AI Reshapes B2B Software: Winners and Losers of 2026
Security and consumption-based models thrive while seat-priced platforms struggle.
1Market Recovery Amid Divergence
The iShares Expanded Tech-Software ETF (IGV) surged 40% from April lows to $106.81 by September 3, with August alone seeing 16% gains. However, performance varied wildly among constituents: CrowdStrike rose 83% while monday.com fell 36%. Jefferies analysts noted AI displacement fears were overblown, yet a 117-point performance spread emerged between similar-growth companies like Twilio (+73.8%) and monday.com (-35.5%).
2AI Workloads Define Winners
Security and data platforms benefiting from AI adoption led the rebound. CrowdStrike's Falcon Flex ARR skyrocketed 101% to $2.29B (39% of total ARR), while Snowflake posted 37% product revenue growth in Q2 FY27. Datadog added 750+ AI customers, including all top 10 AI firms. These consumption-based models capitalize on increased data traffic, logs, and attack surfaces from AI deployments.
3The Consumption Pricing Advantage
Platforms billing per usage saw 54-83% gains. Snowflake's revenue hit $1.49B in Q2 FY27 with accelerating growth, while Twilio's $1.5B Q2 revenue grew 22%. Their pricing models automatically benefit from AI's data explosion - whether queries (Snowflake), telemetry (Datadog), or security logs (CrowdStrike). George Kurtz explicitly linked CrowdStrike's 83.4% rise to AI-expanded attack surfaces.
4Enterprise Comeback Stories
Salesforce rebounded from a 29.5% YTD drop in April to finish +4.3%, recovering most losses in August after reporting $1.5B Agentforce ARR. Atlassian staged the most dramatic turnaround: down 57% in March, it jumped 88% in August after disclosing 1M+ users for its AI server tools. Both cases show reratings followed concrete evidence of AI revenue streams, not just growth metrics.
5Seat-Priced Platforms Struggle
HubSpot (-33.3%) and monday.com (-35.5%) suffered despite decent growth (20% and 22% respectively). HubSpot's net customer adds missed targets by 2,000-3,000, with retention slipping to 102%. monday.com's shift to consumption pricing for AI products (now 17% of new ARR) failed to impress markets. Both face lengthening sales cycles as enterprises scrutinize recurring seat licenses amid AI budget shifts.
6Private Market Parallels
The valuation reset extended beyond public markets. Airtable, once valued at $12B in 2021, sold to Bending Spoons for under $1.3B - an 89% drop. This mirrors public software multiples compression, where companies like Salesforce traded 30% below December 2025 highs before recovering. Private investors now demand clearer paths to AI-driven revenue.
7Security's AI Tailwinds
CrowdStrike's 83% surge highlights security as the clearest AI beneficiary. Its $5.84B ARR (growing 25% YoY) reflects how AI expands attack surfaces faster than defenses can adapt. Falcon Flex's 101% ARR growth to $2.29B shows enterprises prioritizing flexible security spending. Unlike seat-based tools, CrowdStrike's usage pricing captures value from every new AI deployment.
8Datadog's Cautionary Tale
Despite 35.6% Q2 2026 growth and 750+ AI customers, Datadog plunged 19% on August 6 - its worst drop since 2019 - when disclosing reduced usage by its largest client. This exposes the double-edged sword of consumption models: they magnify upside from AI workloads but create customer concentration risks. The incident triggered sector-wide volatility.
9The Multiple Reset Factor
Performance gaps partly reflect January 2026 starting valuations. Companies like Snowflake (37% growth) and Twilio (22% growth) traded at 10x and 6x forward sales respectively entering the year. Those carrying premium multiples (HubSpot at 15x) faced steeper corrections when growth metrics softened. AI revenue potential later became the key rerating driver.
10The New Software Playbook
2026's lesson: AI reshuffled software value chains. Winners either bill per usage (capturing AI's data explosion) or secure budgets AI can't displace (cybersecurity). Losers rely on seat-based pricing facing extended sales cycles. With $2T+ in market cap at stake, the divide suggests lasting structural change - consumption models now dictate enterprise software investing.
Original article: SaaStr — AI Reshapes B2B Software: Winners and Losers of 2026