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

WBSP816: Scale Growth by Learning from Enterprise Software Stories - Oct 2025, Ep 37, an Objective Panel Discussion

Sam Gupta Episode 816

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This week’s enterprise software headlines highlight a market simultaneously accelerating into agentic AI while still wrestling with the structural and legal fallout of past transformation failures. On the innovation front, Genstore’s $10M seed round, Tray.ai’s launch of the Tray Agent Hub, and new agentic releases from Mendix and OutSystems underscore how aggressively vendors are repositioning around autonomous workflows and AI-first orchestration layers. ServiceNow’s unveiling of its AI Experience and Plex’s connected worker integration push the same narrative into IT service management and manufacturing operations, signaling that agentic concepts are no longer confined to experimental edges of the stack. At the same time, a parallel storyline of governance and execution risk is playing out, with Zimmer Biomet’s $172M ERP lawsuit against Deloitte, Europe’s continued delays fixing a troubled Oracle system, Daedong USA’s faltering ERP injunction, and the EU Commission’s investigation into SAP’s practices reinforcing how fragile large-scale enterprise transformations remain. Together, these developments paint a bifurcated 2026 landscape: rapid platform innovation driven by AI ambition on one side, and unresolved accountability, regulatory scrutiny, and implementation risk on the other.

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=m3VmbEsy5uQ
Questions for Panelists?
🔗Sam Gupta: linkedin.com/in/samguptausa/
🔗Robert Kramer: linkedin.com/in/robert-kramer-58239b22/
🔗Kenneth ("Kengon") Gonzalez: linkedin.com/in/kengon/
🔗Thomas Wieberneit: linkedin.com/in/thomaswieberneit/
🔗Charles Brennan: linkedin.com/in/charles-brennan-048901132/

Background Soundtrack: Away From You – Mauro Somm

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