Paper Trails—Roberto Cipriani's Mission to Give Every Student a Fighting Chance

May 21

MAY 21, 2025 | 00:36 | Episode 71

Roberto Cipriani co-founded Paper Education

In 2014, Roberto co-founded Paper Education. As COO/CTO, he led the technology, product, people, and operations teams to bring our vision to life—ensuring every student had access to the help they need to reach their full potential. Our business grew into a robust educational support system powered by a talented team that reached over 3 million students. Now, I’m channeling my experience into coaching and advising startup founders, helping them navigate growth, leadership, and the challenges of scaling a company.

ABOUT THIS EPISODE

Summary

Roberto Cipriani, the founder of Paper, elucidates the transformative journey of his educational technology company, which aims to democratize access to tutoring across North America. Launched initially as Grade Slam in early 2014, the company evolved through a rebranding in 2020, recognizing the inadequacies of its original name. Cipriani's commitment to providing affordable educational support stems from his own academic experiences and the desire to offer the same support he received to those in need. Throughout this podcast, I delve into the intricacies of navigating product-market fit, the significance of understanding customer pain points, and the delicate balance between rapid growth and thoughtful decision-making. The discussion ultimately emphasizes the importance of investing in oneself as a leader to foster a thriving organizational culture and to ensure sustained impact in the education sector.

Story

Grade Slam, initially conceived as a fusion of educational passion and sports enthusiasm by its founders, underwent a transformative journey since its inception in early 2014. The name, emblematic of their vision, proved to be a misnomer, as the company evolved to focus on democratizing access to tutoring, ultimately rebranding as Paper in 2020. This shift not only marked a new identity but coincided with the onset of the COVID-19 pandemic, which catalyzed an unprecedented demand for educational support. Throughout this episode, we delve into the intricacies of Paper's mission and the founders' commitment to ensuring that every student, regardless of socioeconomic status, has access to quality tutoring. The narrative unfolds through the lens of Roberto Cipriani, whose journey from a software developer to a tech entrepreneur illustrates the profound impact of technology in transforming educational landscapes. His insights provide valuable lessons on navigating the challenges of startup growth while staying true to one's mission, underscoring the importance of understanding customer needs before devising solutions.

Takeaways

The journey of Roberto Cipriani showcases the importance of understanding customer pain points before developing solutions.
Roberto's experience reveals that recognizing when to slow down during rapid growth is crucial for making impactful decisions.
Investing in personal growth as a founder creates a multiplier effect on organizational success and culture.
The evolution of Paper from Grade Slam highlights the significance of branding in aligning with the company's mission and values.
Roberto emphasizes the need to reframe budget conversations by demonstrating how solutions can enhance existing financial resources.
The success of Paper is rooted in its mission to democratize education and provide accessible tutoring for all students.