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499

Roberto Cipriani

Logo
Roberto Cipriani
CEO & Co-Founder of
Paper (2014)
About

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.

Before founding

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.

Founder Insights

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.

Experience

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.

Scale & Impact

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.

499

Roberto Cipriani

Paper
Co-Founder
Logo
Roberto Cipriani

Company(s)

Paper

Industry

SaaS

Year Founded

2014

Stage/Funding

Series D • $496M

Company Location

ca

Connect

About

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.

Before founding

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.

Founder Insights

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.

Experience

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.

Scale & Impact

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.

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