David Lipkin Is Building a Report Card for What Students Can Actually Do

David Lipkin remembers the house. Not the one he later built with his wife during a Vermont winter, though that house deserves its own sturdy paragraph. This was the imaginary house of seventh grade: a floor plan, a fixed budget, furniture to choose, and a stack of decisions disguised as schoolwork. Decades later, it remains one of the classroom experiences he can summon in detail. The lesson had walls. The arithmetic had consequences. Imagination had to negotiate with cost.

Most assignments enjoy a shorter afterlife. They are completed, graded, returned, and gradually composted at the bottom of a backpack. A letter or number survives in a database, but the interesting evidence - the revisions, judgment, collaboration, and sudden competence - becomes difficult to see. Lipkin has spent more than a decade trying to rescue that evidence from oblivion.

He is the co-founder and CEO of LiFT Learning, a small education technology company in Bristol, Vermont. Its platform lets schools design real-world projects, connect work to explicit skills, give feedback against those skills, and assemble the results into portfolios that grow with the learner. The practical ambition is to make assessment describe ability rather than merely summarize compliance. It is a large systems problem wearing the modest clothes of a gradebook.

A composer enters the system

Lipkin did not take the standard route into software. He earned a degree in music theory and composition from Towson State University, worked as a teacher, and later served young people and families as a school-based clinician. Those occupations share a useful tension. A composer needs structure, but structure alone produces no music. A clinician needs a framework, but the person in front of the framework remains irreducibly particular. Education has the same quarrel with its systems.

His future co-founder, Josie Jordan, was an English teacher immersed in personalized and competency-based programs. The two married, raised three children, and kept returning to what they had watched happen in their Vermont community: students changed when their interests, goals, and lives outside school were treated as educational material rather than charming extracurricular debris.

In 2014, Lipkin and Jordan co-founded SchoolHack Solutions. The name borrowed from hacker culture, where progress begins with a creative use of whatever tools are already on the bench. They began developing LiFT, initially a platform that connected student interests and academic work in a shared workflow. Entrepreneurship was a new direction for both of them. Their home already contained three young children. The founders responded to the return of sleep by launching a startup.

They nicknamed the company their fourth baby: always hungry, awake at night, and wholly dependent on them. The joke was accurate enough to be slightly menacing. Long hours, financial pressure, crashed websites, hires that disappointed, and promising deals that evaporated all entered the family calendar. Yet the couple arrived with an eccentric kind of preparation. They had taken students to the Amazon rainforest twice. They had built that real house in a frigid winter. They had three children in two years while studying and developing school programs. A software company was at least indoors.

From conviction to workflow

“Student voice” is among education's most agreeable phrases. The trouble begins on Tuesday morning, when teachers need to design a project, connect it to standards, guide twenty-five learners, give useful feedback, track progress, report results, and still locate the charging cable. A philosophy that cannot survive the timetable becomes decoration.

LiFT's product logic is an attempt to make the philosophy operational. A school brings its own competency framework and instructional model. Educators and learners can co-create interdisciplinary projects. Work is tagged to specific skills. Feedback attaches to evidence. Separate demonstrations accumulate into skill portfolios. Reports describe growth through actual work rather than allowing the work to vanish behind an average.

The order matters. Software follows the learning design, not the reverse. Lipkin has argued that schools need more than a technology purchase to change. They need new teacher roles, new assessment habits, patience, support, and a willingness to confront “business as usual.” A shiny dashboard can digitize an old routine with impressive efficiency. The deeper work is changing what the routine values.

By 2016, SchoolHack had moved from a three-school beta to use in twenty Vermont schools, with more joining elsewhere. A $350,000 working-capital loan from the Vermont Economic Development Authority helped the company expand. In 2017, it joined the LearnLaunch Boost accelerator in Boston. The company later took the name of its product, becoming LiFT Learning, a less mischievous label for work that had become more infrastructural.

The portfolio is the point

A conventional grade is wonderfully compact. It also combines too many things: content knowledge, punctuality, effort, test performance, and the teacher's private arithmetic. Portfolios are messier, but their mess is closer to life. A student can point to a prototype, essay, presentation, community project, or revision and explain what changed. The evidence invites a conversation instead of ending one.

Lipkin's writing repeatedly returns to the whole learner. Personalized learning plans should influence daily experience, not sit in an annual folder. Evidence from beyond classroom walls should count. Teachers, not only students, deserve professional learning that is ongoing and connected to goals. There is no single entry point for every school; one may start with competencies, another with engagement, a third with educator development.

That pluralism saves the work from becoming another grand educational formula. LiFT is not asking every school to become identical. It is trying to give different communities enough common machinery to make their chosen version of learner-centered education visible, assessable, and sustainable.

A founder's evidence

The advice Lipkin has offered entrepreneurs is strikingly free of theater. Keep the original inspiration nearby. Know the limits of the founding team. Celebrate wins with abandon. The last instruction sounds frivolous until placed against the long sales cycles and slow institutional change of education. A mission can be important and still be exhausting. Progress needs witnesses.

For Lipkin and Jordan, the original evidence came from young people in their community whose engagement and confidence grew through personalized learning. Remembering those students restored energy when websites broke or deals fell through. It gave the founders something more durable than optimism: a concrete account of change already observed.

LiFT's recent work has moved further into the plumbing. A 2024 partnership with Edlink connected the platform to common learning-management, student-information, and identity systems. In 2025, Lipkin was listed among the domain experts and technical advisors for a LearnerStudio report imagining a more connected technology stack for learner-centered futures. Integration is rarely the part of education technology that earns an inspirational poster. It is, however, the part that decides whether an idea survives contact with a school.

There is a revealing patience in this phase of the company. Consumer software can ask a person to abandon one habit and acquire another before lunch. A school contains students, families, teachers, administrators, schedules, policies, contracts, reporting rules, and a cupboard full of previous reforms. Each new tool enters a crowded room. If it cannot exchange data with the systems already there, the burden lands on educators as duplicate entry, awkward exports, and one more password. The visionary feature is sometimes a clean roster sync.

That reality has kept Lipkin's public argument grounded in implementation. Learner-centered education requires aspiration, but it also requires rubrics people understand, feedback they can deliver, reports families can read, and professional learning that continues after launch day. The platform must hold a school's ambitions without forcing every teacher to become a part-time database administrator. This is slow work because institutions are made of people, and people quite reasonably notice when a promised improvement adds six clicks. LiFT's decade-long evolution suggests a founder willing to remain with the unglamorous middle, where a compelling idea either becomes routine or becomes a conference slide.

The arc from a seventh-grade house to a portable skills portfolio is not perfectly straight, but it has good foundations. Make the work real. Name the capabilities it requires. Leave room for judgment. Preserve evidence of growth. A student should finish a project with more than a score and a memory. They should leave with proof.