Roberto Cipriani

Roberto Cipriani is Co-Founder, former CTO and COO at Paper, an educational technology platform providing 24/7 virtual tutoring to students across North America. He now serves as a board member and advisor to the company.
Roberto earned a BSc in Physiology and pursued graduate studies in Computational Neuroscience at McGill University, while working as a freelance software developer and running RobertoDev.com Inc.
Roberto led the technology, product, people, and operations teams at Paper, building the platform from scratch and pioneering chat-based tutoring after discovering 75% of students preferred text over video. He stepped down from day-to-day operations in 2024 to focus on coaching and advising startup founders.
Paper raised over $390M from investors including SoftBank Vision Fund II, IVP, and Sapphire Ventures, achieving a $1.5B valuation. The company made strategic acquisitions of MajorClarity, Readlee, and Figure Math in 2022-2023.
Paper reached over 3 million students across 500+ school districts in North America, growing from 100 tutors to 1,000 during the pandemic. The platform democratized access to educational support, making tutoring available to students regardless of socioeconomic background.