Mark Nastasi: Contract lifecycle management has undergone a profound transformation over the past few decades. What once relied on manual processes and disconnected systems has evolved into a strategic function driven by automation, data intelligence, and increasingly sophisticated regulatory demands. Organizations now expect their CLM platforms to streamline workflows, strengthen compliance, mitigate risk, and deliver insights that shape high-level decisions. This shift has been propelled not only by technology, but, by the vision of leaders who recognized early that contracts would become central to enterprise strategy.
Among those leaders is Mark Nastasi, whose career in legal technology spans more than 30 years. In 1995, he introduced the Contract Management Tracking System (CMTS) after identifying a pressing need for organizations to manage agreements with greater structure and visibility. What began as a solution to organize paper-heavy processes soon grew into a broader mission: elevating contract management from a routine administrative task to a core driver of operational efficiency and business intelligence.
For more than two decades, Nastasi has guided CobbleStone Software through a rapidly evolving CLM landscape shaped by tightening regulations, accelerated digital transformation, and increasing expectations for contract analytics. Under his leadership, CobbleStone has advanced from an early pioneer of digital contract storage to a global leader in intelligent, AI-driven contract lifecycle management. Through bold innovation and a client-focused approach, he has positioned the company at the forefront of modern contracting, helping organizations worldwide work smarter, negotiate better, and unlock measurable value from their agreements.
Evolving Leadership for a New Era of CLM
When CobbleStone first entered the market, Nastasi’s primary objective was clear: bring order to the messy, paper-based processes that slowed organizations down. The focus was on centralizing contracts, digitizing workflows, and giving teams a single source of truth.
But the industry matured quickly. Organizations began demanding not just structure, but intelligence: tools that interpret risk, improve compliance, surface insights, and support higher-level decision-making. According to Nastasi, that shift rerouted his leadership philosophy. “Our vision evolved from managing contracts to empowering businesses with a platform that adapts to their unique needs,” he explains. Flexibility, configurability, and intelligence became the new non-negotiables.
This evolution led CobbleStone to invest heavily in innovations such as Agentic AI, advanced workflow builders, and predictive analytics, tools designed to anticipate what contract teams need before they even ask.
AI and VISDOM®: Transforming Contract Workflows
Nastasi has long believed that artificial intelligence would redefine the CLM market, and CobbleStone was among the first to embed AI and machine learning into core contract processes. Their proprietary AI engine, VISDOM®, is at the center of this transformation, automatically extracting clauses, identifying risk indicators, and recommending negotiation strategies based on historical data.
“AI turns contract workflows from rigid sequences into living, adaptable processes,” Nastasi says. CobbleStone has expanded this vision with agentic AI tools, sentiment analysis, and AI-powered Outlook and Word plug-ins that seamlessly integrate intelligence into everyday legal work. By automating routine tasks such as review cycles, clause comparisons, and compliance checks, AI frees teams to focus on higher-impact responsibilities. But Nastasi emphasizes that AI must be implemented responsibly with transparency, governance, and always with human oversight.
AI’s Value for Legal Teams: Amplifying Expertise, Not Replacing It
During a recently co-hosted ACC Northeast webinar on AI-driven in-house contract management, Nastasi highlighted what he sees as AI’s biggest advantage: reducing complexity. Legal teams face mounting pressure with more contracts, higher compliance burdens, and aggressive turnaround expectations. AI lightens that load.
Instead of spending hours searching through dense documents, legal professionals can instantly surface crucial clauses, understand negotiation bottlenecks, and improve risk evaluation. “AI doesn’t replace legal expertise, it amplifies it,” he notes. With actionable intelligence and automated workflows, legal teams can make faster, smarter decisions while elevating their strategic role within the organization.
Transforming User Experience With Simplicity and Personalization
As CobbleStone expanded its capabilities, Nastasi recognized that power alone wasn’t enough and that usability had to evolve. Early versions of CobbleStone Contract Insight® focused on functionality, but as the customer base widened, user expectations changed. People wanted interfaces that felt intuitive, experiences tailored to their roles, and dashboards that surfaced only the most relevant insights.
CobbleStone responded with a complete UX overhaul. Customizable dashboards, dynamic record screens, and AI-guided interactions now allow every user, from legal to procurement to finance, to work in an environment shaped around their needs. “Advanced capabilities should feel effortless,” Nastasi emphasizes.
Balancing Innovation With Compliance Across Public and Private Sectors
Serving both the public and private sectors requires agility without sacrificing security. CobbleStone meets stringent standards, including federal guidelines, data center certifications, and strict auditability, while delivering configurable, adaptable workflows. Features such as dynamic approval routing, customizable templates, granular permission settings, and transparent activity logs ensure that contracting, eProcurement and eSourcing processes remain compliant, fair, and accountable.
Versatility paired with governance is the guiding principle. “We build configurability into every layer of the platform so organizations can adopt processes quickly without compromising compliance,” Nastasi explains.
Security by Design: Innovation Without Compromise
To Nastasi, security is not a constraint on innovation, it is a prerequisite. Every new feature, including AI agents and real-time collaboration tools, is grounded in industry-leading safeguards such as SOC-compliant data centers, encryption, multi-factor authentication, and detailed audit trails.
“Trust comes from transparency and control,” he says. Role-based permissions ensure only authorized users access sensitive contract data, while comprehensive logs support accountability across the contract lifecycle. This security-first approach allows clients to confidently adopt advanced technologies without risking data integrity or compliance obligations.
Thought Leadership as a Growth Engine
CobbleStone’s influential framework on the “8 Stages of the Contract Lifecycle” is a cornerstone of the company’s educational mission. Nastasi believes that empowering customers with best practices elevates the entire CLM ecosystem. “Education builds trust and positions us as a true partner, not just a vendor,” he notes. Through webinars, blogs, whitepapers, and training, CobbleStone guides both seasoned and emerging contract teams toward maturity.
Staying Ahead in an Intensifying Competitive Landscape
Despite growing competition, CobbleStone has maintained its leadership, earning recognition from analysts such as QKS Group, which named CobbleStone the Leader in the SPARK Matrix CLM report for four consecutive years. Enterprise clients benefit from deep configurability, while smaller organizations appreciate the platform’s intuitive design, ready-to-use templates, and scalable deployment models.
CobbleStone’s philosophy is clear: sophisticated CLM should be accessible to all organizations, regardless of size.
Mark Nastasi: A Legacy of Empowerment and Responsible Innovation
Looking ahead, Nastasi hopes his legacy is one of transformation, shifting the perception of contracts from administrative paperwork to strategic business assets. His aim is to democratize advanced contract technology and make its benefits tangible for every organization.
“I want CobbleStone to be remembered for trust, transparency, and innovation done responsibly,” he says.
Under Nastasi’s leadership, CobbleStone Software has not only kept pace with an evolving market, it has helped define the future of contract intelligence.
