Cio Bulletin
Contracts form the backbone of any successful organization, driving business through agreements and commitments. Managing them effectively can be a challenging task. That’s where CobbleStone Software comes in. With nearly 30 years of expertise, CobbleStone has revolutionized how organizations manage contracts, procurement, and vendor relationships. Trusted worldwide, CobbleStone empowers organizations to stay compliant, organized, and ahead of their obligations.
Founded in 1995, CobbleStone was among the first to introduce contract management software, and they’ve remained leaders ever since. Their cloud-based and on-premise solutions are trusted by hundreds of organizations across industries, including governments and regulated sectors. Managing over three million contract transactions worth billions of dollars, CobbleStone’s platform is built for reliability and ease of use.
Integrated with leading tools like Microsoft, Oracle, DocuSign, and Salesforce, their software provides flexibility and efficiency. Recognized by industry giants like Gartner and Forrester, CobbleStone ensures their clients stay ahead of compliance and operational challenges. At its core, CobbleStone is driven by a mission to deliver cutting-edge, cost-effective, and user-friendly solutions.
At CIO Bulletin, we had the privilege of interviewing Mark Nastasi, Founder and Executive VP of CobbleStone Software. He shared valuable insights into how he and his company are creating solutions that help organizations avoid costly mistakes, streamline operations, and focus on what they do best—making contract management simple and accessible.
Interview Highlights
CobbleStone Software has been a pioneer in contract management since its inception in 1995. Could you share the story behind the founding of the company and the inspiration that sparked its creation?
Founded in 1995, CobbleStone Software was one of the pioneers in providing contract tracking and management solutions. The inspiration for this innovation stemmed from a costly incident in which a prominent company unintentionally breached a contract, resulting in a multimillion-dollar settlement. In response, CobbleStone Software set out to help organizations avoid similar pitfalls by delivering a more effective way to manage contracts and fulfill obligations.
CobbleStone Software is recognized as one of the "10 Great Places to Work 2025." What initiatives or values contribute to building such a positive and innovative workplace culture?
CobbleStone Software’s recognition as one of the “10 Great Places to Work 2025” is a testament to its commitment to fostering an inclusive, innovative, and supportive workplace culture. Several key initiatives and values contribute to this accolade:
Accessibility and Inclusion: CobbleStone ensures its workplaces in Somerdale and Lindenwold are accessible, with wheelchair ramps and ADA-compliant bathrooms. The company also meets WCAG compliance standards for web accessibility, making its digital platforms inclusive for individuals with disabilities. Additionally, CobbleStone promotes diversity and inclusion throughout the office with visible reminders and fosters equality through its supplier and partner program, prioritizing partnerships with women-owned and disadvantaged businesses.
Community Engagement & Social Responsibility: CobbleStone actively gives back, investing 5% of its revenue into charitable causes and communities. As a company, it participates in numerous initiatives, such as Feeding the Homeless, Wreaths Across America, Community Cleanups, and events with local senior living facilities and animal shelters. CobbleStone also donates books from its onsite lending library to local recovery centers and most recently conducted a toy drive for the 2024 end-of-year holiday season. As a member of the UN Compact for Chance, CobbleStone is a proud supporter of global efforts in sustainable agriculture, education, water, and food equality.
Through these initiatives, CobbleStone hopes to continue cultivating a workplace that values accessibility, social impact, and innovation – solidifying its reputation as an outstanding organization.
Can you elaborate on the range of products and services offered by CobbleStone Software and how they cater to the unique needs of your diverse client base?
CobbleStone Software offers a robust suite of products and services designed to meet the diverse needs of its clients across industries. Its flagship solution, CobbleStone Contract Insight®, streamlines contract lifecycle management (CLM) with features such as automated workflows, eSignature software, and advanced analytics. Other offerings include vendor management, procurement, eSourcing, and legal document management tools, all of which are configurable and scalable for organizations of all sizes. CobbleStone also offers tailored implementation, technical support, custom development, and system training for users through CobbleStone University to ensure clients maximize the value of their solutions.
Serving industries like healthcare, government, education, pharmaceuticals, energy/utilities, and financial services, CobbleStone delivers industry-specific features to address unique challenges. For instance, healthcare clients benefit from compliance with HIPAA regulations, while government organizations gain tools for audit trails and reporting. By offering flexible, secure, and highly configurable software solutions alongside exceptional support, CobbleStone empowers organizations to enhance efficiency, reduce risks, and achieve their goals.
CobbleStone Software offers innovative tools like VISDOM® AI and ConfigAISM. How do these technologies revolutionize the way businesses manage contracts and mitigate risks?
