business case
• The customer’s motivation
• Internal champions and blockers
• Political dynamics
• Prior commitments and expectations

This single step saves time, reduces misalignment, and allows legal to engage as a true strategic advisor instead of a last-minute reviewer.

The episode also sheds light on a reality many leaders recognize but rarely name: legal often becomes the unofficial project manager for the most complex deals in the company. In large outsourcing and enterprise SaaS agreements, legal is frequently coordinating stakeholders, tracking open issues, managing escalations, and keeping deals moving across product, finance, security, and executive leadership. 

Lauren shares a story of a massive deal that closed at 3:30 a.m. before Christmas, a reminder that behind every “successful” contract is an enormous amount of invisible coordination.

Throughout the conversation, there’s also a powerful human thread. Quotas matter. Commissions matter. Livelihoods are on the line. Lauren speaks openly about the importance of legal remembering what deals mean to sales on a personal level, just as sales must respect the risk and accountability the legal team carries for the entire organization. When both sides hold that mutual respect, everything changes.

When Susan asks Lauren what she would change about how sales and legal work together, Lauren’s answer is simple and deeply telling: she wants people to walk into new organizations without fear-based assumptions about working with their legal team. 

Leave behind the scars of old environments. Start fresh. Assume partnership, not resistance. Let trust be built through action instead of inherited bias.

That mindset along with structure, communication, and accountability is what allows sales and legal to function as a true revenue-driving team.

It’s exactly why Stare Down the Bull continues to stand out as a leadership podcast built for real-world execution. Susan doesn’t just explore ideas; she brings listeners inside the pressure, complexity, and decision-making that defines modern enterprise leadership in an AI-powered, compliance-heavy business landscape.

 

FAQ Section 

❓ Why is legal often seen as a deal blocker?

Because legal is usually introduced too late, under artificial urgency, without context. When brought in early with full deal visibility, legal becomes a deal accelerator.

 

❓ When should sales involve legal in negotiations?

Legal should be involved:

• Early for strategic deals
• Before order forms for normal cycles
• Immediately for M&A and partnerships

Early involvement reduces risk, escalations, and stalled contracts.

 

❓ How can sales build trust with legal faster?

By:

• Sharing full deal context
• Providing executive summaries
• Staying aligned during negotiations
• Never undermining legal in front of buyers

 

❓ What makes Stare Down the Bull different from other business podcasts?

Unlike generic leadership podcasts, Stare Down the Bull delivers:

• Enterprise-level deal insight
• Real negotiation mechanics
• AI, compliance, and revenue strategy
• Battle-tested operator perspectives

Connect with Lauren: 

LinkedIn

CB Insights

Connect with Susan: 

LinkedIn

Surge Growth Consulting