Philip Cutler has spent much of his working life trying to change who gets a chance. First there were the students who could afford a tutor and the students who could not. Now there are flag football players with international experience and a much less certain professional future. In each case, he has decided that an opportunity worth having needs someone to build the machinery around it.
It is an unusual route from an education degree to a sports business. Along the way come a summer camp, eight years on a city council, a tutoring company that raised hundreds of millions of dollars, and the loss of the chief executive’s job at that company. The résumé is busy. The question beneath it is remarkably consistent: who pays for the opportunity, and who gets left outside?
Cutler co-founded Paper in Montreal with Roberto Cipriani in 2014. He led it through a period when American school districts were buying online support at a pace few education companies had experienced. He left the CEO role in 2024. In 2026, he became head coach of McGill’s women’s flag football team and launched World Flag Series with Joseph Hopmeyer. The classroom has acquired a sideline.
A teacher notices the bill
Cutler graduated from McGill with a Bachelor of Education in 2013. His early interest in education was quite ordinary. He liked school and liked working with children. His parents had encouraged him to pursue work he enjoyed. There was no elaborate master plan requiring a venture capital round in the third act.
Before Paper, he founded Laurus Educational Services. He also co-founded Laurus Summer Camp with Gabriel D’Amico-Mazza in 2012. Their camp offered children time to develop particular skills alongside summer activities. It was an early attempt to bring learning into hours that adults tend to consider empty space between school days.
Teaching brought the economics of extra help into sharper focus. Private tutoring could support children whose families had the money for it. Other children faced the same schoolwork with fewer resources. Building a business that simply sold more tutoring to parents would preserve that dividing line. Paper’s eventual model made school districts the customers, with students getting access through their schools.
That choice changed the job. A teacher could recognize a child’s difficulty; a company selling to districts had to navigate institutional budgets, purchasing decisions and implementation. The educational ambition was personal. The route to delivering it involved contracts. Fairness, it turns out, has quite a lot of paperwork.
The family name on the ballot
Education was only one part of Cutler’s life in Westmount. His grandmother, May Cutler, had been the city’s mayor. In 2009, he ran for a council seat and lost by 42 votes in a three-way race. Four years later, he tried again. He was 24, returning to the same district with experience working with local families.
That second attempt succeeded. He became Westmount’s youngest elected city councillor and served from 2013 to 2021. He chose not to seek another term in 2021. The work sat alongside the development of Paper, a reminder that his involvement with institutions began well before the company became a familiar name in education technology.
It is tempting to read a family connection as a complete explanation. The narrower, more interesting fact is that he had to return after losing. A recognizable surname did not remove the ballot count. The second campaign belongs in the story because it makes persistence concrete: the district was the same, and the result changed.
A business with an unfashionable customer
Paper began as GradeSlam. Its proposition was round-the-clock online academic help, paid for by school systems. Students could ask questions through chat and receive writing feedback. For a family using a district-provided service, the price at the point of use was zero. For the company, providing that access meant hiring tutors and coordinating their availability.
Investors did not immediately see an appealing business. Cutler has described a Series A process involving 125 funds and at least 300 meetings. Earlier education technology companies had disappointed venture investors, making the sector a difficult place to raise money. A promising conversation had to overcome a history the founders had not personally created.
Three hundred meetings is an awkward number for a founder’s story. It is too many to sound effortless and too specific to hide inside a word like determination. Each meeting represents another occasion to explain the buyer, the service and the scale. The eventual financing can obscure how long the same explanation had to be repeated.
“Tenacity is the only thing that will get you through.”
Philip Cutler, on building with Roberto Cipriani
His account of the partnership with Cipriani gives that persistence a human scale. He has written that there were days when he questioned himself and the business, and that his co-founder helped renew his motivation. The public version of a company usually has a tidy founding date. The private work, even in Cutler’s own telling, is considerably less tidy.
When the school doors closed
The closure of school buildings in 2020 transformed the market for online educational support. Cutler argued that districts would need services like Paper, even while their immediate attention was consumed by the transition. Investors recommended cutting jobs. He asked for a quarter to see whether his reading of the market would hold.
