Matthew Gross and the art of making room

Matthew Gross took a classroom problem to a bat mitzvah. Two college friends, both veterans of advanced mathematics and statistical analysis, seemed promising people to ask. How many ways could a teacher divide 24 students into six equal groups? They could agree on one thing: the answer was large. A perfectly respectable social occasion had acquired a combinatorics department.

Gross told the story while introducing Grouper, an application for arranging student groups. It was a suitably modest entrance for someone whose previous education company had reached tens of millions of registered users. After Newsela, he had returned to the awkward little decisions that consume a teacher’s day. Who works well together? Who needs help? Which pairing looked sensible on paper and turned into a private comedy club?

His career has moved through a South Bronx music room, subway advertising, state education reform, and venture-backed classroom software. The connecting question is about participation: what has to happen before people can join in? With Newsela, the answer involved rewriting articles. With Grouper, it involves arranging the room.

Before the articles, a music room

Gross graduated from Columbia University in 1994 and joined Teach For America. He taught music at C.S. 50 in the South Bronx. His first professional encounter with education was therefore a room of children and a subject that asks them to listen, practice, and contribute. The later business vocabulary came after the teaching.

He also spent time on a rather different kind of audience. With Columbia friend Joshua Spodek, he co-founded Submedia, which brought animated advertisements to subway tunnels. Backlit still images appeared to move as trains passed them. Passengers found themselves inside something resembling a giant flip book. The system reached Atlanta in 2001 and New York’s PATH tunnels in 2002. Before helping students read the news, Gross had helped commuters watch the walls.

There was a commercial education in that detour: finding an audience, getting an unfamiliar product into established infrastructure, making something work outside a demonstration. Those are recurring problems for founders selling to institutions. A transit authority and a school district have different responsibilities, but neither exists to make a startup’s timetable convenient.

His route back through education included PENCIL, which builds partnerships between businesses and public schools, and the Regents Research Fund. As executive director of the fund, a privately supported affiliate of New York’s education authorities, he worked on reforms connected to Race to the Top. He also helped lead the development of EngageNY, a curriculum resource associated with the adoption of Common Core standards.

By the time Newsela arrived, Gross had seen educational materials from several positions: the teacher expected to use them, the organization helping schools, and the policy operation trying to change practice. A standard can describe what students should learn. Someone still has to find Tuesday’s reading.

Five ways into the same conversation

Gross and fellow educator Dan Cogan-Drew launched Newsela in 2013. The starting proposition was legible in one sentence: news articles, aligned to learning standards, available at five reading levels. A teacher could choose a subject worth discussing without requiring every student to navigate precisely the same prose.

The distinction matters because the topic and the difficulty of the text are separate choices. A student can have something interesting to say about a scientific discovery while needing more accessible sentences to read about it. Newsela’s design gave teachers a way to handle that difference within a shared lesson.

Behind the simple interface sat editorial labor and publishing relationships. By March 2015, the company had 40 news sources, with The Washington Post joining the list. Articles were rewritten at multiple Lexile levels; comprehension questions changed with the difficulty of the reading. Different readers could be asked different questions about the same subject. The apparent simplicity had quite a payroll behind it.

The early business attracted investors as well as teachers. In September 2014, Newsela announced a $4.1 million Series A led by Owl Ventures. Its materials had already been read millions of times by students around the world. The underlying transaction was unusual enough to be interesting: existing journalism acquired a second working life in a classroom.

An ally from the textbook business

One early ally came from the industry Newsela hoped to change. Will Ethridge, formerly chief executive of Pearson’s North American business, invested and became an adviser. Gross met him through Josh Lewis, a Pearson board member. Their relationship put a founder’s classroom ambition alongside an experienced publisher’s knowledge of how schools actually buy.

Gross credited Ethridge with explaining the inner workings of publishing, including large contracts with districts and states. Ethridge also advised on staffing and interviewed senior candidates. A teacher’s enthusiasm could get Newsela into a classroom; building a company required knowing what happened beyond that classroom door.

