Matt MacInnis approaches business with the precision of a surgeon, focusing his efforts on the most critical challenges at hand. At Rippling, where he serves as Chief Operating Officer, his leadership style is defined by relentless attention to detail and a refusal to let momentum stall. Rather than spreading himself thin across various functions, he zeroes in on high-impact issues, ensuring that no project loses velocity or precision. This method has played a key role in Rippling’s transformation from a 70-person startup to an enterprise valued at $13.4 billion. Under his operational oversight, the company has expanded its reach as an all-in-one HR, IT, and finance platform, solidifying its position as a leader in workplace management solutions.
Born and raised in Canada, MacInnis pursued his education at Harvard University, where he earned a bachelor’s degree in electrical and computer engineering. Early in his career, he spent seven years at Apple, working in education and business development before realizing his long-held ambition of founding his own company. That dream took shape in Inkling, a digital publishing platform that raised over $102 million in funding and partnered with major textbook publishers. After nearly a decade at the helm, he sold the company and took a step back, exploring the mountains of Big Sur before joining Rippling. Now, as COO, he is responsible for scaling operations and ensuring the company continues to grow without succumbing to organizational inefficiencies.
MacInnis believes that fighting entropy is the primary responsibility of leadership—without deliberate action, everything slows down or loses focus. His approach to executive decision-making prioritizes speed, clarity, and execution, ensuring that no part of the organization drifts off course. He advocates for leaders to be intensely involved where they are needed most, treating challenges with surgical precision rather than relying on broad, passive oversight. This philosophy has guided Rippling through rapid expansion and positioned it for sustained success, proving that in a fast-moving company, controlled urgency is key to keeping innovation alive.