Cassie Pless

Cassie Pless is an experienced sales professional currently serving as Head of Sales at unstructured.io since September 2024. Previously, Cassie worked as a GTM Advisor at Point72 Ventures for a brief period in 2024 and held the role of VP of Sales at Lexion, a company acquired by Docusign. Cassie’s extensive background includes senior positions at Outreach, where responsibilities included Sr. Director and Director of Commercial Sales, and at Zipwhip as Manager of Mid-Market Sales in the West Region. Prior roles also encompass strategic human capital management at ADP and sales leadership at Egencia, managing a team of account executives. Cassie began the career with roles in sales and market development, culminating in notable achievements such as the President’s Club Award in 2015 for exceeding performance quotas. Cassie holds a degree from the UW Foster School of Business.