On this episode of Alumni @ RopesTalk, host and Ropes & Gray partner Marko Zatylny speaks with Brian Elworthy, general counsel of Toast, a global technology platform built to help restaurants operate, grow and thrive. Brian traces his path from Ropes & Gray associate to leading the legal team at one of the hospitality industry’s most innovative and successful technology companies. He reflects on building sophisticated legal and compliance capabilities in a rapidly scaling business, partnering effectively with business leaders, and balancing legal risk with strategic objectives. Brian also explores the growing influence of AI on the legal profession and shares thoughtful advice for associates considering a move in-house, emphasizing the value of developing deep expertise, sound judgment and professional credibility before making the transition.

On this episode of Alumni @ RopesTalk, the firm’s technology strategy leader Ed Black is joined by Steven Obiajulu, Ropes & Gray alum and founder of legal tech startup UseJunior. Steven shares his journey from MIT and Harvard Law School to Ropes & Gray, where he worked in patent and private equity practices before launching UseJunior. The discussion centers on how AI-powered tools like UseJunior are transforming legal document comparison and workflow efficiency, the importance of data security and compliance, and the broader impact of AI on the legal profession. Steven also emphasizes, “AI isn’t replacing attorneys—it’s transforming how we work and improving outdated processes,” offering a forward-looking view on how technology is enhancing the quality and efficiency of legal services.

On this episode of Ropes & Gray’s Alumni @ RopesTalk podcast, employment, executive compensation, and benefits partner Megan Bisk is joined by alum Dan Krockmalnic, chief operating officer and general counsel at Boston Globe Media. Dan shares his journey from Big Law to his current leadership role, discussing his transition from litigation associate to COO and GC, his experiences producing award-winning content like Murder in Boston, and the valuable lessons learned along the way. Tune in to hear Dan's insights on career development, the importance of mentorship, and his advice for young lawyers.