Data Science Institute

Ben Clayman is a seasoned engineering leader currently serving as a Director of Engineering, Data & Applied AI at Toast, where he oversees critical technical initiatives for the cloud-based restaurant software platform.

Before joining Toast, Ben built a distinguished career at Square, holding several key leadership roles. Most notably, he served as the Engineering Lead for Square Checking, Square Savings, and Early Revenue Access, managing the core systems behind Square Banking. Prior to that, he held roles as a backend payments engineer and a machine learning engineer, building Square’s first models for customer support and compliance. 

While in graduate school, he was a part of the Carnegie Mellon University research team that developed the world’s first superhuman poker AI—a landmark achievement in machine learning.

Ben is a passionate advocate for professional development and “enabling the motivated.” He specializes in mentorship and workforce mobility, with a particular focus on helping individuals from non-traditional backgrounds successfully navigate career transitions and role switches within the tech industry.

Ben holds an M.S. in Computer Science from Brandeis University and an A.B. in Philosophy from Brown University.