“We put pedagogy before hype. That’s why the most forward-thinking districts are choosing Yourway,” the Yourway Learning CEO, Jerry Weissberg said in a statement announcing the company’s latest funding round.
Yourway Learning just secured $9 million in equity financing, following a $6 million round earlier in the year. The investment is led by Greybull Stewardship, whose managing partner Sasha Kovriga said, “Districts aren’t just checking the AI box, they want results that improve learning and engagement”.
For Weissberg, a former teacher and longtime education entrepreneur, the problem is simple: time. Teachers spend hours each week on lesson planning, grading, compliance paperwork, and parent communication. What remains is too often insufficient for the direct instruction and student connection that drew them into the profession in the first place. The Miami Lakes, Florida-based company, founded in 2017 by Jason Green and Jaime Pales, is positioning its platform as a tool to give some of that time back.
Building an AI System for Classrooms
Yourway Learning offers a suite of AI tools designed to reduce administrative workload and adapt instruction to students’ needs. Its flagship product, Yourway Spark, is a real-time student-facing environment that launched in July and is now in district pilots. Spark aims to do more than generate worksheets or automate grading. According to the company, it can scaffold lessons in real time, surface just-in-time insights for teachers, and personalize activities to align with district standards.
The company emphasizes compliance and teacher control. Students do not need accounts, no personally identifiable data is shared with AI systems, and teachers remain the sole audience for student responses. Spark is designed to meet federal and state-level privacy laws, including FERPA and COPPA.
Weissberg has been vocal about avoiding what he calls “tech for tech’s sake.” In an earlier blog post, he argued that solving the classroom time crisis is the most important lever for improving student outcomes and reducing teacher burnout. That message is resonating in a market where skepticism runs high after decades of overpromised education technology.
Funding and Market Context
The funding will support Spark’s rollout, deeper integration with district technology systems, and expanded professional development for teachers. Yourway is also inviting new districts to join pilots this fall.
The company enters a market with competitors like Carnegie Learning, DreamBox, and Khan Academy, who have all launched AI-powered learning tools, while Microsoft and Google are embedding classroom-facing features into their productivity suites. Market researcher HolonIQ projects that the global AI-in-education market will surpass $30 billion by 2032.
Districts, however, are cautious. Concerns about student privacy, uneven implementation, and the potential for AI to depersonalize teaching remain significant hurdles. Surveys show teachers are divided: some report workload reductions and better student support, while others fear inequities could widen if tools are rolled out inconsistently.
Yourway points to early pilot data showing promise. In state-level trials, 53 percent of participating educators reported that AI reduced workload and supported high-dosage tutoring. Hollin Wakefield, Yourway’s chief product and technology officer and a former classroom teacher, said, “With Spark, we set out to build something fundamentally different from anything else on the market: AI that is aligned to teachers’ preferred classroom activities and that responds to students’ needs in real time”.
The company stresses that Spark is not as a replacement for teacher judgment but a tool for efficiency and differentiation. For instance, teachers can use Spark to generate lesson scaffolds tailored to student levels or create compliance documentation more quickly, freeing them for face-to-face instruction. The next test comes as more districts join pilots this fall. If Yourway can show that its tools save time without sacrificing quality, it may find a receptive audience among school leaders facing tight budgets and mounting teacher attrition.