By early June, Paper had secured a large agreement with Atlanta Public Schools. The expected demand arrived. What had been a difficult proposition to finance became a company expanding rapidly across American districts. In February 2022, Sapphire and SoftBank Vision Fund 2 led a US$270 million Series D round.
The money supplied a striking headline. The more useful detail is what it was intended to support: a service available beyond the school day, with districts buying access for their students. McGill reported more than two million students served in June 2022. By February 2023, its account put Paper’s reach at three million students.
Those dates matter. Growth figures describe a period in a company’s life; they do not automatically describe its present. They also count reach rather than prove what each student learned. Paper’s scale established the size of the opportunity. The harder question was how reliably that opportunity could turn into useful help.
The lesson after the growth chart
Paper’s offer depended on students choosing to use it. Cutler spoke about designing around their habits, including a preference for chat over a live video call. A teenager looking for help late at night might not want to appear on camera. The reasoning was practical: a tool can be available and still feel like something a student would rather avoid.
Availability also came under scrutiny. Districts and educators raised questions about engagement and the limits of chat-based tutoring. New Mexico ended its contract in 2023, citing concerns including enrollment and student engagement. Cutler responded that the partnership was still in its early implementation phase and needed time to take hold.
Other reporting examined tutors handling several students simultaneously, complicating expectations of one-to-one support. These were questions about the service families and schools received. A founder’s educational purpose could explain why a company existed; it could not settle the question of whether the company was doing the job well.
In April 2023, Cutler announced a restructuring affecting 81 employees. He described a push toward a broader educational support system and a need for focus. Paper had acquired career-planning company MajorClarity and reading platform Readlee. Expansion of the product and contraction of the workforce were now happening within the same business.
By July 2024, Rich Yang had taken over as interim CEO. The following month brought confirmation of a reduction of roughly 45 percent in headquarters staffing. Cutler’s decade as CEO had ended. That ending belongs beside the funding milestones. Leaving it out would turn a career with consequences into a decorative growth chart.
Back at McGill, this time with a playbook
Cutler’s connections to McGill have continued through different roles. He served on the Faculty of Education’s advisory board and received the 2023 Young Inspiration Award at the Desautels Management Achievement Awards. In May 2026, the university announced another appointment: head coach of its women’s flag football program, entering an eight-team RSEQ league that season.
He brought playing and coaching experience to the position. Cutler founded KGP Elite Flag Football in 2023 and served as both head coach and quarterback. McGill described the team as having reached a top-eight world ranking and competed at the iFlag World Championships. Football was already part of his working life, rather than a hobby newly attached to a business announcement.
The return has a satisfying symmetry without needing to be forced into destiny. The education graduate is again responsible for helping young people develop, this time through a university team. There are plays to teach, athletes to prepare and opponents whose cooperation cannot be assumed. The score provides unusually prompt feedback.
A stage the players can actually stand on
With Hopmeyer, Cutler has taken the sporting interest into professional events. World Flag Series began with a women’s competition in Tampa on July 25, 2026. Its launch plan called for 30 compensated athletes from more than ten countries. The emphasis on compensation gave the word professional a concrete meaning.
The inaugural event was followed by WFS2 in Toronto on September 19. H.E.R. won both championships. Toronto also introduced an expansion franchise, the Midnight Ballers, who finished runners-up. There is now an event history to discuss, with results and teams, rather than only a proposal about what the sport could become.
Tampa19 SEP 2026
TorontoWorld Flag Series’ first two events
Cutler has described the professional experience in terms that extend beyond the game: the broadcast, the stadium and the stories that make fans care about individual athletes. He wants young players to see a future in the sport. A professional stage needs players, but it also needs people who will return to watch them.
School tutoring and women’s flag football have different customers, costs and measures of success. The connection in Cutler’s career is the work of building access around people whose abilities already exist. A student needs usable support. An athlete needs a place to compete and be seen. His next chapter will be judged in those everyday transactions: a session that helps, a team that develops, a spectator who comes back.