Title: Senior Director, Strategy and Operations
Company: Xchange Chicago, Inc
Location: IL/USA
Education: BS in Mechanical Engineering, Stanford University (2021)
Career History: Senior Director, Strategy and Operations, Xchange Chicago, Inc. (2024-Present); Associate Director, Strategic Development and Operations, Xchange Chicago, Inc. (2022-Present); Chief Executive Officer, Founder, Organic Harvest Digital, Chicago, IL (2019-Present); Hardtech Development Fellow, mHUB, Chicago, IL (2022-2023); Engineering Assistant Lead, Gary Comer Youth Center (Comer Properties), Chicago, IL (2021-2022); National Leadership, Policy Intern, Our Climate, Washington (2020-2021); ASSU Financial Analyst, Stanford Student Enterprises (2019-2021); Student Researcher, The Stanford Precourt Institute for Energy (2020); Sales Operation, PowerReviews (2019); Design Engineer, Student, Stanford University (2019); Project Manager, Stanford Black Scientist and Engineering Society, Stanford University (2017-2019); Economic Adviser, Black Men Initiative, Stanford University (2017-2019); Investment Associate, Venture University, San Francisco Bay Area (2018-2019); Financial Analyst, Concentric Equity Partners, Chicago, IL (2017); Research Assistant, Stanford Engineering Aeronautics and Astronautics, Stanford, CA (2016)
Oluwaseyi G. Olaleye, Senior Director of Strategy and Operations at Xchange Chicago, Inc., has been recognized as a Marquis Emerging Leader for their contributions and achievements in the field of technology.
Born and raised in Nigeria, Mr. Olaleye lived there for the first five years of his life before his family immigrated to the South Shore neighborhood of Chicago. Growing up, he experienced food insecurity firsthand and learned the importance of education, hard work, and community service from his parents at a young age. Although his academic journey was challenging, he excelled as a student and in his senior of high school, an adviser encouraged him to apply to Stanford University. The first in his family to attend college and graduate, he ultimately earned a degree from the institution in mechanical engineering in 2021; as a testament to his determination, he graduated as one of only three Black young men in his cohort.
Throughout his studies, Mr. Olaleye was active as a research assistant with Stanford Engineering Aeronautics and Astronautics, an economic adviser for the university’s Black Men Initiative, a project manager for the Stanford Black Scientist and Engineering Society, and a design engineer. In addition, he gained work experience as a financial analyst with Concentric Equity Partners in Chicago and as an investment associate at Venture University in San Francisco.
In addition, he has found success as the chief executive officer and founder of Organic Harvest since 2019. The hardware startup, the mission of which is to empower communities and nourish the planet through tech innovation, began as a means of enhancing food sustainability in a village in Alaska. Within six months, he and five other Stanford engineering developed a food ecosystem, essentially a food distribution system for the village. He subsequently worked at the Gary J. Coleman Urban Farm, where he built five hydroponic systems for the nonprofit, an initiative that contributed to their success in securing a city grant for a food sovereignty hub.
Upon graduating, Mr. Olaleye was met with various professional opportunities, including his primary employment at Xchange Chicago, Inc., a nonprofit geared to creating tech workforce hubs accessible to all. When he started there as its first official employee in 2022, he served as the associate director of strategic development and operations, responsible for communicating the value proposition to the community and supporting management in securing leases prior to the opening of their new building. Utilizing his entrepreneurial spirit from Stanford and work with several startups, his early roles there encompassed a wide range of responsibilities, from engaging with new stations to help build a stronger brand to leading such initiatives as the Siegel and Walter Family Foundation, which aims to rethink the future of work-ready K-12 spaces.
Since 2024, Mr. Olaleye has excelled as the senior director of strategy and operations, through which he provides comprehensive support for apprentices, focusing on helping individuals and communities break into the tech industry through a variety of right to 14-week programs that include training and a job at its completion—from business analysis to software development and cybersecurity. The company has trained more than 100 individuals and successfully placed around 80 of them into family-sustaining IT tech jobs, which have contributed more than $5 million to the South and West sides of the city.
Looking toward the future, Mr. Olaleye strives to establish a venture fund dedicated to investing in companies, organizations, and communities that operate at the intersection of technology, workforce development, and empowerment. He has long emphasized the importance of establishing a clear pathway for young people to take their first steps in the workforce, especially in an era define by advancements in AI technology.
Mr. Olaleye recently had the opportunity to speak at South by Southwest, which provided him with a platform to showcase the work done with Xchange Chicago on a national scale. The experience was motivational and insightful, allowing him to connect with great people and potential partners who are encouraging him to move forward. It also highlighted the urgent need to prepare young people for the 21st-century workforce. He’s currently in the process of incorporating his nonprofit organization, which aims to focus on youth workforce development. In addition, he is currently applying to become an Obama scholar.