Toby Jackson

As the chief technology officer at Mainstay, Toby Jackson leads the charge in product, engineering, and support, pushing boundaries and driving innovation every day. Before taking the helm at Mainstay, Jackson served as the head of Global Digital Delivery at Argo Group, where he oversaw the digital organization, enterprise architecture and integrations, and global group data units. But his impact stretches far beyond these accomplishments. Jackson’s work has spanned a number of industries including sports entertainment, health care, investment finance, commercial insurance, and educational technology.
From developing high-performance socket servers to building portfolio management systems to driving automation with artificial intelligence, Jackson has always been at the forefront of technology. His ability to balance innovation, scalability, delivery, and performance while juggling multiple roles is a testament to his dedication and work ethic. But what truly sets Jackson apart is his unwavering positive attitude and desire to learn. He believes that with the right mindset and a willingness to learn, anything is possible.