In today’s enterprise landscape, the Chief Information Officer is no longer a back-office technologist. The role has evolved into one of strategic orchestration, where technology decisions directly influence risk exposure, regulatory readiness, and long-term competitiveness. Nowhere is this shift more evident than in contract lifecycle management, a discipline that sits at the crossroads of legal oversight, procurement efficiency, and digital transformation. At CobbleStone Software, this convergence is shaped and guided by CIO Matthew Friebis, whose leadership has helped redefine how organizations perceive and manage their contractual foundations.
With contracts governing revenue streams, compliance obligations, and vendor relationships, Friebis views technology not as an enabler of storage, but as an engine for insight. His mandate is clear: transform contract management from a reactive, manual function into a proactive, intelligent system that supports strategic decision-making across the enterprise.
From Infrastructure Leadership to Strategic Technology Stewardship
Matthew Friebis brings more than two decades of enterprise technology leadership to his role as CIO at CobbleStone. His career has been shaped by hands-on experience in large-scale system integrations, cloud modernization initiatives, and the delivery of secure SaaS platforms for highly regulated industries. These milestones established a leadership philosophy grounded in operational excellence, resilience, and measurable business outcomes.
At CobbleStone, Friebis applies this experience to elevate the CIO function beyond infrastructure oversight. He operates as a strategic steward of technology, aligning IT architecture with business goals and client realities. His leadership ensures that CobbleStone Contract Insight does not merely keep pace with digital change, but anticipates it. By embedding scalability, security, and configurability into the core architecture, Friebis has helped position the platform to serve both small teams and global enterprises without compromising performance or governance.
Driving AI Adoption with Trust, Transparency, and Purpose
One of Friebis’ most visible contributions has been guiding the integration of artificial intelligence into CobbleStone’s contract management platform through its proprietary AI/ML engine, VISDOM®. For Friebis, AI adoption is not about innovation for its own sake, but about solving real, high-impact problems while maintaining trust in regulated environments.
Contracts are complex, nuanced, and often unstructured, making AI interpretation a significant technical challenge. Under Friebis’ direction, CobbleStone invested heavily in training AI models across diverse contract datasets, ensuring accuracy in clause extraction, risk identification, and predictive insights. Just as important was the strategic challenge of user confidence. Legal and procurement teams must trust AI outputs, especially when they influence compliance and financial exposure.
To address this, Friebis championed the use of explainable AI principles within VISDOM®, enabling users to understand how insights are generated rather than treating them as opaque recommendations. By introducing AI through targeted use cases such as clause detection and risk sourcing before expanding into predictive analytics, Friebis ensured measurable value while building organizational confidence in AI-driven contract intelligence.
Secure-by-Design Leadership in Regulated Environments
In contract and procurement software, security is inseparable from credibility. Friebis has made this principle foundational to CobbleStone’s technology strategy, reinforcing it through the company’s adoption of the Secure by Design Pledge. Innovation, under his leadership, is never pursued at the expense of compliance or data protection.
Friebis oversees a development lifecycle where security and compliance are embedded from the earliest design stages. New features undergo proactive risk assessments and compliance mapping against frameworks such as SOC-compliant data centers, GDPR, HIPAA, and CMMC. Role-based access controls, encryption, audit trails, and configurable governance settings ensure that clients retain visibility and control at all times.
This approach extends beyond technical safeguards. Friebis emphasizes transparency and accountability, ensuring clients understand not only what the system does, but how it protects their data. Regular testing, continuous monitoring, and strong DevSecOps practices reinforce trust, particularly for public sector organizations and enterprises operating in regulated industries.
Shaping the Future of Contract Management Through Vision and Culture
As CIO, Friebis plays a direct role in shaping CobbleStone’s product roadmap. Feature prioritization is informed by client feedback, regulatory developments, and platform usage data, with a consistent focus on automation, risk reduction, and enterprise integration. Capabilities such as automated redlining, AI-driven clause extraction, e-signatures, eProcurement, and vendor management are developed as interconnected components of a broader contract intelligence ecosystem.
Equally important is how Friebis leads teams through change. He fosters a culture that balances regulatory awareness with innovation speed, ensuring developers understand the legal and procurement implications of their work. The needs of legal and compliance teams are considered early in design, while continuous integration, automated testing, and quality controls maintain reliability at scale.
Looking ahead, Friebis sees generative and agentic AI remaining as a strong force in contract lifecycle management. Intelligent drafting, negotiation support, advanced analytics, and deep automation will further reposition contracts as strategic assets rather than administrative obligations. CobbleStone is preparing for this future by investing in scalable AI frameworks and responsible innovation practices that prioritize security, transparency, and measurable ROI.
What continues to drive Friebis in his leadership role is impact. By aligning technology with real-world client needs, he is helping organizations reduce risk, improve compliance, and unlock insights hidden within their contracts. In a rapidly evolving digital landscape, his vision ensures that CobbleStone remains not just technologically advanced, but strategically indispensable.
