How Cimplifi’s Sole Counsel Transformed Contracting with Automation and AI

Cimplifi was stepping into a new era. The company had just rebranded as a full-service legal tech ecosystem. Its 25th anniversary was around the corner. And Marla Crawford joined as the first general counsel.

But just as Crawford was getting the lay of the land, she discovered a roadblock that threatened to stall momentum. “I realized we had contracts all over the place,” she said. “That was not going to work for me.”

Coming from a Big Law background, Crawford knew disorganization wasn’t just inconvenient—it was risky. Without a central system, it was difficult to understand what had been agreed to, how terms were changing, or whether anything had slipped through the cracks.

“I needed a way to quickly find agreements, feel confident about what I was signing, and get answers when I had questions,” said Crawford.

Cimplifi chose the same tool its clients trust: Docusign CLM

Cimplifi’s experts had guided countless clients through Docusign CLM rollouts, so bringing it in-house was an easy sell.

“Docusign CLM has so much functionality that it was easy to develop our workflows and roll out a program that worked for us,” said Crawford.

Agreements move from pre-execution to signature in one trackable flow, helping Crawford spot bottlenecks, measure performance, and prove value to leadership. “Our process is so seamless now,” she said. “It’s been very good for us and for our clients.”

Skepticism gave way to 100% adoption

Many on the sales team clung to their old ways, convinced a new system would never take hold. But Crawford wasn’t deterred.

“I’m more of a stick person than a carrot person,” she said. “If an agreement wasn’t in the system, it wouldn’t get signed.”

Her mix of firm policy, open office hours, and steady support won them over. “Today, we have 100% adoption,” she said.

CLM puts the general counsel in control, without slowing the business

Before, Crawford had to read agreements start to finish whenever changes came in—a painstaking process that slowed everything down.

With CLM, she built workflows that surface only the clauses and edits that truly need her attention. Routine changes go to her contract specialist, while she stays focused on the most critical sections and terms.

Even the skeptics came around once they saw how quickly deals moved.

“I have one place where I can make comments and tell our team what I’d agree to if it’s not exactly what the counterparty suggested,” she said. “The team is thrilled because it saves us a lot of time and helps us get to the goal everyone cares about—the client’s signature—much faster.”

When a high-stakes question came up, Docusign AI helped narrow thousands of agreements to just 16

Cimplifi faced another challenge when a backlog of legacy agreements needed to be audited for a high-stakes business question. A manual review would have taken months and cost a fortune in outside counsel fees.

Crawford turned to Docusign AI to speed the process. “I didn’t have time to read every agreement, and I didn’t want to pay anyone else to do it,” she said.

Her team built AI models—powered by Docusign Iris, the platform’s AI engine—to analyze the entire portfolio and flag the agreements that required a closer look. In minutes, the models narrowed thousands of agreements down to 76. Crawford personally reviewed just 16.

“Docusign Iris saved me thousands of dollars and hours of work, and I got the answer I needed to take the right business action.”

Running a legal department of one leaves no room for inefficiency

With automated workflows and AI surfacing only what needs her expertise, Crawford stays in control without getting buried in busywork.

“I have a great team supporting me, but when it comes to legal terms, that’s my responsibility alone,” she said. “Having Docusign highlight exactly what I need to review gets us to an earlier signature.”