The camera was supposed to be part of the solution. Roberto Cipriani and his co-founder, Philip Cutler, were bringing tutoring online, and video seemed an obvious way to put a teacher and a student together. Then the students started declining the invitation. In Cipriani's recollection, three-quarters of sessions involved a student refusing camera access and simply chatting with the tutor. The software had made an offer. The children had proposed an amendment.
For a developer, there is a particular indignity in building a feature that people would rather switch off. There is also useful information. Cipriani and Cutler listened. The service became a place where a student could ask for help through messages, without first agreeing to appear on screen. Getting the interface right meant accepting that the person using it had a better answer than the people who made it.
That episode offers a way into Cipriani's career. He has spent years working around the distance between what people are offered and what they actually need. At Paper, the company he co-founded in Montreal in 2014, the problem was academic support. Today, as an executive coach, he works with founders and executives on the decisions and habits that shape their organizations. Both jobs require a willingness to hear an inconvenient answer.
A family lesson, followed by a detour
Cipriani grew up in Montreal, the son of Italian immigrants who came to Canada seeking opportunity. Education mattered in his family. His parents' experience of learning a language and finding their place in another culture gave that conviction weight. School represented a chance to move forward, and he understood the opportunities available to him as something to take seriously.
He completed a Bachelor of Science at McGill in 2008 and went on to graduate study. During his academic years, an interest in computer science and data analysis began drawing him toward technology. Eventually he left his studies to pursue that interest professionally. The family commitment to education remained; the route through it had acquired a bend.
There is a neat irony here. A person who would spend years widening access to academic help first had to decide where his own academic path should end. Qualifications can open doors, but they do not choose which room to enter. Cipriani's move into software put him in a different kind of apprenticeship, working on practical problems for businesses that needed something built.
As a freelance developer, he served small and medium-sized businesses, mainly in Montreal. A mutual friend introduced him to Cutler, who ran an in-home tutoring operation and needed technology to help it grow. Their relationship began with work: a client, a developer, and a business with things to organize. The partnership came before the larger ambition.
Who gets help after the bell?
Cutler brought classroom experience to the partnership. He had seen how access to private tutoring depended on a family's means. Cipriani brought the technical skills to explore another delivery model. Together they founded GradeSlam, the company that would later become Paper. The name combined their interests in education and sport. Its eventual retirement suggests that even a founder's enthusiasm sometimes needs an editor.
The underlying problem survived the change of name. An online tutoring business could still reproduce the economics of an offline one: a family paying for each session, an appointment to schedule, and a cost attached to asking for more help. Moving the interaction onto a computer did little for a student whose family could not afford it.
Paper's school-district model changed who paid. Districts contracted for access, making the service available to their students without a separate family bill. By the 2022 funding round, its offering included unlimited, around-the-clock chat support and annual pricing based on student numbers. Tutors were meant to guide students through questions, encouraging understanding rather than supplying the answer.
The distinction matters because an offer of help contains several hurdles. A student has to know it exists, feel comfortable asking, and be able to use it at the moment a problem arises. Remove a price tag and one hurdle disappears. Remove an unwanted camera and another may disappear. The practical work lies in noticing each obstacle separately.
A business that outgrew its name
In 2020, GradeSlam became Paper. That year it announced a C$10 million financing led by Reach Capital, with Bullpen Capital supporting the round. Earlier financing had included C$1.6 million in 2016. Those amounts give the early years some proportion: there was a company being financed and developed long before the much larger numbers arrived.
The rebrand also supplied a calmer name for a service concerned with more than grades. Paper could hold an essay, a question, or the start of a plan. A company name cannot repair a business model, of course. It can stop making the business introduce itself with a sports pun, which is a modest but respectable contribution.
By March 2022, Paper was serving more than two million students across 30 states. Its US$270 million Series D followed a very different milestone eight years earlier: reaching the finals of McGill's Dobson Cup entrepreneurship competition. The distance between a university competition and a financing of that size is considerable. It also measures how much the founders' jobs had changed.
Cipriani became both chief technology officer and chief operating officer. His responsibilities included technology, product, people, finance, and operations. Building software had expanded into building the organization around it. More students meant more than a larger number on a presentation slide; it meant a service and a workforce that had to function at that scale.
The essay that did not need an audience
Chat tutoring produced another small lesson in how people wanted to work. Students submitting essays did not necessarily want to remain online while a tutor read them. They wanted to leave the writing and collect feedback later. That request helped produce Review Center, an asynchronous essay review service alongside live help.
Once again, the useful change concerned the circumstances of asking. A writer could hand over a draft and carry on. Students also began submitting college essays, cover letters, and resumes, extending the uses of the service. The product followed questions that reached beyond the next classroom assignment.
Paper's leadership later explored a broader set of offerings, including educational activities and college and career support. Cipriani described the challenge as expanding without overwhelming the existing product teams. Growth presented a question of attention as much as money: which additional problem deserved the people and time needed to solve it?
For someone carrying both technical and operational responsibility, that question has sharp edges. Every new service joins a queue of commitments. A good idea can still arrive at the wrong moment, or require more work than its advocates imagine. The essay-review episode offers an appealing standard: an identifiable need, expressed by people already using the product.
September 2024, and a different seat
The company also went through a difficult period. In 2024, Rich Yang replaced Cutler as CEO, and Paper cut 45 percent of its headquarters staff before cutting its Canadian tutor workforce. Cipriani stepped away from his day-to-day CTO and COO responsibilities in September, saying he would continue as a board member and advisor.
Paper had faced criticism over tutors supporting multiple students simultaneously while its service was advertised as one-on-one. That dispute belongs alongside the company's ambitions. A promise of access has to meet the experience of receiving help. Funding and reach describe part of the story; the quality of each interaction supplies another part.
Cipriani acknowledged the challenging months and expressed confidence in the company's next phase. A founder's departure from daily management changes the meaning of responsibility. Advice, oversight, and support remain possible, while the running of the business moves to other hands. It is a consequential change after a decade spent helping build the machinery.
The next person to help is the founder
Cipriani now describes his work as executive coaching for founders and leaders. His advisory connections include Alloprof, and he mentors at Creative Destruction Lab Montreal. CDL lists him as an associate in its artificial intelligence stream and as Paper's founder and board director. The technical background remains part of his professional life, alongside the experience of operating a growing organization.
His present concerns are visible in his public writing. After contributing to an Invest Ottawa startup leadership bootcamp, he emphasized hiring, positioning, intentional fundraising, and defining a real outcome. He described capable operators moving quickly without identifying their main constraint, or delaying the hard decision that would bring focus. Busyness, in this account, can become an expensive form of hesitation.
“A company mirrors its leader.”
Roberto Cipriani, reflecting on startup leadership
The observation is plain enough to be uncomfortable. A founder's scattered attention creates work for everyone else. Clarity has consequences too: people can organize around an outcome when the person leading them commits to it. Cipriani's coaching takes that relationship seriously, placing the leader's own development among the practical demands of building a company.
In his May 2025 podcast conversation with Jothy Rosenberg, Cipriani recalled feeling supported as a student and wanting others to have that experience. He also talked about investing in oneself as a leader. Those concerns bring his career's two chapters close together. Help works best when it reaches someone who can use it, in a form they are willing to accept.
The tutoring camera offers a useful final image. A developer builds a way to communicate. The student chooses another way. Something improves when the builder pays attention. Years later, working with founders, Cipriani is still concerned with what happens when a person gets stuck - and with the decisions that make it possible to move.