The latest Enterprise Software posts we have indexed from venture capital blogs and newsletters, plus the highest-scoring pieces of the past year and the people who write about it most.
Enterprise AI's real opportunity isn't raw intelligence—it's encoding organizational expertise through continual learning loops that compound across customer deployments, turning AI from a new grad agent into a battle-tested expert that third-party vendors can productize better than internal builds.
Mailchimp's acquisition by Intuit for $12B in 2021 has ended in decline—the platform is now shrinking, with parent company earnings stripped of its figures and management cutting 17% of staff. The fall stems from a seven-year drift away from focus (adding CRM, social, SMS, postcards) combined with a structural shift: AI agents now provision email via API, not UIs, leaving Mailchimp absent from the platforms where new apps are built.
Pear VC solicited startup ideas from founders at Databricks, Uber, Oscar Health, Snowflake, Gusto, and DoorDash, identifying six high-potential startup opportunities spanning AI agents, enterprise governance, personal coaching, and education.
Vertical software incumbents face existential pressure from AI-native competitors but have mostly opted for defensive bolt-ons rather than transformative M&A. The article argues that an acquisition wave is imminent, outlining why incumbents have delayed, what founders should build to become acquisition targets, and how the industry's "Incumbent Adoption Cycle" predicts the timing.
a16z's latest State of Markets reveals compressed valuations for horizontal B2B (2.7x revenue), a stark bifurcation between high-growth startups (500%+) and mature ones, and a unicorn cohort split between aging, unprofitable low-growers and young AI-native companies. Growth now determines valuation multiples far more than profitability.
OpenAI Dev Day revealed a strategic pivot: rather than competing on model superiority alone, the company is building a control plane for AI—integrating persistent agents (Dots), team workspaces, a decisions API, and open-model orchestration—to own the workflow layer even as models commoditize.
Software valuations whipsawed while retention held steady at 109% NRR; consumption-based pricing outperformed, and vertical software suffered disproportionate multiple compression despite stronger fundamentals—likely due to overgeneralized AI-replacement fears in knowledge-work sectors, creating pockets of undervaluation.
The Meritech Software Pulse tracks the $3 trillion public software market, showing a sharp divergence in 2026: AI-enabled infrastructure and security firms outperform, while traditional SaaS faces valuation pressure. Growth now correlates 4.4x more strongly with multiples than profitability, as investors demand revenue acceleration via AI features.
Saastr (67) · Sammy Abdullah (23) · Lenny's Newsletter (9) · Saanya Ojha (7) · A16Z (7) · Tomasz Tunguz (6) · Clouded Judgement (6) · Euclid Ventures (6) · Meritech (5) · Newcomer (4)
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