Customer Stories
How MasterClass built a legal team that moves at the speed of the business
Contract Review, Legal Research, and Strategic Enablement
When Kevin joined MasterClass as General Counsel, he inherited a fully remote company, a lean legal team, and a mandate that most legal organizations would recognize: do more with less, and do it without slowing the business down.
MasterClass operates in a consumer environment that is not heavily regulated. But the absence of heavy regulation does not shrink the legal workload or the pace of business. It means the team is expected to be an enabler, not a gatekeeper. Revenue drivers, product launches, partnership agreements, marketing campaigns, research requests that arrive without warning from the CEO's desk: all of it lands with a small team that has no structural reason to say no and every reason to find a solution.
Every question that arrives in a lean legal department carries a hidden cost: the time it takes to find the answer before you can even begin to advise on it. At MasterClass, those questions do not slow down for headcount. The question was what the legal team could actually carry, and what it would take to carry more of it.
Before Ruli, the cost of that research layer was often invisible. After Ruli, it became manageable, enabling the team to shift focus from reactive research and contract review to proactive, strategic counsel and expanding the scope of work they could support.
Legal as a service organization, by design
Kevin’s philosophy about legal has always been clear. “I see legal as a service business,” he says. “It is in service of pushing the business forward. Whether that’s a revenue driver, product growth, or launching new features. Legal is here to enable the business. We’re not just trying to say no. We’re trying to find solutions.”
That philosophy shaped how he thought about building the legal function at MasterClass from the beginning not just the people, but the processes, the tech stack, and the way the team showed up for its internal clients. If legal was going to be a genuine business partner to sales, product, and marketing, it needed the infrastructure to move at that speed.
That meant thinking carefully about work streams. Not just identifying what the team was responsible for, but asking which of those work streams could be improved with technology — and where the right tool could free up the lawyers to focus on the strategic work they were actually hired to do.
“We’re not just trying to say no to the business. We’re trying to find solutions. And so when thinking about building the legal team, empowering them to be that business partner — that’s primarily my goal.”
— Kevin, General Counsel, MasterClass
Starting from the inside out
When Kevin started evaluating legal tech, he began internally, not with the market. He mapped the work streams his team was responsible for, identified where the time was going, and only then looked at what tools could address those specific areas. Two work streams rose to the top:
Contracts
● Turnaround times were something the business could feel directly — a deal delayed is a relationship strained.
● Contract review was consuming time that could be spent on higher-value strategic work.
● The team needed a tool that could redline accurately and live inside the workflows lawyers already used.
Research
● CEO questions about unfamiliar business areas, regulatory considerations outside the team’s core expertise, and novel jurisdictions each carried the risk of pulling a lawyer out of strategic work for hours.
● Routing questions to outside counsel that could be handled in-house meant unnecessary cost and delay.
● The goal wasn’t 100% of the answers, it was enough to ask the right questions and go to the right experts prepared.
“I wanted a tool specific for our legal team,” Kevin says. “Contracts were one element, but research was another. I wanted something that could at least guide us toward the right questions to ask, not necessarily 100% of the answers, but a way of thinking, a way to go to the right experts with the right preparation.”
He evaluated eight tools before landing on Ruli. The decision came down to two things:
● Breadth. For a small legal team covering a wide range of topics, a point solution with narrow functionality was not the answer. The tool needed to address both contracts and research from a single platform.
● Team. For a function that needed to grow, Kevin wanted a partner who would build with him — responsive to feedback, willing to adapt, and invested in where the product was going, not just where it was.
“I love working with early-stage companies because they can build with you. They are more responsive to your feedback, more responsive to your particular needs. And as long as you believe in the team and their vision, it’s great to grow with them.”
— Kevin, General Counsel, MasterClass
The moment it clicked
During the pilot, Kevin was testing Ruli alongside other tools against hard requirements: how well did it handle contract review, how precisely did it identify issues, how did it perform against real documents from MasterClass’s own work streams. But the moment that shifted his thinking was specific.
