About the authors

Chris Young

Ironclad General Counsel

Damon Mino

Ironclad Vice President of Sales

Dealbreaker to Dealmaker: Powering the Sales & Legal Partnership

By Chris Young, Damon Mino

Reading Time: 5 minutes


If you work in Sales or Legal, chances are the end-of-quarter crunch is a scenario you likely know entirely too well. It’s a mad dash to the finish line — closing deals, meeting quotas and driving revenue.

Unfortunately, the quarter-close hustle can put unnecessary strain on the relationship between Legal and Sales. Deal and contract status and rapid-fire communication can result in a lack of clarity, constant status updates and frustration. At best, the scenario is a chaotic sprint but the deals get done. At worst, Sales and Legal work in silos with little transparency, viewing each other as roadblocks instead of partners in shared success.

The good news is that a productive sales quarter-end doesn’t have to be this way. At Ironclad, I’ve worked hands-on with Damon Mino, our Vice President of Sales, to align our teams around shared processes, organization and technology.

And that’s why Damon, who spent years as an in-house attorney before transitioning to Sales, and I wanted to create this guide. Over the course of this playbook, you’ll get a glimpse of the common pitfalls in the relationship between Sales and Legal, how to address them and proven best practices you can use to set your company for success.

Aligning Resources

Every General Counsel knows that today’s legal teams are being tasked to do more with less. At the same time, sales organizations are being pushed to move faster and faster. Inevitably, something’s gotta give, right? Not necessarily.

At Ironclad, our situation is a little unique. Damon is a former lawyer who transitioned over to Sales. Given his background in law, he has an insider’s perspective into both sides of the Sales/Legal equation. He’s felt firsthand the intense stress as Sales tries to track contract redlines at the tail-end of the quarter.

And there’s one thing we’ve learned from each other. Neither one of us ever wants to ask, “Who knows if this deal is ever going to get done?”

Damon and I quickly realized that it’s a lot easier to keep things moving in the right direction — and in sync — if we discuss our available resources and how to best optimize them. Fundamentally, this starts with planning.

Here’s how we approach aligning Sales and Legal:

  • Understand the risks of siloing Sales and Legal. Having these teams operating independently from each other is a recipe for chaos and, inevitably, disaster. Inefficient use of legal resources slows the sales process, contributes to frustration and increases outside counsel costs. Legal inevitably becomes a bottleneck and sales reps find workarounds to get their deals done. And who could blame them?To help avoid congestion and frustration, Ironclad’s legal team participates in Sales’ quarterly business reviews. Doing so provides both teams the opportunity to discuss pending or developing deals and prioritize Legal’s time.
  • Plan to anticipate volume. High contract volume is a surefire cause of legal bottlenecks. Our Sales and Legal teams keep open lines of communication and understand the expected pipeline goals, which allows Legal to ramp up and support Sales. Such support can include shifting priorities or standardizing contract terms.
  • Optimize together. Quarterly reviews aren’t just beneficial for sales teams. Together, Damon and I review the previous quarter’s data and adjust discount ceilings accordingly or review friction points to decrease deal cycles. These adjustments impact both teams, and should be approached as a point of discussion and a chance to identify and implement efficiencies.

Getting Granular With Data

Beyond fostering a culture of collaboration and open communication, there’s one thing that empowers our sales and legal teams to drive revenue even in a crunch — data. Thanks to Ironclad’s digital contracting platform, Damon and I have clear, realtime insights into where deals stand in the approval process. Supplemented by data from a CRM, we can further anticipate deals that are likely to close and how to best facilitate them, reducing the stress of tight turnarounds.

For us, working within Ironclad gives us the technical structure to:

  • Leverage data. The most fruitful and meaningful conversations between Sales and Legal should start well before a quarter crunch — and they should rely on data to advise leadership. We base conversations on available data, from Salesforce or a digital contract contracting platform, so both teams can optimize for efficiency. For example, our legal team can demonstrate how much faster deals close when processed on our company’s own paper versus third-party paper.
  • Aim for accountability. Strong executive relationships are also founded on empathy. Damon and I often speak candidly with each other about challenges, expectations, processes and protocols for our teams. This way, we are aligned and able to hold our direct reports accountable.Manual contracting processes require deep dives into details, writing time-consuming emails, repeating and summarizing all the relevant points, all of which soaks up valuable time. With a digital contracting platform, all necessary context is instantly available. The latest redlines, key terms and language are all there in easy-to-review audit trails, from the beginning of the deal. p
  • Get all hands on deck. One of the essential responsibilities of an executive is rallying those around you. At Ironclad, we focus on encouraging our team members to contribute to planning sessions and we work to remove roadblocks on business or product decisions to better facilitate participation.The more Legal can partner and collaborate with Sales, the more empathy you build. When Sales and Legal trust each other, they’re not going to avoid each other. Instead, you can address issues together as you both help the company avoid undue risk.

Striking the Balance Between Speed and Compliance

Every business wants to move as quickly as possible — especially when it comes to sales. On the other hand, every legal team knows that speed increases risk and opportunity for error. So how do you balance the two?

At Ironclad we’ve found that establishing a mix of organizational best practices and implementing key technology can help facilitate ideal outcomes. Our tactics include:

  • Review and prioritize. We take a close look at tiers of terms and conditions, bucketing them into categories of “deal killer,” “important,” “preferred” and “nice-to-have.” This, along with the context of deal size, timing in the quarter and other factors, helps us get on the same page regarding deals.
  • Invest in technology. Ironclad’s digital contracting platform helps ensure our alignment, transparency and compliance. Ironclad gives us instant access to the contract data that drives deals. The trends and analyses based on this data, in turn, drive powerful partnerships with Sales and keep things ticking year-round. Even better, Ironclad enables self-service sales contracting — e.g., developing a sales contract from a CRM — to help get deals done quickly within guardrails set by the legal team.


Legal is evolving faster than ever before. We have new tools at our disposal and the opportunity to demonstrate value across our businesses. But the first step in doing so is to strategically align with other core business functions — especially Sales. Ironclad isn’t immune to the challenges surrounding Sales and Legal partnership. By working together, focusing on training and operating with a mind for continual improvement, Damon and I have helped build a culture that doesn’t just mitigate the end-of-quarter crunches, but supports collaborative, meaningful teamwork across Sales and Legal year round.

It’s our hope that this guide can shed some light on the intricacies of building collaborative Sales and Legal teams. Every organization has different goals, but by following this core framework, you can make significant strides toward fostering collaborative teams that share in each other’s successes and are fully vested in driving revenue.