Why Your ROI Story Falls Flat With Leadership

Every legal leader has heard the promise: implement a CLM system or AI-powered tool, and watch your contracting function transform overnight. Faster deals. Lower costs. Better visibility. Yet, months after rollout, many teams are still asked the same uncomfortable question by the CFO: So, what’s the ROI?

That’s the problem. Estimating the ROI of contract efficiency is notoriously hard to make tangible. Legal teams juggle competing demands every day: accelerating deal velocity, managing risk, and aligning with business goals. But which of these outcomes can be measured in a way that proves ROI?

Lucy Bassli, founder of InnoLaw Group and former Assistant General Counsel of Contracting and Legal Operations at Microsoft and Operations, argues that the key is to start with a specific pain point, not with deploying technology. Akshay Verma, who built world-class legal operations teams at Meta and Coinbase and now serves as COO at contract management platform SpotDraft, believes ROI only becomes real when improvements are tied directly to business metrics and tracked systematically.

Together, they outline a path for turning contract efficiency into measurable ROI.

The Pain Point-First Philosophy

Lucy: I’ve watched countless teams rush into buying technology without first identifying where the problems actually lie, and I can tell you this with certainty: you have to start by asking, “What’s the single biggest problem driving your interest in CLM or AI for contracting?” There has to be a specific pain you’re trying to alleviate. Are contracts taking too long to close? Are risks handled inconsistently? Are obligations going unnoticed post-signature? Without this clarity, it would be impossible to determine what ROI your team is chasing. The vendors will promise you everything, but unless you know exactly what problem you’re solving, you’ll never be able to measure whether you’ve actually solved it.

Akshay: The first thing I had to understand when I was building legal ops at scale was: what were my goals for efficiency? What was the problem I was trying to solve in contracting? Because here’s the thing, these problems generally fall into four main categories, and each one demands a different approach. First, there’s deal velocity: delays in contract cycles that directly affect revenue. Then risk calibration, where overlawyering slows deals down while underlawyering creates regulatory and litigation exposure. Third is visibility, where leaders need to see at what stage contracts are in the workflow and track renewals and other key obligations post-signature. And finally, enablement. If legal is reviewing every single contract in the organization, there needs to be a fundamental shift in the way legal works. This takes up a massive chunk of bandwidth and prevents legal from focusing on strategy and high-risk contracts. Each of these pain points, when improved, delivers measurable business value. But you have to know which one you’re targeting.

Translating Pain Into Metrics That Matter

Lucy: Once the pain point is defined, it must be mapped to metrics. This is where most teams stumble. ROI begins with aligning measurement to the business outcome you’re after. If cycle time is the problem, measure days-to-close. If visibility is lacking, measure usage of dashboards or compliance with renewal tracking. But here’s what’s critical: metrics should grow with the business. What’s relevant for a 100-person company may be completely irrelevant for 400 employees. The ROI framework must evolve continuously, or you’ll find yourself measuring things that no longer matter while the business has moved on to different priorities. Measuring too many data points gets overwhelming and meaningless. Focus on what matters.

Akshay: In legal ops, I spent years turning each pain point into a relevant metric that directly shows whether contracting is getting efficient and how it’s adding value to the business team. Some key metrics I tracked: contract cycle time end-to-end, percentage of legal requests resolved without escalation, time spent on non-strategic versus strategic work, adoption rates of tools and processes, and legal spend efficiency comparing internal versus external resources. The truth is, making data-driven decisions is sorely lacking in law. But when legal ops tracks the right data, ROI becomes visible in ways that even the CFO can’t ignore: faster revenue recognition, lower legal spend, and more time for strategic work. Suddenly, you’re not just a cost center anymore. You’re contributing to the bottom line in ways that can be quantified.

The Business Alignment Imperative

Lucy: Let me be blunt about something that too many legal leaders overlook: there is no reward in-house for the time spent lawyering. We become in-house lawyers to support the business. And when struggling with contracting remember – CLM tools are not silver bullets. They amplify whatever processes exist, good or bad. That’s why I urge legal leaders to work hand-in-hand with business stakeholders before implementing technology. Efficiency only matters if the business feels it. You need to clarify which contracts business teams can sign without legal review and which require escalation. This avoids wasting legal bandwidth on low-risk agreements like NDAs or low-value deals while keeping guardrails where they count. If the business doesn’t understand where they can operate autonomously and where they need to pull in legal, you’ll continue to be the bottleneck no matter what technology you deploy.

Akshay: Exactly. Why are we looking at every single contract? Can we enable the business more? A simple way to solve this is to create monetary thresholds. For example, no review needed below $25K, and codify escalation rules to guide business autonomy. Add acceptable deviations to clauses so the business knows where they can deviate and avoid escalation to legal.

This is where legal ops must look at the number of low-value contracts that come to legal and how much time they take to close. Such contracts are usually high in volume, so taking them off legal’s plate saves significant time and also helps business close them out faster. Such ruthless prioritization of legal’s and business’s time clears the fog, and suddenly we start to see the ROI materialize in ways that weren’t possible when legal was trying to review everything.

From Operational Efficiency to Strategic Advantage

Lucy: Here’s what people need to understand: contracts are business lifelines. Every sale, every partnership, every vendor relationship flows through them. When contracting is handled inefficiently, the business bleeds time and loses opportunities. But when legal shifts from firefighting to structured, disciplined contracting, the impact is immediate and visible: faster sales cycles, smoother supplier onboarding, fewer costly renewal surprises. Now, it’s important to remember that ROI in contracting rarely shows up in a single big win. It’s the sum of dozens of smaller, compounding improvements. A week shaved off every contract cycle means revenue hits the books sooner. Standardized playbooks reduce disputes and renegotiations. Better tracking of obligations avoids penalties and ensures compliance. Over time, these operational wins elevate legal from a reactive function to a trusted business partner.

Akshay: Let’s take this idea one step further. To me, efficiency is only the starting point; the real value is when legal begins to “run like a business.” That means applying the same rigor that sales or finance uses: tying improvements to measurable KPIs, aligning closely with leadership priorities, and reporting on progress in terms the business understands. When this happens, ROI isn’t just about cost savings or time reductions. It becomes a growth story. Predictable cycle times mean revenue forecasts are more accurate. Strategic bandwidth freed from low-value contracts allows legal to focus on negotiating better deals. Stronger visibility into obligations strengthens relationships with both customers and vendors. I see legal operations moving from a defensive posture, focused on compliance and cost, to an offensive one, where legal is actively enabling revenue, improving margins, and shaping business strategy. ROI, then, isn’t just a static number. It’s proof that legal has become a strategic driver of business success.

The Path Forward

The ROI of contracting isn’t found in glossy CLM dashboards or after-the-fact reports. It shows up in the margins: when a contract closes a week faster and revenue hits the books sooner, when legal no longer spends hours on low-value NDAs, and when business leaders can see obligations at a glance.

Lucy and Akshay’s framework is deceptively simple: identify the pain, measure it, align with business, and refine. Do this, and ROI stops being a theoretical puzzle. It’s tangible proof that legal is no longer a back-office function; it’s a growth partner sitting at the table.