Darlene Reina

Darlene Reina is the Director of IT & AI Enablement at Babylist, where she leads initiatives spanning enterprise technology, cybersecurity, business applications, automation, and AI adoption. She focuses on building secure, scalable technology foundations and enabling teams to use AI in practical ways that improve operations, decision-making, and the employee experience.

Prior to Babylist, Darlene served as Senior Director of IT and Business Systems at Calendly, where she led programs to modernize internal operations and align technology with business priorities. She helped transform fragmented internal services into a centralized, automated shared-services model while advancing system integrations, employee self-service, and the adoption of AI-enabled tools across the organization.

Drawing on earlier technology leadership roles at Zendesk, Apple, and in higher education, Darlene brings a perspective shaped by scaling technology in high-growth organizations while balancing innovation, security, employee adoption, and organizational change. She believes the best technology removes friction, builds confidence, and gives people the space to do their best work.