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Global Market Insights

SQ Stock Today: February 27 – Jumps Over 20% on AI-Driven Cuts

February 27, 2026
6 min read
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Block stock rallied more than 20% today after Jack Dorsey said the company will reduce headcount from about 10,000 to below 6,000 and lean on AI to streamline operations. Block (SQ) also cited strong year-end demand across Square and Cash App. Investors in Singapore are weighing a leaner cost base, potential margin gains, and execution risks into 2026. Below, we break down what changed, where savings could show up, and how to position around this move.

What moved shares today

Management aims to trim staff from roughly 10,000 to under 6,000 by using AI to automate support, risk, and back-office tasks. The sharp reduction is designed to simplify product focus and speed decision making. The move was first flagged by Jack Dorsey and covered by global media source and the Financial Times source.

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Management highlighted firm year-end activity across Square’s seller ecosystem and Cash App. A healthier gross profit mix, with more services layered on payments, supported sentiment. Investors now expect operating leverage as costs fall, while product monetisation in SMB tools, lending, and card issuance offers incremental upside if engagement stays strong.

The jump reflects a reset in earnings power if AI cost cutting flows through to operating margin. Near term, investors will watch operating expense trends, gross profit per active, and loss rates in Cash App’s financial services. Expect elevated volatility into the next updates on headcount progress, AI deployment speed, and productivity metrics.

Why AI cost cutting could lift margins

Savings should concentrate in customer support, compliance ops, fraud review, and routine engineering workflows. On the revenue side, AI can improve seller onboarding, risk scoring, and ad targeting in Cash App. If Block sustains service quality while trimming layers, we see scope for higher contribution margin across Square hardware, software subscriptions, and Cash App financial services.

Automation can raise model risk, so monitoring false positives in fraud, uptime, and customer satisfaction is key. Compliance needs human oversight across KYC and AML. We will track service response time, dispute resolution rates, and fraud losses. Any spike could offset savings and weigh on take rates or growth, delaying margin goals.

Clear milestones include operating expenses as a percent of gross profit, opex per transaction, and gross profit growth outpacing headcount. Progress updates on staff reduction toward below 6,000 and productivity per employee will matter. If AI improves risk and support costs while keeping churn low, sustained operating leverage becomes more credible into 2026.

Financial snapshot and valuation

Block ended FY2024 with a current ratio of 2.18 and debt-to-equity of 0.07, indicating solid liquidity and modest leverage. Cash per share was 21.53. Net debt to EBITDA was negative, signaling net cash. This gives management room to invest in AI tooling while absorbing transition costs from the restructuring.

Gross margin stood near 41%. Free cash flow per share reached 3.00, with free cash flow growth of about 32% in FY2024. Operating cash flow grew roughly 16%. These trends support the bull case that a leaner cost base can convert revenue growth into stronger free cash generation over the next several quarters.

Price-to-sales was about 2.16 and enterprise value to sales near 1.88 on recent TTM figures. If operating margin rises as costs fall, those multiples could re-rate. We will watch gross profit growth versus opex, and stock-based compensation mix, to judge durability. Analyst signals remain constructive, with a Buy-leaning consensus in recent checks.

What it means for Singapore investors

This is a U.S. growth-fintech exposure. For SGD-based investors, consider position sizing within a diversified global sleeve. A simple plan is a S$10,000 allocation split across two or three tranches to manage timing risk. Hedge USD exposure if currency swings matter for your goals, or keep unhedged for potential USD diversification.

After a 20% surge, dollar-cost averaging can smooth entries. Watch quarterly updates for opex trajectory, headcount progress, gross profit per active, and loss rates in Cash App products. Guidance on 2026 efficiency targets will be key. Any signs of customer support strain or higher fraud costs would challenge the margin story.

Key risks include execution on AI rollouts, regulatory shifts in payments and crypto features, macro sensitivity of SMB sellers, competition, and USD/SGD volatility. A slower consumer, elevated charge-offs, or service quality dips could reduce gains. Maintain a stop-loss policy and revisit thesis if operating leverage stalls for two straight quarters.

Final Thoughts

Block stock surged as investors priced in a smaller workforce, AI-driven productivity, and stronger operating leverage through 2026. The balance sheet looks sound, free cash flow improved in FY2024, and valuation multiples leave room for expansion if margins rise. For Singapore portfolios, scale in with tranches, monitor opex-to-gross-profit, fraud losses, and customer support metrics, and decide whether to hedge USD exposure. The core thesis is efficiency plus steady gross profit growth across Square and Cash App. If both hold, upside remains. If service quality or compliance weakens, reassess quickly. This content is informational only and not investment advice.

FAQs

Why did Block stock jump over 20% today?

Shares jumped after Jack Dorsey outlined deep headcount cuts from about 10,000 to under 6,000 and highlighted AI cost cutting alongside strong year-end demand. Investors expect a leaner cost base to lift operating margins across Square and Cash App if service quality holds and fraud losses stay contained.

How do Jack Dorsey layoffs tie into AI cost cutting?

Management plans to automate support, risk checks, and other back-office workflows with AI. The layoffs reduce layers and concentrate spend on high-impact areas. If automation maintains uptime and customer satisfaction, operating expenses as a share of gross profit should fall, supporting margin expansion into 2026.

What should Singapore investors watch beyond the SQ stock price?

Look at operating expense trends, gross profit per active user, Cash App loss rates, and progress toward a workforce below 6,000. Also track service response times and dispute metrics. These indicators show whether AI savings are real without hurting growth or customer experience.

Is SQ expensive after the spike?

On recent TTM data, price-to-sales near 2.16 and EV/sales around 1.88 are not stretched if margins improve. The upside case needs disciplined opex and steady gross profit growth. Consider dollar-cost averaging rather than chasing a single print after a 20% move.

What are the main risks to the AI cost cutting plan?

Execution risk is highest. Model errors can raise fraud losses or hurt customer support, forcing higher costs again. Regulatory oversight of payments and financial services can tighten. Competitive pressure and USD/SGD swings also matter for Singapore investors allocating capital in USD.

Disclaimer:

The content shared by Meyka AI PTY LTD is solely for research and informational purposes.  Meyka is not a financial advisory service, and the information provided should not be considered investment or trading advice.
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