

Datadog vs Zscaler
Enterprise cloud monitoring and analytics platform vs Cloud security company replacing older network hardware. Which is the better buy for your portfolio in September 2026? Plain-English answer below.
Datadog has built an observability platform that consolidates logging, monitoring, and security for cloud-native applications into a single agent with powerful land-and-expand economics, while Zscaler delivers cloud-based zero-trust network security that replaces legacy VPN and firewall infrastructure for enterprise customers. Both companies sell essential infrastructure software to large enterprises navigating digital transformation, and both generate durable net revenue retention rates that make their growth stories highly visible. Datadog vs Zscaler examines rule-of-40 performance, competitive positioning in adjacent markets, and path to sustainable profitability for two of the cloud security and observability sector's most closely watched names.
Datadog has built an observability platform that consolidates logging, monitoring, and security for cloud-native applications into a single agent with powerful land-and-expand economics, while Zscaler...
Why It’s Moving

Datadog Rallies on AI Infrastructure Momentum and Enterprise Adoption
- The stock rose approximately 5% during a session where Fastly surged 14% on an AI firewall launch, indicating strong investor appetite for AI-adjacent infrastructure plays.
- Recent analysis points to accelerating enterprise customer expansion, fueled by the increasing adoption of AI-driven observability and security solutions across large organizations.
- While facing some near-term customer pressure, Datadog continues to deliver stronger revenue growth compared to competitors like Fortinet, maintaining its position as a key player in cloud security.

Zscaler targets AI-driven growth with upcoming investor day and surging bookings
- The company announced it will host an Investor Day on October 6, featuring leadership presentations on long-term growth drivers and financial outlook.
- AI-related bookings jumped more than 50% sequentially in Q4'26, signaling rising demand for Zscaler's security solutions in the AI era.
- Analysts noted that shares are trading at a discount to historical valuations, with some highlighting potential upside despite missing out on earlier sector rallies.

Datadog Rallies on AI Infrastructure Momentum and Enterprise Adoption
- The stock rose approximately 5% during a session where Fastly surged 14% on an AI firewall launch, indicating strong investor appetite for AI-adjacent infrastructure plays.
- Recent analysis points to accelerating enterprise customer expansion, fueled by the increasing adoption of AI-driven observability and security solutions across large organizations.
- While facing some near-term customer pressure, Datadog continues to deliver stronger revenue growth compared to competitors like Fortinet, maintaining its position as a key player in cloud security.

Zscaler targets AI-driven growth with upcoming investor day and surging bookings
- The company announced it will host an Investor Day on October 6, featuring leadership presentations on long-term growth drivers and financial outlook.
- AI-related bookings jumped more than 50% sequentially in Q4'26, signaling rising demand for Zscaler's security solutions in the AI era.
- Analysts noted that shares are trading at a discount to historical valuations, with some highlighting potential upside despite missing out on earlier sector rallies.
Investment Analysis

Datadog
DDOG
Pros
- Datadog is a leading provider of cloud-based monitoring and analytics solutions with a strong industry position.
- It has shown consistent revenue growth driven by the increasing demand for observability and IT operations tools.
- Its risk profile includes moderate volatility, facilitating portfolio diversification with some positive correlation to peers.
Considerations
- The company's return on equity (ROE) is relatively low at 4.35%, below many industry peers, indicating moderate profitability.
- Datadog's risk-adjusted performance, such as the Sharpe ratio of 0.06, is significantly weaker compared to competitors like Zscaler.
- Price volatility is somewhat high at 11.87%, reflecting larger price fluctuations that may increase investment risk.

Zscaler
ZS
Pros
- Zscaler is a major player in cloud security with a market capitalization slightly above $44 billion, similar in scale to Datadog.
- It exhibits stronger risk-adjusted returns, with a Sharpe ratio of 1.31, suggesting better risk management and return balance.
- Zscaler has slightly lower price volatility (11.14%) compared to Datadog, implying relatively steadier price movements.
Considerations
- Despite its scale and growth, Zscaler operates in a competitive cyber security space with significant rivals like CrowdStrike and Palo Alto Networks.
- The stock shows moderate price fluctuations which still indicate notable investment risk in a volatile sector.
- Its valuation and profitability metrics may be pressured by ongoing innovation demands and pricing competition within cloud security.
Datadog (DDOG) Next Earnings Date
Datadog’s next earnings release is expected on November 5, 2026. The report will cover the third quarter of fiscal 2026, ending September 2026. The date remains an estimate, but it is consistent with the company’s historical early-November reporting pattern.
Zscaler (ZS) Next Earnings Date
Zscaler (ZS) is expected to report its next earnings on November 24, 2026. The report will cover the company’s fiscal first quarter of 2027, ended October 31, 2026. The date remains an estimate, but it aligns with Zscaler’s historical reporting schedule and current earnings-calendar data.
Datadog (DDOG) Next Earnings Date
Datadog’s next earnings release is expected on November 5, 2026. The report will cover the third quarter of fiscal 2026, ending September 2026. The date remains an estimate, but it is consistent with the company’s historical early-November reporting pattern.
Zscaler (ZS) Next Earnings Date
Zscaler (ZS) is expected to report its next earnings on November 24, 2026. The report will cover the company’s fiscal first quarter of 2027, ended October 31, 2026. The date remains an estimate, but it aligns with Zscaler’s historical reporting schedule and current earnings-calendar data.
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