Sasha Peña
Managing Director of Career and Leadership Advancement

With over 11 years of dedicated experience, Sasha Pena has designed and overseen curriculum

development to nurture leadership competencies and essential skills for a seamless transition

from high school to college and onward to successful careers. Her tenure has been marked by a

commitment to bridging the opportunity gap for students, ensuring they are equipped with the

tools needed to thrive in today's workforce and the future of work.

Throughout her career, Sasha has forged valuable relationships with corporate partners, playing a

pivotal role in the design and implementation of Chicago Scholars’ highly successful summer

internship program. Under her guidance, the program has not only provided invaluable hands-on

experience for scholars but has also generate revenue; further solidifying Chicago Scholars'

reputation as a leading force in youth empowerment and career development.

Sasha's deep understanding of the diverse needs spanning various industries, including business,

consulting, finance, accounting, healthcare, and technology, uniquely positions her to spearhead

sales strategies and craft tailored career pathways. Her keen insights into industry trends and

demands enable her to effectively align student aspirations with corporate objectives, ensuring

mutually beneficial partnerships that drive meaningful outcomes.

At the heart of Sasha's role lies a laser-focused approach to understanding and addressing the

intersecting needs of students, colleges, and corporations. With a strategic mindset and an

unwavering dedication to excellence, she navigates the intricate landscape of education and

industry, championing initiatives that empower individuals to realize their full potential.

Currently, Sasha serves as the Head of Employability for REACH Pathways, an ed-tech

company focused on educational equity. Sasha is an alumna of the Surge Fellowship and the

Multicultural Leadership Academy. She is a Chicago native passionate about leadership

development, a youth advocate, and a lifelong learner.