At Best of Best Review, we celebrate pioneers who don’t just keep pace with change, they define it. That’s why we are proud to honor Sheera Eby with our Best Women AI Innovation in Chicagoland of 2025 award. Based in Chicago, Sheera has become a transformative force in the AI and marketing space, standing out not only for her results but for the systems-level thinking that fuels her approach. Her work proves that true innovation isn’t just about adopting tools, it’s about reimagining how people, processes, and technology work together to drive long-term business impact.

Sheera’s journey has always centered around transformation. With over two decades of experience spanning Fortune 500 companies, disruptive startups, EdTech, FinTech, SaaS, and global nonprofits, her career has been marked by a deep understanding of how to turn complexity into clarity. In the past 18 months, she has focused her energy on AI transformation, working with companies to not just implement AI, but to design entire systems that allow AI to actually work. She approaches AI the way a top strategist approaches an enterprise shift: holistically, deliberately, and with measurable outcomes.

This perspective is rooted in a fundamental truth: most companies approach AI the wrong way. As Sheera explains, “AI isn’t just automation. It’s a business system. You can’t drop AI into chaos and expect clarity.” Her systems-based thinking is a direct response to a troubling trend highlighted by a recent MIT report, which found that 95% of AI pilots fail to deliver business ROI. The failure, as Sheera often points out, isn’t the technology, it’s the lack of organizational readiness, poor data foundations, missing processes, and insufficient training. She’s made it her mission to help organizations avoid those pitfalls.

Her results speak for themselves. Sheera recently reengineered a global campaign asset and content production process, eliminating 40% of the steps and dramatically increasing the team’s output capacity. In other roles, she has delivered a 20% increase in return on ad spend during a declining market, a 500% ROAS (Return on Ad Spend) on B2C eCommerce campaigns, and a 15% increase in MQLs (Marketing Qualified Leads) for enterprise SaaS through a full-funnel B2B strategy. She’s led global go-to-market initiatives that generated over $8 million in SaaS pipeline, proving that her strategies don’t just look good on paper, they deliver real-world impact.

What truly sets Sheera apart is her ability to combine executive-level strategy with hands-on leadership. She doesn’t just advise on AI or digital transformation, she builds the teams, the SOPs, the attribution models, and the behavioral insights that make transformation sustainable. Her work is grounded in data and analytics but fueled by a deep understanding of human behavior and team dynamics. She has a strong belief that organizations need to pair AI tools with structured processes and intentional people development in order to succeed. As she puts it, “If you don’t train your people and redesign your processes, AI won’t scale. It’s that simple.”

Sheera’s influence stretches far beyond Chicago, but her roots in the region reflect the qualities that define Chicagoland business leadership, resilience, innovation, and a commitment to results. Her thought leadership on AI and digital transformation, which she regularly shares via LinkedIn and speaking engagements, has helped countless leaders rethink how they approach growth and modernization. She isn’t interested in buzzwords or surface-level change; she’s focused on building intelligent systems that last.

At Best of Best Review, we evaluated Sheera on several criteria, including demonstrated expertise in AI integration, marketing innovation, quantifiable business outcomes, strategic foresight, organizational transformation, and leadership across industries. She exceeded expectations in every category. Her ability to bridge high-level business goals with on-the-ground implementation makes her a rare and invaluable asset to the companies she partners with.

As the recipient of the Best Women AI Innovation in Chicagoland of 2025, Sheera Eby represents what’s possible when innovation is treated not as a project, but as a mindset. Her systems-first approach to AI adoption is shaping how businesses grow in a fast-changing world. She’s not just helping companies adapt, she’s helping them lead.

To learn more about Sheera’s work, visit sheeraeby.com or connect with her on LinkedIn.