Lisa Casson

Co-Founder & COO

Lisa Casson, a Minneapolis native, brings a varied professional background spanning professional sports, event marketing, and technology. Her career began in the fast-paced world of sports and live events, where she honed her ability to manage high-pressure environments, coordinate complex logistics, and support high-profile stakeholders. These early experiences laid the foundation for her deep understanding of operational excellence and relationship management.

Her true passion, however, began to take shape during her time in the Bay Area, where she transitioned into the tech sector and began working closely with executive leadership teams. As a trusted right hand to prominent CEOs - including during her tenure at Yahoo - Lisa played a vital role in navigating product launches, mergers and acquisitions, board and shareholder meetings, and talent onboarding. This work gave her a front-row seat to the inner workings of dynamic, high-growth companies, and deepened her appreciation for the value of strategic, thoughtful support at the executive level.

Lisa is an intuitive problem-solver who understands the demands placed on modern leaders and the importance of having a strong support system. She is energized by building meaningful partnerships between principals and assistants, and is committed to helping both sides succeed.

"The relationship between a principal and their assistant is essential," she says. "The right partnership makes an undeniable impact on both business and personal success. It's not just about efficiency - it's about trust, alignment, and shared goals."

Today, Lisa brings that same passion and perspective to her work at Pennyworth Projects, where she co-leads a boutique executive support and placement agency dedicated to helping leaders thrive. She takes great pride in understanding the nuanced needs of her clients and ensuring that every placement is as strategic as it is personal.