The founder-CEO of LiveSchool, a Nashville-born K-12 behavior platform that started as a paper-paycheck problem and ended up in more than 1,200 schools.
The problem Matt Rubinstein set out to fix in 2011 was banal. It involved paper. His Nashville middle school ran a weekly ritual called the "paycheck," in which students who behaved well collected small paper bills that they would eventually spend on rewards. The students liked the paychecks fine. The teachers, who had to print the paychecks, count the paychecks, distribute the paychecks, chase the paychecks and audit the paychecks, did not. This is the kind of problem that in most schools stays a problem forever because the person best positioned to solve it, the classroom teacher, is also the person with the least amount of time to do anything about it.
Rubinstein, then a KIPP Nashville teaching fellow assigned to 5th grade Guided Reading and 6th grade Math, was less busy than that, or rather he was just as busy but slightly worse at ignoring the paperwork. He was 23, a recent Oberlin philosophy graduate by way of Staples High in Westport, Connecticut, and he had picked up enough programming to build a rough iPad app that let his colleagues award points with a tap. Within weeks the 5th grade team was saving something like two hours a week. He named the thing LiveSchool.
Fifteen years later, Matt Rubinstein is still running it. That sentence contains more information than it looks like it does. Education technology is a category in which founders are notoriously replaced by professional managers around Series B, in which companies pivot from one segment to another every eighteen months, in which brand names get shuffled through private-equity rollups until nobody can remember which product used to be which. LiveSchool has done none of that. Rubinstein has been CEO since day one. The product still does, essentially, what the iPad prototype did: it lets teachers award and track points for behavior, in real time, so that schools can run positive-reinforcement programs without drowning in paper.
The company today serves more than 1,200 K-12 schools in 48 states and at least 10 countries. In the most recent school year LiveSchool users tapped their way to 87 million awarded points and 1.8 million redeemed rewards. Those are the numbers on the About page. The interesting number is the one that isn't there: the count of paper paychecks not printed.
LiveSchool is headquartered at 101 Creekside Crossing in Brentwood, Tennessee, an office park south of Nashville that is not, by any measure, a place people expect K-12 SaaS to come from. Which is the point. The company was founded by someone who was, until the day it was founded, the customer. The customer's boss was a principal, not a venture capitalist. The first product feature request came from a fifth grade team meeting. The Series A - a comparatively small $750,000 round closed in June 2014, part of a $2.45 million total to date - came from a Nashville venture fund. LiveSchool has never had to pretend to be from somewhere else.
Behavior is a symptom, and school culture is the solution. - Matt Rubinstein, Founder & CEO, LiveSchool
LiveSchool's product philosophy leans on a specific number: five positive recognitions for every one correction. That ratio comes out of decades of classroom-behavior research; Rubinstein's contribution is building software that makes it cheap enough to actually maintain across a school day. Every teacher tap on the app pushes toward the higher side of the ratio.
Rubinstein's summary of the theory is deliberately shorter than the theory. "Kids want to be good," he says, "what gets noticed gets repeated." The product does the noticing.
Source: LiveSchool About page and public filings. Bar widths are illustrative, not proportional to national totals.
In 2011, Rubinstein was the KIPP Nashville teacher assigned to help run the school's paper "paycheck" system. Students earned bills for positive behavior and cashed them in for rewards. The kids loved it. The staff were drowning. Rubinstein wrote a rough iPad app that let teachers award points with a tap. The 5th grade team got two hours of their week back. He called it LiveSchool and never stopped working on it.
A SaaS platform that supports PBIS (positive behavior intervention and supports) programs, house-points systems, digital rewards stores, family engagement, and behavior data insights. Bring-your-own-device, web-based, paperless. Sold B2B to K-12 schools, mostly in the U.S. Adjacent to classroom management, but the pitch is culture, not compliance.
Staples High School in Westport, Connecticut, then Oberlin College (BA in Philosophy, 2010). Early jobs: counselor at the Summer Institute for the Gifted (2007), teaching intern at KIPP Infinity (2008), teaching fellow at KIPP Nashville (2010). The KIPP network is the through-line: a national charter school operator known for a strong focus on culture and character.
Since 2022, Rubinstein has hosted The LiveSchool Podcast, a running conversation with principals, behavior specialists and district leaders about motivating students and building school culture. It is, functionally, extremely long-form customer research. It also happens to be published on Apple Podcasts and Spotify.
"Kids want to be good."
"Behavior is a symptom and school culture is the solution."
"What gets noticed gets repeated."
"There had to be a better way." (paraphrased from LiveSchool's own origin retelling)
Rubinstein's undergraduate degree is in philosophy, from Oberlin. He wrote the first LiveSchool prototype anyway. The teacher-turned-founder path is well-worn in EdTech; the philosophy-major-turned-solo-developer path is a little less so.
In 2013 LiveSchool was picked as one of 24 finalists in the Wall Street Journal's Startup of the Year competition, out of more than 500 applicants. During the process Rubinstein sat for questioning by tech-writer-and-mentor Vivek Wadhwa. LiveSchool did not win. It also did not disappear.
The company is headquartered at 101 Creekside Crossing in Brentwood, Tennessee. If you drew a Venn diagram of "K-12 SaaS companies with a thousand customers" and "companies based south of Nashville," it would be a small overlap. LiveSchool is in it.
LiveSchool operates with roughly 16 employees. The ratio of schools to employees - 1,200 to 16 - is the kind of number a bootstrapped SaaS founder would put on a slide with no explanation.
He is the founder and CEO of LiveSchool, a K-12 behavior and school-culture SaaS platform he started in 2011 while teaching in Nashville.
A software platform used by 1,200+ K-12 schools to run positive behavior systems, PBIS programs, rewards stores, and house-points competitions.
Staples High School in Westport, Connecticut, then a BA in Philosophy from Oberlin College (2006-2010).
As a Nashville middle school teacher, Rubinstein built an iPad prototype to replace his school's paper "paycheck" system. It saved the 5th grade team about two hours a week and became a company.
101 Creekside Crossing, Brentwood, Tennessee.