What was the first thing that came to your mind when you heard that Coupa has acquired Cirtuo?
You know what mine was?
Oracle, PeopleSoft, and JD Edwards. That deal happened twenty years ago, so what does it have to do with today’s Coupa-Cirtuo news? Everything.
Here is the preliminary output from my 4-Model RAM Assessment:
MODEL 1 (PRELIMINARY)
The establishment narrative often frames acquisitions like Oracle’s and Coupa’s as unequivocal wins for innovation and market growth, but this glosses over real challenges. Oracle’s deal succeeded in expanding its market share but at the cost of significant customer and partner discontent, with long-term benefits (e.g., Fusion) taking years to materialize. Coupa’s acquisition of Cirtuo follows a similar playbook—enhancing AI capabilities to stay competitive—but the 30–50% success rate of ProcureTech AI implementations (as discussed previously) suggests a high risk of failure if integration, data quality, or user adoption isn’t prioritized. The narrative also downplays competitive retaliation; just as SAP gained in China during Oracle’s turmoil, Oracle or other S2P players could exploit any missteps by Coupa. Both deals highlight the tension between strategic ambition and operational reality, with success hinging on execution rather than acquisition alone.
MODEL 2 (PRELIMINARY)
The recent Coupa acquisition of Cirtuo in 2024–2025 mirrors elements of Oracle’s acquisition of PeopleSoft (and by extension JD Edwards) from the early 2000s in both strategic value and controversy.
THE GOOD PARALLELS
Theme
Oracle + PeopleSoft
Coupa + Cirtuo
Strategic Market Expansion
Oracle expanded from databases to enterprise apps (ERP, HR).
Coupa expanded from P2P/S2P into AI-driven category strategy.
Tech Synergy
Oracle gained PeopleSoft’s HR/payroll and JDE’s mid-market ERP tools.
Coupa gains Cirtuo’s category strategy intelligence platform, enhancing its AI narrative.
Customer Base Consolidation
Oracle gained access to over 12,000 PeopleSoft clients.
Coupa now owns the leading platform in strategic sourcing advisory, giving it a strong competitive edge in upstream procurement.
Vision Extension
Oracle wanted to offer end-to-end enterprise software.
Coupa seeks to evolve into an end-to-end cognitive procurement platform.
Analytics Play
Oracle leveraged PeopleSoft’s BI stack.
Cirtuo strengthens Coupa’s Category Strategy Studio with structured AI reasoning.
THE BAD PARALLELS
Theme
Oracle + PeopleSoft
Coupa + Cirtuo
Community Distrust
Many PeopleSoft users feared Oracle would kill innovation or sunset overlapping products.
Cirtuo’s loyal base (especially among category managers) fear Coupa may over-commercialize or dilute its advisory roots.
Cultural Clash
Oracle (aggressive, sales-driven) vs. PeopleSoft (customer-centric).
Coupa (Silicon Valley SaaS scale) vs. Cirtuo (boutique, strategic sourcing think tank).
Integration Risk
Took years to rationalize product overlaps and support contracts.
Coupa risks confusing or complicating the Cirtuo UX, especially if they push tight integration too early.
Innovation Slowdown
PeopleSoft R&D pipeline stagnated after acquisition.
There’s concern Coupa may prioritize monetization over Cirtuo’s strategic roadmap (like its stand-alone AI coaching capabilities).
Client Lock-in
Oracle forced migrations or bundled pricing.
Coupa may bundle Cirtuo functionality into platform tiers, limiting access for non-Coupa customers.
STRATEGIC SIMILARITY SNAPSHOT
Attribute
Oracle–PeopleSoft/JDE
Coupa–Cirtuo
Acquisition Type
Defensive + Expansion
Opportunistic + Strategic Reinforcement
Technology Overlap Risk
High (overlapping ERP modules)
Low-to-moderate (Cirtuo is more upstream)
Culture Compatibility
Low
Moderate
Customer Impact
Mixed (short-term disruption, long-term scale)
Likely mixed — improved suite, possible strategic tension
Summary
Coupa’s acquisition of Cirtuo echoes Oracle’s PeopleSoft play in how it:
Strengthens its suite via strategic tuck-in,
Risks alienating a loyal user base, and
Transforms internal culture dynamics between scale and strategy.
The difference? Cirtuo is more specialized and less infrastructure-heavy than PeopleSoft, making integration easier technically — but culturally just as fragile.
MODEL 3 (PRELIMINARY)
The acquisition of Cirtuo by Coupa mirrors aspects of Oracle’s contentious 2003–2005 acquisitions of PeopleSoft and JD Edwards, reflecting both strategic opportunities and historical pitfalls.
Conclusion
The Coupa-Cirtuo deal reflects the “good” of strategic acquisitions-filling capability gaps and accelerating innovation-while cautiously navigating the “bad” of integration pitfalls. Unlike Oracle’s aggressive consolidation, Coupa is leveraging Cirtuo’s AI expertise to advance a collaborative, data-driven vision. However, the true test lies in execution: avoiding Oracle’s missteps requires maintaining Cirtuo’s agility, ensuring customer-centricity, and delivering on the promise of autonomous spend management. If successful, Coupa could redefine procurement tech much like Oracle reshaped ERP-but with AI as the differentiator, not a disruptor.
