DBX vs BOX: Dropbox vs Box Stock Comparison: AI Score, Valuation, Performance and Upside
Dropbox is a consumer-to-SMB cloud storage business with strong free cash flow and an AI pivot strategy, while Box is an enterprise content management platform with compliance and security as its core differentiation. Dropbox is the better cash flow business today; Box has a more defensible enterprise security moat but slower growth.
DBX vs BOX is SMB cloud storage cash flow machine versus enterprise compliance content management — Dropbox wins if AI document workflows can sustain ARPU growth against Microsoft; Box wins if enterprise compliance requirements create lasting platform lock-in.
DBX holds the edge across 4 of 5 key metrics in this comparison. DBX leads on both 1-year return (+23.42%) and forward P/E quality (10.88x vs 19.07x for BOX), a relatively favorable combination of momentum and valuation. On fundamentals, BOX is growing revenue faster (13.60%), while DBX maintains the higher operating margin (26.10%) — a classic growth-versus-profitability split. Analyst consensus implies meaningfully more upside for BOX (+7.20%) than for DBX (-14.10%).
- value Dropbox's superior free cash flow generation relative to its market cap
- believe AI document workflows through DocSend and Dropbox AI can sustain ARPU growth
- prefer consumer-to-SMB cloud storage with a simpler business model vs enterprise complexity
- want capital return through buybacks funded by Dropbox's strong FCF
- prefer enterprise content management with compliance and security as defensible differentiators
- believe Box AI workflows and suites pricing will accelerate enterprise contract expansion
- value Box's regulated industry focus where Microsoft cannot simply bundle its way to dominance
- are comfortable with lower near-term FCF in exchange for enterprise platform lock-in potential
| Metric | DBX | BOX |
|---|---|---|
| AI score | 33.2 | 29.5 |
| AI rank | #1938 | #2284 |
| Latest close | $35.70 | $34.98 |
| 1M return | +7.11% | +7.90% |
| 6M return | +43.72% | +46.36% |
| 1Y return | +23.42% | +6.55% |
How much would $10,000 be worth today if invested at the start of each period, with all dividends reinvested?
| Period | DBX | BOX |
|---|---|---|
| 1Y ago | $12.34K (+23.4%) started 2025-08-28 | $10.65K (+6.5%) started 2025-08-28 |
| 5Y ago | $11.43K (+14.3%) started 2021-08-30 | $13.66K (+36.6%) started 2021-08-30 |
| 10Y ago | $12.54K (+25.4%) started 2018-03-23 | $26.32K (+163.2%) started 2016-08-29 |
Hypothetical — past performance does not guarantee future results.
| Metric | DBX | BOX |
|---|---|---|
| Market cap | $7.76B | $4.8B |
| Trailing P/E | 19.72 | 51.44 |
| Forward P/E | 10.88 | 19.07 |
| Price/Sales | 3.07 | 7.10 |
| EV/Revenue | 4.21 | 8.02 |
| Analyst target | $30.67 | $37.50 |
| Target upside | -14.10% | +7.20% |
| Metric | DBX | BOX |
|---|---|---|
| Revenue growth | 0.90% | 13.60% |
| Earnings growth | -6.70% | N/A |
| EPS growth | -6.70% | N/A |
| FCF margin | +30.93% | +22.52% |
| Operating margin | 26.10% | -22.15% |
| Profit margin | 17.49% | -19.76% |
| ROIC proxy | N/A | -575.83% |
| Return on equity | N/A | -575.83% |
| Dividend yield | 0.00% | 0.00% |
| Beta | 0.64 | 1.41 |
| Debt/equity | N/A | 2048.84 |
| Current ratio | 1.07 | 0.76 |
| Quick ratio | 1.01 | 0.66 |
Lower drawdown and smaller single-period drops generally indicate a smoother ride, though they do not guarantee lower future risk.
| Period | Metric | DBX | BOX |
|---|---|---|---|
| 1Y | Growth | +23.42% | +6.55% |
| CAGR | +23.44% | +6.55% | |
| Sharpe ratio | 0.63 | 0.23 | |
| Max drawdown | 31.43% | 36.30% | |
| Max daily drop | 8.34% | 6.14% | |
| Max wkly drop | 11.47% | 12.99% | |
| 5Y | Growth | +14.31% | +36.59% |
| CAGR | +2.71% | +6.44% | |
| Sharpe ratio | 0.12 | 0.22 | |
| Max drawdown | 41.43% | 44.57% | |
| Max daily drop | 22.93% | 12.92% | |
| Max wkly drop | 28.23% | 19.51% | |
| 10Y | Growth | +25.35% | +163.21% |
| CAGR | +2.72% | +10.17% | |
| Sharpe ratio | 0.15 | 0.33 | |
| Max drawdown | 62.64% | 68.56% | |
| Max daily drop | 22.93% | 23.32% | |
| Max wkly drop | 28.23% | 30.06% |
| Category | DBX | BOX |
|---|---|---|
| Company | Dropbox, Inc. | Box, Inc. |
| Sector | Technology | Technology |
| Industry | N/A | N/A |
| Core business | Cloud storage and collaboration platform used by individuals, teams, and businesses to sync, share, and store files. Dropbox is pivoting toward AI-powered document workflows through DocSend and AI document management features to add value beyond simple file sync. | Enterprise content management and secure cloud storage platform used by large organizations for compliance, workflow automation, digital signatures (Box Sign), and secure file collaboration. Box targets regulated industries (healthcare, finance, legal) with its security and compliance focus. |
| Investor focus | Average revenue per paying user (ARPU) growth, AI feature adoption driving upsell, free cash flow generation, and whether Dropbox can retain users against Microsoft OneDrive bundling. | Enterprise contract expansion, Box AI workflow automation adoption, suites vs platform pricing, and operating margin improvement toward free cash flow generation. |
- Dropbox generates significant free cash flow relative to its market cap — one of the most cash-generative SMB SaaS companies
- Strong brand recognition among individual professionals and small teams who adopted Dropbox before Microsoft bundled OneDrive
- DocSend and AI document analytics provide workflow tools that add value beyond storage
- Enterprise focus on regulated industries creates strong compliance and security moat vs consumer-grade storage alternatives
- Box AI and workflow automation add value beyond storage, supporting price expansion with existing enterprise customers
- Tight integrations with Microsoft 365, Salesforce, and Google Workspace make Box a complementary layer rather than a competitor
- Microsoft OneDrive and Google Drive bundled with Microsoft 365 and Google Workspace represent persistent structural headwinds
- Paying user growth has plateaued — revenue growth depends on ARPU expansion rather than new user acquisition
- AI document management is a crowded space with Microsoft Copilot as a formidable competitor
- Microsoft SharePoint and OneDrive continue to compete with Box in enterprise content management
- Box's revenue growth has been modest — suites pricing helps ARPU but customer expansion has been slow
- Salesforce's acquisition of Quip and Microsoft's SharePoint improvements reduce workflow collaboration differentiation
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