Stride vs. Chegg: Which EdTech Stock has the Better Upside Now?

By Sraddha Singha | February 26, 2026, 10:33 AM

Amid a favorable demand environment for digital learning solutions, AI-based alternatives and career-focused learning, the United States education market is witnessing growth from the recently announced initiative by the U.S. Department of Education. Education providers like Stride, Inc. LRN and Chegg, Inc. CHGG are also riding the same wave.

The formation of the Accreditation, Innovation and Modernization (AIM) program primarily aims to reform the higher education accreditation system. The expansion of the accreditation reforms is expected to boost recognition for innovative education models and career-focused learning, thus directly or indirectly supporting the prospects of the companies mentioned above.

Stride’s operations primarily focus on the United States market, offering K-12 virtual schooling and career-learning programs. Conversely, Chegg mainly focuses on homework help, textbook services and tutoring services through innovative digital models.

Let’s dive deep and closely compare the fundamentals of the two edtech stocks to determine which one is a better investment now.

The Case for Stride Stock

The sustained secular shift toward virtual and alternative education models is fueling Stride’s prospects in the education market. Parents' dissatisfaction with traditional K-12 education remains high, thus supporting the company’s core value proposition and underpinning management’s confidence in long-term growth.

LRN’s success in aligning its service offerings with the workforce-oriented education trends is substantiated by the recent numbers. During the first six months of fiscal 2026, the Career Learning segment’s enrollments grew year over year by 18.1% to 111,100 students, with revenues growing 20.5% to $547.6 million. Besides, after being threatened by the technical glitches at the beginning of its fiscal 2026, as of now, the volatility has subsided with withdrawal rates being stabilized. This justifies Stride’s consistent focus on its retention initiatives and academic quality investments, which are beginning to show results.

Notably, the company’s operating leverage and disciplined cost management are taking the limelight. During the first six months of fiscal 2026, its adjusted operating income and adjusted EBITDA grew year over year by 23.8% and 21.3%, respectively. Despite temporary headwinds from platform implementation challenges, Stride reaffirmed its full-year revenue guidance and raised its adjusted operating income outlook, signaling confidence in execution for the remainder of fiscal 2026. For fiscal 2026, LRN now expects adjusted operating income to be in the range of $485-$505 million, up from the previously expected range of $475-$500 million.

However, Stride is susceptible to various risks, with the recent technical failure exposing it to execution risk and dependence on third-party vendors. While issues have improved, further disruptions could hurt enrollment retention and reputation. Also, LRN’s margins are expected to face pressure from continued platform investments and implementation costs.

The Case for Chegg Stock

Currently, Chegg seems to be repositioning itself around the $40 billion global workforce skilling market. After years of traffic pressure in its legacy academic business, management has split operations into two focused units, including Chegg Skilling as the growth engine and Academic Services as a cash-flow generator. Early signals regarding this strategic pivot are convincing, with Chegg Skilling revenues increasing 11% year over year in the fourth quarter of 2025 to $17.7 million. Notably, CHGG has integrated AI-powered learner support, predictive nudges, speech recognition tools and conversational AI features across its skilling and language-learning platforms (including Busuu). These capabilities enhance engagement, retention and completion rates, a key differentiator in the competitive edtech landscape.

Another positive factor is the expansion into B2B and enterprise distribution channels. Partnerships with organizations such as DHL, Gi Group, and Woolf University strengthen institutional credibility and broaden distribution. The Woolf partnership is particularly strategic, as it enables skills programs to connect with accredited degree pathways, aligning Chegg’s offerings with credential-based outcomes, an increasingly important factor in workforce mobility.

However, despite all the tailwinds supporting its growth, Chegg’s most significant challenge remains pressure from the legacy Academic Services business. It is experiencing declining revenue and subscriber trends, due to generative AI competition and changing student behavior. Management explicitly acknowledges the disruptive impact of AI on traditional homework-help models, which has weighed on traffic and engagement. Although Chegg Skilling is growing, it remains relatively small compared to the shrinking legacy segment. The turnaround depends heavily on successful execution and sustained double-digit growth in a highly competitive environment.

Moreover, the ongoing restructuring moves are weighing heavily on the cash flow, which was negative $12.6 million as of 2025-end against $50.3 million at 2024-end. The drag was caused by severance expenses tied to multiple restructuring initiatives, with additional cash outflows expected in early 2026. Although these actions aim to improve long-term efficiency, they reflect ongoing operational strain.

Stock Performance & Valuation

As witnessed from the chart below, during the past three months, Stride’s share price performance has outperformed Chegg’s, with the latter indicating a declining trend.