Morningstar Law Group – Raleigh Law Firm – Durham NC Attorneys

Richard Caira is a software and information technology attorney having more than two decades of experience advising technology and other startups, mid-size businesses, and Fortune 500 companies. He provides strategic, practical and timely advice to tech-focused clients looking to commercialize their offerings and grow, while effectively managing risk.

A former in-house lawyer for a multi-billion dollar software company, Richard negotiates complex and sophisticated commercial agreements and advises clients on technology-related issues, including proprietary and open source software, cloud computing, e-commerce, privacy, data security, social media and digital marketing. He also has considerable experience on the other side of the table, regularly assisting technology licensees and users with getting the best and most protective deal possible. As part of his robust startup practice, Richard advises clients on important establishment and evolution issues, such as formation, protection and commercialization of intellectual property, competition, funding and growth.

Another significant portion of Richard’s practice: advising clients on how to structure legally-compliant advertising, branding and promotional campaigns, including sweepstakes, contests, drawings, and loyalty programs. In connection with this and other aspects of Richard’s practice, he regularly counsels clients on how to comply with applicable laws, regulations and guidelines such as the FTC Act, the General Data Protection Regulation (GDPR), the Children’s Online Privacy Protection Act (COPPA), the California Consumer Protection Act (CCPA), the FTC’s Endorsement Guidelines, and negative option and automatic renewal laws, among many others.

Richard has been a car aficionado since his earliest memories, and very much prefers to “row” the gears himself when given the choice. Outside the office, he loves to stay active – often times with friends and his amazingly supportive family – with things like golf, hiking, fishing, endurance events, tennis and softball.

What’s the best piece of advice you have ever received?
Know your client’s business inside and out, as if it were your own. Doing so will enable you to assist them in the best, most effective, and most practical way possible.


  • North Carolina Bar Association, IP Law Section: Outstanding Achievement Pro Bono Award (2000-2001)
  • Leadership Cary (2007-2008)

Representative Experience

  • Spearheaded drafting, negotiating and closing of $50+ million agreement for multi-year procurement of customer experience/document management platform on behalf of a software vendor for a large financial services industry customer
  • Advised content developer on necessary steps and process changes to comply with GDPR, CCPA, TCPA and other applicable privacy and consumer protection laws, and drafted comprehensive terms and conditions of service and privacy policy for implementation across platforms
  • Drafted template agreements for startup technology vendors and advised on formation, financing, IP protection and related issues
  • Negotiated and drafted $50+ million multi-year renewal of auditing software license and related services agreement with Fortune 50 customer for a technology vendor
  • Performed regular comprehensive open source software (OSS) audits for converged infrastructure vendor/developer and rendered advice for improvements and changes to OSS policy
  • Drafted comprehensive terms and conditions and related policies for new loyalty program for parking industry client and provided counseling in connection with related sweepstakes
  • Assisted private hospital with negotiating and closing a $500+ million electronic health records management software system procured from a large and established EMR vendor

Presentations & Publications

Richard frequently speaks on topics such as open source software (OSS), advertising compliance and branding issues, and technology services agreements.


  • “Open Source Software: Evaluating the Opportunities and Risks.” Association of Corporate Counsel, Research Triangle Area Chapter’s “IP-Pulooza.” Co-speaker (2019)
  • “The Explosion of Artificial Intelligence and Machine Learning on In-House Counsel.” Morningstar Law Group CLE. Co-speaker (2018)
  • NCBiotech Social Media Forum, Co-speaker/panelist (2016)
  • “Joint Development Agreements: What Works – and What Doesn’t?” Association of Corporate Counsel, Research Triangle Area Chapter. Speaker (2014)
  • “Cloud Computing,” Association of Corporate Counsel, Research Triangle Area Chapter. Speaker/moderator (2012)
  • “Consumer Protection Updates,” American Bar Association Antitrust Law Section. Speaker (2010–2015)
  • “Outsourcing Issues,” Council for Entrepreneurial Development InfoTech Conference. Speaker/moderator (2005)




  • University of New Hampshire Franklin Pierce School of Law, J.D.
  • Flagler College, B.A., English and Business


  • North Carolina State Bar (1998)


  • NC Amateur Sports (Cycle North Carolina and Powerade State Games): Board of Directors (2017-present)
  • NC Technology Association: Board of Directors (2014–2017)
  • NC Bar Association: Chair, IP Law Section’s Pro Bono Committee (2003-2007)
  • Brand Activation Association Division of Association of National Advertisers: Member
  • Licensing Executives Society: Member
  • International Technology Law Association: Member