Jim Calabrese recalls that when he began to climb the corporate ladder early in his finance career, an executive mentor told him, “Never be afraid to make the coffee.” This curious advice caught Calabrese’s attention, so the up-and-coming executive listened carefully as the mentor added: “As an executive, you need to be able to get dirty—to roll up your sleeves. You don’t want to be the person who can’t do a mundane task because you’re in love with your title.” Today, as a CFO, Calabrese serves up his own bite-size mentoring verbiage in this way: “There’s nothing more valuable when you’re the CFO than understanding how the widgets are made—and being the person who’s willing to take on the challenging projects.” Calabrese tells us that he reached the CFO office by aggressively pursuing projects outside the traditional finance realm while also signing up for long stretches on strategic planning teams, where he guided re-engineering projects in the energy and software sectors. His strategic work—along with his operational “grinding and tinkering”—positioned the CPA/MBA hybrid to thrive as a finance leader, especially in his current role as CFO of Finalsite, a private equity–backed SaaS developer serving the education sector.