MODEL 4 (PRELIMINARY)
The procurement and enterprise software landscapes have been shaped significantly by strategic acquisitions. This report examines how Coupa’s recent acquisition of Cirtuo (announced May 13, 2025) mirrors both the strengths and weaknesses of Oracle’s landmark purchase of PeopleSoft and JD Edwards (completed in 2005).
These acquisitions, while separated by two decades, represent pivotal moments in the evolution of business software platforms and offer valuable insights into the dynamics of technology integration, market consolidation, and customer impact in the enterprise software sector.
By comparing the strategic intent, execution approach, integration challenges, and early outcomes of both deals, we can identify patterns that may predict Coupa’s future success or potential pitfalls.
THE REAL MEASUREMENT OF M&A SUCCESS
In the next few posts, I will examine several significant ProcureTech implementations over the past 25 years and the long-term benefits they delivered for investors, founding owners, and, most importantly, practitioner clients.
Procurement Insights
Oracle, PeopleSoft, JD Edwards and Coupa’s Acquisition of Cirtuo
Posted on May 14, 2025
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What was the first thing that came to your mind when you heard that Coupa has acquired Cirtuo?
You know what mine was?
Oracle, PeopleSoft, and JD Edwards. That deal happened twenty years ago, so what does it have to do with today’s Coupa-Cirtuo news? Everything.
Here is the preliminary output from my 4-Model RAM Assessment:
MODEL 1 (PRELIMINARY)
The establishment narrative often frames acquisitions like Oracle’s and Coupa’s as unequivocal wins for innovation and market growth, but this glosses over real challenges. Oracle’s deal succeeded in expanding its market share but at the cost of significant customer and partner discontent, with long-term benefits (e.g., Fusion) taking years to materialize. Coupa’s acquisition of Cirtuo follows a similar playbook—enhancing AI capabilities to stay competitive—but the 30–50% success rate of ProcureTech AI implementations (as discussed previously) suggests a high risk of failure if integration, data quality, or user adoption isn’t prioritized. The narrative also downplays competitive retaliation; just as SAP gained in China during Oracle’s turmoil, Oracle or other S2P players could exploit any missteps by Coupa. Both deals highlight the tension between strategic ambition and operational reality, with success hinging on execution rather than acquisition alone.
MODEL 2 (PRELIMINARY)
The recent Coupa acquisition of Cirtuo in 2024–2025 mirrors elements of Oracle’s acquisition of PeopleSoft (and by extension JD Edwards) from the early 2000s in both strategic value and controversy.
THE GOOD PARALLELS
THE BAD PARALLELS
STRATEGIC SIMILARITY SNAPSHOT
Summary
Coupa’s acquisition of Cirtuo echoes Oracle’s PeopleSoft play in how it:
The difference? Cirtuo is more specialized and less infrastructure-heavy than PeopleSoft, making integration easier technically — but culturally just as fragile.
MODEL 3 (PRELIMINARY)
The acquisition of Cirtuo by Coupa mirrors aspects of Oracle’s contentious 2003–2005 acquisitions of PeopleSoft and JD Edwards, reflecting both strategic opportunities and historical pitfalls.
Conclusion
The Coupa-Cirtuo deal reflects the “good” of strategic acquisitions-filling capability gaps and accelerating innovation-while cautiously navigating the “bad” of integration pitfalls. Unlike Oracle’s aggressive consolidation, Coupa is leveraging Cirtuo’s AI expertise to advance a collaborative, data-driven vision. However, the true test lies in execution: avoiding Oracle’s missteps requires maintaining Cirtuo’s agility, ensuring customer-centricity, and delivering on the promise of autonomous spend management. If successful, Coupa could redefine procurement tech much like Oracle reshaped ERP-but with AI as the differentiator, not a disruptor.
MODEL 4 (PRELIMINARY)
The procurement and enterprise software landscapes have been shaped significantly by strategic acquisitions. This report examines how Coupa’s recent acquisition of Cirtuo (announced May 13, 2025) mirrors both the strengths and weaknesses of Oracle’s landmark purchase of PeopleSoft and JD Edwards (completed in 2005).
These acquisitions, while separated by two decades, represent pivotal moments in the evolution of business software platforms and offer valuable insights into the dynamics of technology integration, market consolidation, and customer impact in the enterprise software sector.
By comparing the strategic intent, execution approach, integration challenges, and early outcomes of both deals, we can identify patterns that may predict Coupa’s future success or potential pitfalls.
THE REAL MEASUREMENT OF M&A SUCCESS
In the next few posts, I will examine several significant ProcureTech implementations over the past 25 years and the long-term benefits they delivered for investors, founding owners, and, most importantly, practitioner clients.
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