Meet the founder Jessica Arrington (Hall)
After gaining extensive experience through her education at Hollins University—including the Batten Leadership Institute Certification Program and Graduate Studies—Jessica Arrington embodies the core values of creativity, effective self-expression, problem-solving, and critical thinking. Hollins’ emphasis on independent inquiry and the free exchange of ideas has shaped Jessica’s approach to her work, which prioritizes civility, integrity, and concern for others. Committed to social justice and valuing diversity, she embraces Hollins’ motto, “Levavi Oculos,” which has guided her journey in leadership and service across all aspects of her life.
Jessica Arrington is the powerhouse behind On Cloud Arrington Enterprises, a one-stop-shop dedicated to empowering Founders, Owners, C-Suite Executives, Pastors, Directors, and Managers of nonprofits and businesses. With a strategic focus on helping clients break free from their drudgery zone, she addresses pain points without shame, providing tailored strategies, implementation planning, and execution support. Jessica’s approach is rooted in patience, active listening, resourcefulness, and skill-building, making her an invaluable partner in driving success.
As Jessica works with her clients, they quickly notice that “we” organically becomes a part of her language instead of “you.” This shift is intentional and powerful. By using “we,” Jessica fosters a true sense of partnership and collaboration. It reflects her belief that success is a shared journey, not a one-sided transaction. When her clients succeed, they do so together with her—working side by side to strategize, implement, and execute. Jessica understands that her clients don’t need to feel isolated with their challenges, and by saying “we,” she conveys that they’re in it together, working toward common goals.
Her diverse background spans various industries, including Hospitality, Data Management, Marketing, Higher Education, Technology, Community Engagement, Website Design, Social Media, Team Building, Life Skills, DEI (Diversity, Equity, Inclusion, and Accessibility), Human Resources, Talent Acquisition, Lead Generation, and Sales, among others. Jessica’s expertise extends to working with Fortune 500 companies and nonprofit organizations, impacting communities on both global and local scales.
Outside of her professional life, Jessica is dedicated to community service alongside her family. She serves as a Rotarian with the Lynchburg Morning Rotary Club and volunteers through CarePortal with Spirit of Unity Baptist Church, continuing her commitment to leadership and helping others.
On Cloud Arrington Enterprises is here to support you in getting unstuck and reclaiming your time by tackling the challenges you face as a business leader. Jessica’s dynamic, collaborative approach means you no longer need to ask, “Who can I hire for this? How do I do this? When will I have time to do this?”—because she’s got you covered with strategic, hands-on solutions that drive results. “Who can I hire for this? How do I do this? When will I have time to do this?”—because she’s got you covered with strategic, hands-on solutions that drive results.
Jessica Arrington 