Humanize Automation

What if the biggest mistake leaders are making with AI... is how they're thinking about it? In this episode, Dr. Jill Schiefelbein sits down with Brittany Greenfield—cybersecurity founder, consultant, and 40 Under 40 honoree—to unpack why most AI strategies are failing before they even begin. Drawing from decades in enterprise tech, Brittany explains why organizations are chasing "parlor tricks" instead of building real, human-centered solutions—and what it actually takes to make AI work. Together, they challenge the hype, break down the fear, and reframe AI not as a replacement—but as a partner that amplifies what humans do best.

Key takeaways:

• Why starting with people—not tools—is the foundation of successful AI adoption
• The danger of "performative AI" and how it's quietly holding teams back
• How small, strategic steps (not big leaps) lead to real innovation and impact

If you've ever felt behind, overwhelmed, or skeptical about AI—this conversation will ground you, reframe your thinking, and show you a smarter path forward. Because the future of AI isn't about moving faster—it's about thinking better.

Connect with Brittany Greenfield: LinkedIn: https://www.linkedin.com/in/brittanygreenfield Website: https://brittanygreenfield.com Connect with Dr. Jill Schiefelbein: LinkedIn: https://www.linkedin.com/in/jillschiefelbein Website: https://www.drjill.com

This week, I'm joined by Jeremy David, CEO and Founder of ConvoGPT, to explore how automation is transforming the sales funnel—without removing the human element. From lead generation to conversion, we explore how AI can take on repetitive tasks so sales teams can focus on what truly drives results: relationships.

We dive into the realities of AI implementation, the misconceptions around "instant results," and why the future belongs to professionals who know how to leverage technology while thinking critically and connecting authentically.

Connect with Jeremy:

Website: convogpt.ai

Instagram: @convogpt_ai

Instagram: @mr.jd319

Welcome back to Humanize Automation! This week, I'm joined by Jonathan Aberman, CEO and Co-Founder of Hupside, to explore the concept of Original Intelligence, the measurable human contribution that creates differentiation in an AI-driven world.

As organizations rush to deploy AI tools, Jonathan challenges the idea that automation alone creates value. Instead, he shares how understanding and measuring originality can help leaders better align people, tools, and outcomes.

We discuss why one-size-fits-all AI training falls short, how AI can act as an accelerant for creativity rather than a replacement for it, and why human-centered strategy matters more than ever.

Connect with Jonathan:

LinkedIn: Jonathan Aberman

Website: hupside.com

How do we teach kids to use AI before it starts shaping how they think, learn, and see the world?

This week, I'm joined by Jeff Riley, former Massachusetts Commissioner of Education and current Executive Director of Day of AI, an organization working at the national level to help students, educators, and families understand AI in safe, ethical, and productive ways.

From AI literacy and critical thinking to bias, misinformation, and long-term cognitive impact, this conversation explores what children actually need to know about AI. Not just how to use it, but how to evaluate it. We unpack why "trust but verify" matters, how automation can support deeper learning instead of shortcut thinking, and what it looks like to prepare the next generation for a future where AI is everywhere.

Connect with Jeff:

Website: ​​dayofai.org

LinkedIn: Jeffrey C. Riley

You've heard the terms UI and UX, but what do they really mean when AI is in the mix? This week, I sit down with Nick Cawthon, Principal at Gauge, to explore how human behavior and design intersect with technology, and why trust might be the most important factor in whether people actually use what we build.

Nick brings stories from the early days of the internet to today's AI-driven tools, showing how design isn't just about making things look good. It's about creating experiences that feel intuitive, reliable, and human. This isn't a conversation about technology for technology's sake. It's about making automation work for people.

Connect with Nick:

LinkedIn: Nick Cawthon

Website: gauge.io

AI may be powering more of our customer interactions than ever before, but when the technology is built without empathy, it misses the mark, especially with the world's most influential consumer: women. By 2028, women will control 75% of discretionary spending, yet most AI-driven experiences are still designed from a male perspective. In this episode, I sit down with Katie Mares to unpack what's missing in today's AI-powered customer experiences and how to bridge the gap between human emotion and machine efficiency.

Connect with Katie:

Website: katiemares.com

Book: CustomHer Experience

Instagram: @katiemares

Would you trust AI to manage your money? For many, the answer is an immediate "no." But what if AI could give you more control, not less? In this episode of Humanize Automation, I sit down with Robert Grzesik, founder and CEO of BotSpot, to explore how AI-powered financial agents are changing the way we invest. From democratizing access to advanced trading strategies to creating safeguards that ensure trust and clarity, Rob shares why the future of finance isn't about replacing humans. It's about empowering them. If you've ever wondered whether AI could truly give you an edge against Wall Street, this is a conversation you don't want to miss.

Connect with Robert:

LinkedIn: Robert Grzesik

BotSpot: botspot.trade

Lumiwealth: lumiwealth.com

In this episode of Humanize Automation, I am joined by Yair Klyman, founder of Klyman Financial, to explore the evolving intersection of AI, behavior, and creativity in the financial services space.

We dive deep into what it really means to personalize financial advising in an age of scale, why adding value starts with understanding people, and how creativity will be the competitive edge that defines the next generation of business leaders.

Connect with Yair:

Website: klymanfinancial.com

Instagram: @klymanfinancial

Podcast: Resilient Riches

What if AI could help you think more clearly, decide more wisely, and live more fully? In this episode of Humanize Automation, I get to sit down with AI pioneer, entrepreneur, and consultant, Manuj Aggarwal, to explore how artificial intelligence can actually enhance our humanity. From personalized education to decision support and self-awareness, we unpack how technology can help us reclaim time, reduce mental load, and connect more meaningfully.

Connect with Manuj:

Website: manujaggarwal.com

LinkedIn: Manuj Aggarwal

Instagram: @manujagro

If you want to hear about what type of AI and automation program can come out of conversations in a dark alley in Cairo and Chipotle forgetting queso, then this is an episode you won't want to miss. You're in for such a treat today, because I am joined by my good friend and fellow adventurer, Ashish Sanghrajka. Ashish is President of Big Five Tours & Expeditions, and in this episode, we dive into everything that they are doing in their new navigator and program to better serve their clients using AI, automation, and keeping humans in the loop.

Connect with Ashish:

Website: bigfive.com

LinkedIn: Ashish Sanghrajka

Podcast: The Sustainable Voice