Shaelyn Otikor-Miller
Digital Transformation & AI Adoption Leader | Connecting Enterprise Strategy to Community Impact | Founder, Beyond Boundaries Without Measures | Speaker | Consultant
Shaelyn Otikor-Miller
Digital Transformation & AI Adoption Leader | Connecting Enterprise Strategy to Community Impact | Founder, Beyond Boundaries Without Measures | Speaker | Consultant
Shaelyn Otikor-Miller accelerates digital and AI transformation through strategic implementation that keeps people at the center of change. With three decades of experience in complex, highly regulated environments, she helps global teams adopt new tools, navigate uncertainty, and deliver measurable results, turning strategic visions into everyday reality.
Proven Execution in Complex Environments
As the former Senior Vice President and Head of Global Digital Workplace Strategy at a Fortune 500 international financial firm, Shaelyn has led multi-year, high-stakes initiatives that reshaped how thousands of employees work. Her leadership spans global platform migrations, Microsoft Dynamics and Microsoft 365 implementations, and the rollout of generative AI tools such as Copilot in one of the world's most regulated industries.
Across these efforts, her focus has been consistent: segmenting learning journeys, mobilizing “everyday innovators” through citizen development programs, and building change strategies that honor both risk and reality. Rather than treating employees as passive recipients of technology, she equips them to become active champions of transformation.
From Boardrooms to Community Rooms
As founder and president of Beyond Boundaries Without Measures (BBWM), Shaelyn brings the same people-centered approach into the community she calls home.
BBWM is a nonprofit that offers free computer, digital, and AI training in a 20-seat computer lab based in South Holland, Illinois, for adults ages 18 and up across South Suburban Cook County. The lab serves new digital learners, working professionals, small business owners, and career changers who want to build computer and AI skills, gain confidence with technology, and unlock better economic opportunities.
Through hands-on computer and AI training, BBWM helps participants use technology to pivot into better roles, earn more, and grow sustainable businesses. In addition to leading the organization, Shaelyn is actively in the classroom: teaching workshops, proctoring skills-based assessments, and piloting new models for inclusive, multi-generational digital learning.
Education & Expertise
Shaelyn received her bachelor's degree from DePaul University and her MBA from the University of Chicago Booth School of Business. She also holds a Diversity & Inclusion Certificate from Cornell University and previously held the Project Management Professional (PMP) certification.
Her combination of strategic business training, hands-on implementation experience, and community-based teaching gives her a rare perspective on what it really takes to move people, from boardrooms to neighborhood computer labs, through digital and AI transformation.