CobbleStone Software’s innovative technologies, VISDOM® AI and ConfigAI, transform how businesses manage contracts and mitigate risks by leveraging artificial intelligence to enhance efficiency, accuracy, and decision-making. VISDOM® AI extracts and analyzes contract data to identify potential risks, suggest optimal contract terms, and provide actionable insights for compliance and performance improvement. Its ability to automate contract review and flag inconsistencies reduces human error and accelerates the contract drafting and negotiation processes, enabling organizations to make informed, data-driven decisions.
ConfigAISM simplifies clause data configuration, allowing businesses to tailor CobbleStone’s platform to their unique workflows without extensive technical expertise. By automating field configuration for contract clauses, ConfigAISM ensures a smooth user experience. Together, these tools empower organizations to optimize contract lifecycle management, proactively manage risks, and improve operational efficiency—giving them a competitive edge in today’s fast-paced business environment.
To learn more about these technologies and their impact on contract management, visit the following links:
With features like IntelliXtract and Auto-Redline, CobbleStone is redefining contract oversight. Could you discuss the role of artificial intelligence in enhancing the efficiency and accuracy of contract management?
CobbleStone Software leverages artificial intelligence (AI) through features like IntelliXtract and auto-redline to revolutionize contract oversight by enhancing both efficiency and accuracy. IntelliXtract uses AI to extract key data points from contracts and related documents, automating the often time-consuming process of manual data entry. This automation ensures that critical information, such as renewal dates and compliance requirements, is captured accurately, enabling businesses to move proactively and avoid costly oversights.
With auto-redline, users are able to streamline contract review by automatically replacing introduced clauses with their organization’s preferred clause language and highlighting changes, reducing the risk of missed edits or errors. AI-powered tools like these not only save time but also improve precision, allowing legal and procurement teams to focus on strategic decision-making rather than repetitive tasks. By incorporating AI into its contract lifecycle management software solution, CobbleStone empowers organizations to manage contracts more effectively, mitigate risks, and enhance overall productivity.
Your software boasts integrations with major platforms like Microsoft, Oracle, DocuSign, and Salesforce. How do these partnerships amplify the capabilities of CobbleStone’s solutions?
CobbleStone Software’s integrations with platforms like Microsoft, Oracle, DocuSign, and Salesforce enhance its contract lifecycle management solutions by allowing users to streamline their existing workflows and connect key business tools. The integration with Microsoft Office enables users to create and edit contracts seamlessly, while Oracle compatibility fosters smooth data synchronization with ERP systems. The DocuSign integration facilitates secure, efficient eSignatures, and Salesforce integration empowers sales teams to manage contracts hand-in-hand with their CRM. These partnerships amplify CobbleStone’s functionality, providing a unified platform that boosts efficiency and leverages the best-in-class tools organizations already rely on.
Employee satisfaction is often a hallmark of great workplaces. How does CobbleStone ensure the well-being, growth, and engagement of its employees?
Employee health and safety are company priorities, with compliance to OSHA regulations and both federal and local labor laws. These regulations are posted clearly and visibly onsite and virtually for employee education and transparency. CobbleStone also offers an Employee Assistance Program (pending approval) and an employee appreciation table to create a positive workplace atmosphere. Additionally, CobbleStone offers its employees flexible schedules, hybrid or remote work options, and a tuition reimbursement program, which further demonstrates its dedication to supporting employees’ personal and professional growth.
CobbleStone has a mission to evolve continuously to meet modern-day business needs. What exciting developments or innovations can we expect from CobbleStone in the near future?
CobbleStone takes pride in continuing its mission to evolve continuously to meet modern-day business needs. One of its more recent and exciting innovations has been its AI solution, VISDOM, backed by machine learning. CobbleStone has taken VISDOM to the next level with VISDOM+, its all-new generative AI solution, built on OpenAI—the makers of ChatGPT. With VISDOM+, users can take advantage of smarter contracts to streamline their contracting process. Users have access to features like AI Assist, a helpful and engaging chatbot to answer questions about CobbleStone Contract Insight. Users also have access to additional features allowing them to generate clauses, with the ability to centralize generated clauses as well. With VISDOM+, users can take full advantage of enhanced risk & language analysis, leveraging statistics, AI, ML, contract sentiment analysis, and advanced analytics to their fullest.
The Stalwart Leader behind CobbleStone Software’s Unwavering Success
Mark Nastasi is the Founder and Executive VP of CobbleStone Software. He brings over 20 years of professional experience in the industry. In 1995, he pioneered the launch of the first commercial contract software, CMTS (Contract Management Tracking System). Throughout his career, Mark has collaborated extensively with general counsels, paralegals, lawyers, and legal professionals to enhance contract management practices.
You can reach Mark via email at mnastasi@cobblestonesoftware.com
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