Ten years ago, when Adobe management finally made up its mind to enter the software-as-a-service (SaaS) realm and become part of the mass migration from selling boxed software to selling its software offerings via subscription, Adobe’s migratory undertaking might well have been compared to that of the arctic tern. With by far the longest such treks known in the animal kingdom, the arctic tern has one of the most widely followed migrations on the planet—and such would be the case for Adobe, whose most dedicated observers were unquestionably its investors. “How do we tell investors that this is a great thing for them, that the metrics on which they’re most reliant actually won’t have any validity for 2 or 3 years, and that they should look at other numbers instead?,” asks Justin Judd, who at the time—as a vice president in Adobe’s corporate legal group—became involved in the massive migration as the company’s finance and legal worlds converged to better address the transformation’s communication challenges. To Judd, Adobe’s migration to SaaS was an inflection point not only for the company but also for his career, which—considering the legal complexities of the migration—would benefit from having direct involvement with Adobe’s executive team and board. What’s more, Judd found himself increasingly intertwined with the company’s finance teams and leaders. “In communicating and developing the strategy and running through this process, I learned the value that finance can have in framing hard decisions for companies and the importance of business context because Adobe invested deeply in understanding what our customers needed,” explains Judd, who—although initially summoned for his legal guidance—seems to have savored the broader communications challenge that was being addressed by Adobe’s finance teams. “’Here’s how our product offerings work. Here are the implications of decisions that we make.’ Let me bring this information back and present it in a way that can be influential and powerful in helping our decision-making to be successful,” remarks Judd, who would trade in his legal moniker in 2018 when he was named CFO of Adobe’s digital experience business—perhaps a less-than-surprise outcome in light of his previous multiyear entrenchment within the company’s finance leadership. However, unlike with the arctic tern, for Judd there would be no turning back. –Jack Sweeney