It was the Word plug-in. Not the concept of a Word integration, but what it actually did inside a document. Rather than marking up an indemnity clause by deleting the entire section and inserting a desired replacement, Ruli read the clause, understood what it was doing, and proposed targeted, precise redlines the way a lawyer would. It understood the structure of the agreement and the logic of the position, and it responded to both.
“It sounds small,” Kevin says, “but seeing the ability to make pinpoint redlines — to go through, identify issues, and propose them in a very specific way as a lawyer would do — that was the clicking moment. Where it felt like this is something that could be useful for my team. And it lives in the world that we lawyers live in, which is Word.”
Hard Requirements
Functional Breadth: The tool needed to handle both contract review and legal research on a single platform, avoiding fragmented point solutions.
Precise Execution: The technology had to perform accurate, targeted redlining within Microsoft Word, mimicking the nuanced approach of a lawyer rather than simply replacing text.
Operational Performance: The tool had to demonstrate high-quality issue identification against the team's real-world document workflows during a pilot phase.
Soft Requirements
Partnership-Oriented Culture: The vendor needed to be a true partner—responsive to feedback, willing to debate reasoning, and invested in long-term product vision.
Collaborative Growth: The team prioritized working with an early-stage company that could build alongside them, adapting quickly to specific needs rather than offering a one-size-fits-all vendor transaction.
The soft requirements confirmed what the hard ones suggested. During the pilot, when Kevin raised issues or identified bugs, the Ruli team responded. They engaged with the feedback, explained their reasoning when they disagreed, and demonstrated that the relationship was a partnership, not a vendor transaction. That responsiveness mattered as much as the product itself.
“Seeing the ability to make pinpoint redlines — to propose them in a very specific way as a lawyer would — that was the clicking moment. It lives in the world that we lawyers live in, which is Word.”
— Kevin, General Counsel, MasterClass
Six months in: faster contracts, more confident counsel
Six months after implementation, the impact at MasterClass was visible in two places: turnaround times and confidence. On contracts, Kevin is direct about what changed. “Things that have taken me two weeks or one week have been reduced to one day or even the same day. It has markedly improved my contract turnaround times.”
Implementation itself was part of the story. Unlike the CLM rollouts of an earlier era — consultants, data migrations, months of configuration before anything was usable — Ruli was functional out of the box. Kevin’s IT team was not a dependency. Legal could run it themselves. The more context and precedent they fed in, the more powerful it became, but the baseline was immediately usable.
On research, the value was harder to measure in hours but no less real. Kevin describes it as a shift in preparedness. Areas outside his core corporate background, questions that would have required a call to outside counsel just to figure out what to ask — those gaps narrowed. “I feel more comfortable asking the right questions to outside counsel using the research functionality,” he says. “The team feels more armed with knowledge and information going into meetings with the business. That has helped us.”
“Things that have taken me two weeks or one week have been reduced to one day or even the same day. It has markedly improved my contract turnaround times.”
— Kevin, General Counsel, MasterClass
The attorney still leads, the team goes further
Kevin is clear about what Ruli does and does not change. The legal judgment, the strategic advice, the accountability — those stay with the lawyer. What changes is how much of the underlying work has already been done before that judgment is required. NDA reviews that used to consume hours now move faster. The time recovered flows into the work that actually required a lawyer to begin with: product launches, partnership agreements, the strategic deals that don’t have obvious answers.
“We didn’t go to law school to sit there trying to organize your own inbox,” Kevin says. “AI tools like Ruli have helped us remove some of those things, or improve them, so that we can be strategic thinkers and thought leaders with our business. And that’s the reason why I hire good lawyers — because you want that expertise focused on the strategic deals, the strategic products and partners.”
The legal team at MasterClass covers the scope of a function twice its size. What changed was not the headcount. It was the cost of getting from a question to an answer, and what it means for a lean legal team when that cost drops far enough that more work — more research, more contracts, more strategic preparation — stays in-house.
“We didn’t go to law school to sit there trying to organize your own inbox. AI tools like Ruli have helped us remove some of those things so that we can be strategic thinkers and thought leaders with our business.”
— Kevin, General Counsel, MasterClass
Customer Stories
