Heather brings a 35-year track record of creating and scaling nonprofit and for-profit organizations, that have improved the lives of millions of people. Heather is the founder or co-founder of SFWorks, EARN, Hiles Group, Pathbrite, Calbright College, and Imminent Equity. What drives Hiles? The desire to close the opportunity gap and empower people to do their best work. They support self-actualization and evangelize lifelong learning. Hiles continues to help democratize access to learning by serving on the board of directors at Udemy, the world’s largest teaching, and learning marketplace. Hiles is inspired to solve large-scale problems, strives to stay data-driven and intellectually honest while remembering that all organizations are only as good as the people who power them.

During the process, Hiles raised $12m in venture capital and from 2021-2019 was “the” black woman who had raised the most and had the largest exit. Pathbrite is still used by millions of users, and hundreds of colleges and universities. After the sale of Pathbrite, Hiles worked with the Bill & Melinda Gates Foundation where they were able to conduct deep research into AI/ML, VR/AR, and blockchain technologies, and invest in funds and directly into cutting edge education technologies. Hiles realized at Gates that they love landscaping sectors: building investment theses; conducting due diligence; and building the compacity of portfolio companies. As a result, Hiles moved to run Black Ops Venture Funds to increase the amount of venture capital deployed to worthy black-founded startups.

Post business school, Hiles worked at a consulting firm helping scale banks and brokerage firms. Upon sale of that firm Hiles launched an online job training organization (SFWorks) and a fintech (EARN) non-profit organization to build help people build wealth. At SFWorks, Hiles partnered with numerous foundations and realized that there was an unmet need in the field of strategic philanthropy—to help optimize the impact of grant-making. The Hiles Group was launched in 2001. Hiles group served over 100 clients including individuals/families and community, family, private, corporate, and public foundations. As a self-made technologist and advocate of learning technologies, Hiles decided to create one of the most effective learning technologies: digital portfolios. Heather conceptualized and conceived the first cloud-based enterprise portfolio platform. Hiles was able to take an idea from research and wireframes (2021) to building, scaling, and selling the company Pathbrite in 2015.