The leadership team at InsightSquared has a history of experience in sales, marketing, engineering, and financial planning. They have all worked for various companies in these fields such as Mediafly, Cengage Learning, Houghton Mifflin Harcourt, SailPoint, and Cloudmasons. They have also acquired Olono and Tish Marketing. The team is educated in areas such as English, Public Relations/Journalism, Electronics and Instrumentation, and Financial Mathematics.