Roberto Cipriani

Hello, I’m Roberto. I help founders lead from within.

I work with founders and executives who want to push beyond their limits and lead from within. My approach draws from years spent building and scaling companies, where I learned firsthand what it takes to lead with clarity and steadiness in moments of pressure.

Roberto Cipriani headshot

Where I’ve Worked

Advisory/Mentoring Roles

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About

Roberto Cipriani is a technology leader, passionate entrepreneur, and innovator who co-founded a startup and grew it from an idea into a category-defining company and industry leader. In 2014, he co-founded Paper Education and, as COO/CTO, led the technology, product, people, finance, and operations teams in building a robust educational support platform that reached more than three million students across North America.

Before his entrepreneurial journey, Roberto pursued graduate studies in Computational Neuroscience at McGill University, following a Bachelor of Science in Physiology. His academic background fostered a deep curiosity for systems thinking, data analysis, and technology—skills that became foundational to his later work in building scalable, mission-driven organizations.

Today, Roberto channels his experience into coaching and advising startup founders and executives. Having led through growth, complexity, and uncertainty, he brings a balanced perspective that combines analytical precision with empathy. His coaching practice helps high-potential leaders navigate inflection points, strengthen leadership presence, and build organizations that endure with clarity and purpose.

Contact

To get in touch, please reach out directly via LinkedIn.