Past Speaking

Speaking, Media
& Thought Leadership

I have spent years speaking publicly about digital transformation, workforce readiness, employee experience, AI adoption, citizen development, leadership, and the human side of change. This page brings together selected podcasts, webinars, conferences, interviews, articles, and public conversations that show the arc of my work.

The Corporate Chapter

Where execution met scale.

For three decades, Shaelyn was the person business units called when digital transformation had to actually work, not just look good in a slide deck. As Senior Vice President and Head of Global Digital Workplace Strategy at a Fortune 500 international financial institution, she led Microsoft 365 and generative AI rollouts across 20 countries, managed a $25M budget, and built the learning and adoption systems that made change stick.

Forty percent adoption increases. A 1,000-person peer learning community. The firm's first generative AI rollout in a regulated environment. Not hypothetical results. Real, tangible outcomes.

Enterprise By Design: Re-architecting Culture in the Age of AI, The Athena Project Founders Salon, November 2025
Enterprise By Design: Re-Architecting Culture in the Age of AI  ·  The Athena Project, Inaugural Founders' Salon  ·  November 2025

The Moment That Changed Everything

Where truth became a gift.

At a large-scale digital transformation industry forum, Shaelyn stood up and told the truth: the bureaucratic red tape, the emotional resistance, the late nights and long weekends, words that resonated amongst her peers in attendance.

Afterward, leaders from companies across the industry came up and said the same thing: that felt like my story. That moment confirmed what she already suspected. Her real gift isn't just execution. It's making people feel seen in the middle of the hardest work of their careers. Coaching, motivating, and inspiring people by building trust is one of her largest strengths.

In Her Own Words

"Shaelyn Otikor-Miller has done the work most organizations only talk about. These are the conversations, stages, publications, and forums where she's said it out loud: the truth about digital transformation, AI adoption, and what it actually takes to bring people through change."

Conferences & Speaking

"Enterprise By Design: Re-architecting Culture in the Age of AI" The Athena Project: Inaugural Founders' Salon  ·  November 2025
"Navigating Risk & Building Resilience in an AI-Powered World" Ex3Labs: AI April  ·  2024
"Elevating Employee Experience Through Technology" Future of Work USA  ·  2023
"Executing on Digital Strategy in a Multigenerational Workforce" World Disrupt Forum Chicago  ·  2019
"Rise Up: Conversations that Inspire, Actions that Make Change" Chicago Women in Technology Conference  ·  2019
"Advancing Potential" Chicago Financial Women's Alliance  ·  2018
"Letters to My Younger Self" University of Chicago: Booth Women's Connect Conference  ·  2018

Podcasts & Webinars

"Shaelyn Otikor-Miller on Dynamics Copilot Rollout" Three Dots: Reworked TV  ·  December 2024
"Matching the Employee Experience to the Customer Experience" FirstUp: Cruising Altitude  ·  April 2024
"The Power of Client Collaboration" Ex3 Labs: Unlocking Innovation Podcast  ·  May 2019
"Managing Imposter Syndrome" I Choose The Ladder  ·  December 2018

Ready to add your event to this list?

Book Shaelyn for your next event.

Speaking engagements, panels, webinars, podcasts, and workshops. Let's start a conversation.

Get in Touch