PayPalDatadog
Live Report · Updated 23 September 2026

PayPal vs Datadog

Global digital payments platform connecting buyers and sellers vs Enterprise cloud monitoring and analytics platform. Which is the better buy for your portfolio in September 2026? Plain-English answer below.

PayPal runs one of the world's largest digital payments networks with hundreds of millions of active accounts, while Datadog operates a cloud observability and monitoring platform serving engineering ...

Why It’s Moving

PayPal

PayPal Shares Rally on Strategic Meta AI Partnership, Though Analysts Eye Long-Term Upside

  • The company announced a checkout deal with Meta that enables shopping via the Muse AI agent, positioning PayPal as a key infrastructure player in the emerging 'everything app' ecosystem.
  • This move follows Shopify's similar adoption of the AI agent just one day prior, signaling a rapid industry shift toward AI-driven commerce integrations.
  • Despite the recent positive momentum from the partnership, the stock faces continued scrutiny due to a significant year-to-date drop and internal investigations into officer conduct.
Sentiment:
🐃Bullish
Datadog

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.
Sentiment:
🐃Bullish

Investment Analysis

PayPal

PayPal

PYPL

Pros

  • PayPal reported a 5% year-on-year revenue growth in Q2 2025 to approximately $8.29 billion, exceeding analyst expectations with adjusted EPS of $1.40.
  • Strategic initiatives, including PayPal World platform, agentic commerce adoption, stablecoin integration, and AI-based solutions, position it for long-term growth.
  • Excess returns analysis shows PayPal is undervalued by over 40%, with a strong return on equity of 24.18% and stable projected EPS of $6.14.

Considerations

  • Growth in branded payments through PayPal and Venmo was weak at 5%, below internal targets, signaling challenges in core transaction volumes.
  • Heightened competition in branded payments and reduced fee structures in Asia pose risks to revenue and profitability expansion.
  • Stock price fell 9% after Q2 earnings despite strong results, reflecting investor caution and a cautious Q3 outlook amid elevated market expectations.

Pros

  • Datadog reported Q3 2025 revenue and earnings that beat Wall Street estimates, driving a 20% stock price surge after the announcement.
  • The company benefits from strong demand for cloud-based software-as-a-service (SaaS) and enterprise monitoring solutions, reflecting growth in digital transformation.
  • With a market cap around $42.89 billion and recent positive analyst reception, Datadog shows continued investor confidence in its execution and growth prospects.

Considerations

  • Datadog’s valuation remains high with a P/E ratio exceeding 250, indicating potential premium pricing relative to earnings.
  • Its share price exhibits considerable volatility, trading in a wide range from $98.80 to $170.08 over the past year, which could indicate market uncertainty.
  • Heavy reliance on tech sector growth and exposure to AI-related market sentiment may introduce cyclicality and valuation risks.

PayPal (PYPL) Next Earnings Date

PayPal Holdings (PYPL) is scheduled to report its fiscal third-quarter 2026 earnings on October 27, 2026. The release is expected before U.S. market opening, followed by the company’s earnings call. This report will cover the quarter ended September 30, 2026.

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.

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