Every growing business reaches a point where spreadsheets, sticky notes, and manual follow-ups stop working. Growth exposes inefficiencies — the question is whether you patch them or systematize them.
In this dynamic panel, industry leaders will explore how automation, workflow systems, and artificial intelligence can help entrepreneurs work more efficiently and scale sustainably.
This session will bridge the gap between technology and real-world business needs—covering implementation strategies, ethical considerations, and policy implications.

Attendees will leave with:
• A clearer understanding of how automation and AI can support daily operations
• Practical examples from small and growing businesses
• Insight into the evolving regulatory landscape
Whether you’re just starting your business or ready to scale, this panel will provide actionable insights for building a smarter, more sustainable business.

Meet Your Panelists

Shermiah Holland

Shermiah Holland is the Chief Information Officer and Co-Founder of EnVue Health, where she leads technical innovation focused on expanding access to quality healthcare and advancing inclusive, patient-centered solutions tailored to individual needs. She is the Founder of Elevar, a strategic advisory and leadership development firm that partners with leaders, founders, and organizations to adopt technology, strengthen leadership capability, and scale sustainable growth.

Through Elevar, Shermiah advises entrepreneurs and executives on business scaling, operational strategy, financial management, and leadership development. Her multidisciplinary background across healthcare, business, and technology has enabled her to deliver transformative solutions to rural healthcare systems and cultivate trusted partnerships within tribal communities across the United States.

Shermiah is an equity stake partner in the Peach Cobbler Factory franchise system, contributing to the brand’s rapid expansion from two locations in 2022 to more than 150 stores nationwide, with over 250 additional locations committed.

As Certified Project Management Professional (PMP), portfolio manager, program director, software developer, and business strategist, Shermiah brings extensive experience building and scaling organizations across industries. She holds a Master of Business Administration (MBA) and Master of Science in Business Analytics (MSBA) from the University of Louisville, followed by Bachelor of Science degrees in Computer Science, Mathematical Economics, and Biology from the University of Kentucky. She also holds Healthcare Management, Cybersecurity, and an AI in Healthcare certification from Cornell University.

Driven by innovation and economic empowerment, Shermiah’s entrepreneurial journey centers on strengthening communities, fostering inclusive growth, and mentoring the next generation of women in technology, business, and STEM leadership.

Jenna Ahern

Jenna Ahern is the Founder and CEO of Guardian Owl Digital and its AI-powered division, GO AI. She partners with leadership teams navigating scale, complexity, and transformation using disciplined digital strategy, analytics, and applied AI.

A 2025 Business First Most Admired CEO honoree, Jenna has advised and supported organizations ranging from founder-led startups to nationally recognized brands including Angel’s Envy, GE, and the Kentucky Derby Museum. Her work has been featured by Forbes, Business Insider, and Fast Company, and recognized with a Best Data-Driven Campaign honor at the Netty Awards.

Known for translating complexity into clarity, Jenna is a frequent speaker at national conferences and universities, including ESPNW, Women in Digital, Women in Tech, and the University of Louisville, where she serves as a part-time AI lecturer in the College of Business. She also hosts The GO AI Podcast, exploring how organizations responsibly integrate AI into real operating environments.

Guardian Owl Digital delivers end-to-end growth architecture spanning web platforms, SEO, paid media, creative production, analytics governance, and AI-enabled marketing agents. The firm is often engaged when the stakes are high, data must be trusted, and leadership teams need a clear line of sight from strategy to execution.

Before founding Guardian Owl, Jenna built her foundation inside three Google Premier Partner agencies and two of the world’s largest automotive search engines, Autotrader and Kelley Blue Book. A former Vice Captain of the Nationally ranked University of Louisville Division I field hockey team, she brings a steady, team-first leadership style shaped by competition, accountability, and long-term thinking.

Carrie Downey

Carrie Downey is the founder of CLARITY CO., a consulting firm that helps businesses work smarter by building better systems. With dual Master’s degrees in Social Work and Public Administration, she began her career as a trauma therapist before following her passion for efficiency and digital strategy.

Since 2014, she’s helped organizations nationwide streamline workflows and boost productivity through monday.com, creating customized solutions that foster both clarity and collaboration. Now based in Lexington, Carrie is a wife of 25 years, mom to two driven daughters, and a leader who believes: “If there’s a will, there’s a way.”