Keith Oelrich, CEO of the Year (2023) by the Portland Business Journal, boasts a distinguished career characterized by exceptional leadership and innovation in business and technology. Known for his remarkable ability to lead and transform organizations, Keith has successfully managed teams of over 500 employees and held executive positions in billion-dollar companies. His career is marked by his expertise in managing hyper-growth, startups, turnarounds, and venture or PE-backed companies. With 17 M&A transactions under his belt, Keith has adeptly navigated 9 acquisitions and 8 sales, demonstrating his strategic acumen and proficiency in corporate growth and restructuring.
Keith’s impact on digital education is profound, having delivered programs to tens of thousands of schools and millions of students and families. As a prominent industry advocate, he has engaged with U.S. Presidential candidates, Secretaries of Education, Governors, Congress members, state legislators, private investors, and numerous families to champion the cause of digital learning. His tenure as CEO of Learning.com exemplifies his transformative leadership, where he orchestrated a financial turnaround, rebuilt the leadership team, and fostered a highly effective culture. Under his guidance, Learning.com achieved the best ARR growth in its history and was recognized as a Top Workplace in Oregon for seven consecutive years.
Before Learning.com, Keith co-founded Ignite Education Group, focusing on creating online career academies, which he successfully sold to Learning.com. At Insight Schools, he pioneered the nation’s first multi-state network of full-time, statewide online public high schools, growing the organization to over 550 employees and generating $50M+ in annual revenue within five years. His strategic initiatives have consistently driven performance improvements and innovative practices in the online education sector.
Keith’s leadership extends to significant roles at KC Distance Learning, Apex Learning, and SpeedyClick, where he demonstrated his ability to drive rapid growth and profitability. His academic credentials include an MBA with Distinction from Cornell University and a BA in Economics from the University of Washington. Recognized for his outstanding contributions to the K-12 online learning industry, Keith continues to inspire through his visionary leadership and unwavering commitment to educational innovation.
With a rich background that spans international operations and business development, Keith’s global perspective and strategic insights have made him a respected figure in the business community. His involvement in various advisory boards and community initiatives reflects his dedication to fostering growth and excellence both within and beyond his professional endeavors.
Character: Keith Oelrich exemplifies integrity, resilience, and innovative leadership in transforming organizations and driving educational advancements.
Knowledge: With extensive expertise in digital education, business strategy, and leadership, Keith has a proven track record of successfully leading startups, turnarounds, and hyper-growth companies.
Strategic: Keith strategically guides organizations through complex transformations, leveraging his skills in mergers and acquisitions, revenue growth, and cultural development to achieve remarkable business outcomes.
Communication: Keith excels in effectively communicating complex ideas, fostering collaboration, and engaging with diverse stakeholders to advocate for and implement innovative educational solutions.
