WBSRocks: Scaling Growth with AI, Enterprise Software, and Digital Transformation

WBSP818: Scale Growth by Learning from Enterprise Software Stories - Oct 2025, Ep 38, an Objective Panel Discussion

Sam Gupta Episode 818

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This week’s enterprise software developments underscore a widening gap between rapid AI-driven platform innovation and the unresolved execution risks embedded in large-scale ERP programs. On one side of the ledger, Mendix and OutSystems both advanced their agentic AI roadmaps with new releases aimed at operationalizing autonomous workflows, while ServiceNow’s unveiling of its AI Experience, Sprinklr’s new AI capabilities, and Braze’s product enhancements at Forge 2025 reinforce how aggressively vendors across ITSM, CX, and marketing automation are repositioning around AI-first interaction layers. Salesforce’s latest Slack updates and Upstream Works’ enhanced agent desktop further extend this trend into collaboration and contact center operations, signaling that AI augmentation is now table stakes across front-office and service environments. In parallel, Plex’s expanded connected worker integrations highlight how these same concepts are being pushed into manufacturing execution and workforce enablement, while Cleo’s invoice payment and financing solution reflects growing pressure to modernize B2B financial operations. Yet this innovation narrative is tempered by Daedong USA’s loss of an injunction in its ERP dispute—placing its $11.4 billion suit in jeopardy—which serves as a reminder that beneath the AI acceleration, legacy implementation failures, legal exposure, and governance breakdowns continue to create material risk for enterprises betting on large transformation programs.

In today's episode, we invited a panel of industry analysts for a live discussion on LinkedIn to analyze current enterprise software stories. We covered many grounds including the direction and roadmaps of each enterprise software vendors. Finally, we analyzed future trends and how they might shape the enterprise software industry.

Video: https://www.youtube.com/watch?v=_Arr9GjwOBs

Questions for Panelists?
🔗Sam Gupta: linkedin.com/in/samguptausa/
🔗Robert Kramer: linkedin.com/in/robert-kramer-58239b22/
🔗Michael Fauscette: linkedin.com/in/mfauscette/
🔗Jon W. Hansen: linkedin.com/in/jwhansen/
🔗Jan Burian: linkedin.com/in/janburian/

Background Soundtrack: Away From You – Mauro Somm

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