501 Boylston Street, 10th Floor

Boston, MA 02116



Caroline McCaffery

Caroline McCaffrey outsourced business attorney

Attorney, Member of the Firm

Caroline McCaffery has over 21 years of legal and business experience in both private practice and in-house legal roles. With a passion for technology and helping startups, Caroline focuses her practice on a wide range of corporate and commercial matters, including complex debt and equity financings; mergers & acquisitions, and general corporate and business law issues such as organization, governance, and compliance.

Prior to joining Outside GC, Caroline spent almost a decade serving as General Counsel to two technology startups. As the first in-house attorney with Sailthru, a provider of marketing automation software, Caroline expanded her existing legal skills to include commercial contracts, employment law issues and privacy. She then joined Clarifai, an A.I. computer vision startup, as its General Counsel and VP of Business Affairs, where her added role broadened her experience to non-legal matters such as strategy, finance and information security.

In addition to her legal practice, Caroline is a co-founder of ClearOPS, a third-party risk due diligence company providing knowledge management software for vendors’ privacy and security operations.

She began her legal career as a corporate securities associate at Gunderson Dettmer, LLP in California. After 9/11, Caroline moved back to New York to help build the Gunderson New York office, working primarily with technology startups on what she calls “company-side” work. Caroline is admitted to the New York and California bars, and she is also a certified privacy professional.

Caroline graduated from NYU Law School and received her undergraduate degree from the University of Pennsylvania. She lives just north of New York city with her husband, two kids, an energetic dog and two guinea pigs. Caroline likes to surprise people with the fun fact that she nearly obtained her private pilot’s license and has flown a plane by herself.