Matthew Kennard Is Counting What Happens After the Workshop

The cardboard had become a small mountain. It sat in distribution centers run by TJX, parent of TJ Maxx and Marshalls, where Matthew Kennard worked in strategic finance. Cardboard is not the sort of asset that gets a young financier invited to ring a bell. It is dull, bulky and usually discussed only when somebody wants it gone. Kennard and his colleagues discovered it could be sold back into recycling. They built a recovery cycle around the waste and found a meaningful improvement in margin.

The story has become Kennard's favorite proof that finance is most useful when it leaves the finance department. A spreadsheet could quantify the pile. An operator had to walk into the building, ask why it was there and talk with the people who knew the machinery. Two decades into a career that began in banking and now places him in the chief executive's chair at BetterLesson, he still argues for the walk.

This makes him an unusual figure in education technology. He was not a classroom teacher who learned business. He was a business operator who learned classrooms, slowly and at close range. The sequence matters. It helps explain why he is suspicious of bright features without a measurable result, and why his language lands somewhere between an earnings review and a faculty-room conversation.

01 · The useful outsider

Finance gets him through the door

Kennard studied history and political science at Yale, then accounting and entrepreneurship at the University of Chicago Booth School of Business. Between those schools and after them came Banc of America Securities, technology investing at Investcorp, TJX, Rackspace and iHeartMedia. His assignments covered leveraged finance, growth investments, planning, capital strategy and corporate development. He learned to read a business in different dialects.

At LearnZillion, a K-12 digital curriculum company, the dialect changed again. Kennard arrived to lead finance and corporate operations, then became CFO and head of operations. Co-founders Eric Westendorf and Alix Guerrier let him range beyond the ledger. He ran customer experience, spoke with hundreds of users and went into classrooms to watch the product encounter reality.

He asked questions with the cheerful persistence of someone who considers ignorance a temporary condition. His advice to aspiring finance leaders is to master the expected work, then spend the extra hours learning product, customers and operations. Curiosity, in his telling, is not a charming accessory. It is part of the job description.

“Ask questions until the cows come home.”Matthew Kennard

The classrooms corrected an assumption common among outsiders: that modern content and a device might solve the central problem. What Kennard saw was the force of a skilled educator. Content mattered. Craft animated it. A strong teacher could sometimes overcome weak material; superb material did not reliably rescue weak execution.

That recognition was personal, too. Kennard has called his six years at Roxbury Latin, the small Boston boys' school, his most transformative education, ahead of Yale or Booth. What endured was not a platform. It was the human texture: exacting instructors, a close class of 42 and an ethic of public service. Technology could expand access and sharpen decisions. It could not manufacture that inheritance by itself.

02 · The overlooked engine

A workshop is an event. Learning is an arc.

BetterLesson began in 2008 as a place for teachers to share lesson plans. By the time Kennard became CEO in February 2021, it had grown into a professional-learning company offering coaching, workshops, learning walks and self-directed tools. The appointment paired an operator with a company founded by educators. Co-founders Erin Osborn and Alex Grodd could focus on partnerships and product while Kennard took responsibility for scale.

He arrived with a contrarian thesis hiding inside an unglamorous category. Professional learning, he said, had been treated like edtech's dusty backwater. Yet it might be the part that determines whether everything else works. Districts can buy rigorous curriculum and capable software, but neither implements itself. Teachers, principals and instructional coaches have to turn them into practice, day after day, among actual students.

Kennard is fussy about the noun. He prefers professional learning to professional development because development too easily evokes the one-off spectacle: a lively day, a handsome binder, and little evidence of what happened afterward. Learning implies duration. In BetterLesson's model, a district begins with an outcome, gives educators a mix of coaching and group work, watches practice, measures progress and adjusts.

The distinction is also a rebuke to software's favorite proxies. Logins, minutes and feature adoption are convenient to display. They do not tell a superintendent whether students are reading more capably or whether a teacher feels better equipped to teach them. Kennard wants vendors to accept some responsibility for that gap. Usage can describe activity. It cannot, on its own, claim impact.

03 · The deal and the day after

How an ending becomes distribution

Kennard helped lead the sale of LearnZillion to Weld North Education in December 2019. He remembers sitting in a San Francisco hotel for the closing call, available to chase the last signatures. The final ritual was almost comically administrative: check the documents, confirm the money, release the escrow. Then he went to sleep.

The next morning carried an ache. A company can be sold for good strategic reasons and still feel like something has died. Teams change. People leave. The hard days that once seemed permanent turn out to have been finite. Kennard's lesson was not sentimental resistance to deals. It was the opposite: if the work truly helps children, the goal is broader distribution, even when another owner can carry it farther.

That belief resurfaced from the buyer's side in February 2025, when BetterLesson acquired Abl. Abl brought scheduling, academic-pathway design and resource-allocation tools used by districts across the country. BetterLesson brought professional learning and instructional support. Together, the pieces suggested a larger ambition: connect what a district plans, what it funds, how it supports adults and what students can access.

“Education remains a human interaction.”Matthew Kennard

04 · More machine, more humanity

AI earns its place by returning time

Kennard's position on artificial intelligence is neither alarmist nor devotional. He sees three practical lanes: make district administration less burdensome, help teachers plan for varied student needs, and teach students responsible use. An observation tool might analyze teacher talk, student talk, wait time or academic language. The machine can shorten the journey from evidence to insight. A person still decides what the insight means and what to do on Monday.

At his mother's kitchen table, he once offered a compact demonstration. Both of his parents are lawyers. When his mother doubted whether a language model could write an adequate explanation of a tiresome regulatory task, he asked Claude to try. It produced a useful paragraph in seconds. His conclusion was pragmatic: refine it, verify it and save the hour for work that requires a lawyer's judgment.

The same boundary applies in school. Technology should remove analysis that consumes time without displacing the relationship that gives teaching meaning. Kennard is fond of reminding audiences that education has already absorbed computers, the internet and one-to-one devices. The responsible question is not whether a tool feels novel. It is which human purpose the tool serves.

05 · The other first day

Belonging begins at the first tee

Kennard's work outside BetterLesson makes the systems argument more sociable. In 2023 he co-founded No Bunkers No Bogeys Golf Club with Jonathan Jenkins, a clinical and sport psychologist and a friend from middle school. The project was designed for golfers who have felt unseen or unwelcome in the game's culture. Its matching idea emphasizes personality, pace and playing style, not merely handicap.

The venture is not education technology, but it rhymes with Kennard's day job. Both ask what keeps people at the margin and how a system might be rearranged so they can participate. At BetterLesson, the levers are schedules, coaching, curriculum and district budgets. In golf, they are pairings, meetups and the anxiety of arriving alone at the first tee. The spreadsheet is different. The operating instinct is the same.

Kennard has said he does some of his best reflection on airplanes, in the temporary quiet between meetings, school visits and investor conversations. It is an apt setting for a leader who has spent his career between categories: financier and educator, seller and buyer, analyst and chief executive. His strongest idea is not that numbers should rule human institutions. It is that numbers should make those institutions answerable to the humans they claim to serve.

The pile of cardboard was worth noticing because it concealed value. Professional learning is worth noticing for the same reason. The difference is what is recovered. In one case, margin. In the other, time, skill, confidence and the possibility that a student experiences a better lesson tomorrow than today. Kennard still wants the calculation. He has simply learned where to look for the answer.