Gross had another concern as hiring accelerated. In 2019, he described the danger of filling seats too quickly and of repeatedly recruiting people who resembled the existing team. He wanted different thinking. Two successful executive candidates, including chief people officer Eric Bacolas, had challenged him during the process. Disagreement could be evidence of a useful colleague.

That is a revealing preference for the founder of a reading company. A room full of people who can interpret the same evidence differently has more to offer than a room rehearsing the boss’s conclusion. It also makes meetings less soothing, which may be part of their purpose.

When reading becomes a public act

As Newsela grew, its work brought it into the argument over unreliable information. By early 2017, it had 12 million registered users. The company worked with the American Press Institute on teacher resources and offered webinars, including one with PBS NewsHour, as educators looked for ways to address misleading material.

Gross’s answer included an admission that a publishing platform could make mistakes. He argued for helping students validate information and for the company to examine its own work. A tool bringing journalism into schools had a responsibility beyond making sentences easier to read. Students also needed reasons to trust, question, and check what those sentences said.

“The best we can do is police ourselves.”

Matthew Gross, on checking published information, 2017

His own reading habits provided a less corporate glimpse of the same curiosity. As a guest curator in March 2017, he selected stories about climate change and dams, school choice, and the family in the widely shared BBC interview interrupted by children. Education policy and the ordinary disorder of family life could occupy the same reading list.

U.S. history was his favorite school subject. That detail fits comfortably beside Newsela’s interest in connecting classroom topics to the world outside. History, civics, and current events give students material to argue about. A reading assignment can become an invitation to have an opinion, provided the student can get through the assignment.

A bigger company, a different chair

The company’s distribution grew through teachers as well as district agreements. In a 2020 conversation with investor Dave Eichler, Gross discussed the importance of teacher advocacy and a service designed around classroom realities. The product needed to work for the person planning the lesson before it could become a larger institutional purchase.

In February 2021, Newsela announced a $100 million Series D, led by Franklin Templeton and existing investor TCV. It reported annual recurring revenue growth of 81 percent in 2020. The financing supported a broader digital instructional-materials offering. Five versions of an article had become the starting point for a larger business.

In January 2023, Gross handed the CEO position to Pep Carrera, previously CEO of Nearpod. The transition took effect on January 23. Newsela then reported more than 500 employees and 40 million registered teachers and students. Gross became executive chairman, keeping a role in the company he had led for a decade.

Registration figures describe reach, rather than what every student learned. Still, the organizational distance is clear. Gross had gone from helping launch a reading product to running a company with hundreds of colleagues. Changing chairs opened room for a different kind of work.

A second act measured in seconds

In July 2024, he introduced his next venture with a dry assessment: “I’m launching a new edtech application. What lunacy.” Grouper addressed teachers who already had plenty of technology and limited patience for another demand on their time.

His proposed unit of value was “usefulness per second.” Software had to repay the effort of opening it. Grouper’s task was to help educators form groups using their knowledge of students and relevant classroom data. The teacher would supply the judgment; the tool would handle some of the tedious arrangement.

Anton Backer, Grouper’s co-founder and chief technology officer, brought years of experience building Newsela’s technology. Their company philosophy favors fitting existing teaching practices and working with tools schools already use. It also treats artificial intelligence as something to apply where helpful, rather than the starting point for deciding what teachers need.

Gross’s educational connections continued beyond his own products. In September 2024, New Classrooms announced his appointment to its board. He had briefly consulted for the organization before founding Newsela and had followed its work over the intervening decade. The appointment brought him back to another effort to personalize classroom learning.

Newsela and Grouper address different moments in a lesson. One changes the route into the reading. The other helps arrange the people doing the work. Both begin with the teacher’s uncomfortable arithmetic: many students, different needs, one period. Gross has built large ambitions around that small unit of time. The bell remains wonderfully indifferent to a founder’s pitch.