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" i...

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...

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 measu...

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 th...

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, showin...

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 m...

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 en...

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 de...

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,...

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...

The financial conversation is, in some circles, taboo. In others, stressful. In many, ego driven and emotional. But really, it's all data. It's numbers and options and decisions to be made. That's why I'm so excited to welcome our guest today, Elke Rubach, Founder and President of Rubach Wealth. Elke is an expert in removing emotions, tuning out all the noise, and normalizing money conversations....

In this episode of Humanize Automation, I sit down with franchise expert and business matchmaker Lance Graulich to break down the often-misunderstood world of franchising. Whether you're franchise-curious or just automation-obsessed, this episode unpacks how systems, data, and human insight intersect to create scalable business success. We dive into the power of using assessments to align leadersh...

There are millions of ways you can use ChatGPT to get more organized, and some of them may be found outside the box. This week, I want to talk about something unconventional I recently did with ChatGPT that made me happy. Welcome back to another mini episode of Humanize Automation.  

What happens when marketing doesn't speak the same language as sales? Confusion, missed opportunities, and a whole lot of wasted content. In this week's episode of Humanize Automation, I sit down with B2B marketing expert and author Pam Didner to explore the evolving intersection of sales, marketing, and AI. Pam breaks down real-world ways to use tools like ChatGPT to improve workflows, personaliz...

You don't need a PhD, a tech background, or a venture capital check to win with AI. You do need vision and a bit of courage. With no engineering background, Shashank Shekhar built one of the first generative AI platforms for mortgage professionals, dramatically increasing productivity and transforming the way his team works.   In this episode, we explore: Why now is the time to build—even if you'r...

This week, I am thrilled to be joined by Dr. Kathryn Doornbos, Director of Clinical Partnerships at Realyze Intelligence, to explore how artificial intelligence is revolutionizing cancer research and treatment. Learn how AI tools are being used to sift through massive amounts of patient data, identify clinical trial candidates, and even prevent unnecessary procedures. This is a hopeful, practical,...

The conversation we're going to have today may be one that makes some of you uncomfortable, and that's because today's guest is an expert in helping people deliver feedback in a way that actually gets results.    Jeff Hancher is a leadership expert, executive coach, and keynote speaker dedicated to helping individuals and organizations reach their fullest potential. Jeff began his corporate journe...

What's an API? And why does it matter to your business? In this mini episode of Humanize Automation, I walk through an example of a business utilizing the power of automation to enhance their customer experience. Whether you're selling a product, offering a service, or onboarding clients, this episode is for you!   https://www.youtube.com/@dynamicjill https://www.linkedin.com/in/dynamicjill/ https...

This week, I'm joined by world-renowned cybersecurity expert Dr. Eric Cole to explore the rapidly evolving intersection of cybersecurity and artificial intelligence. From his beginnings as a professional hacker at the CIA to advising presidents and leading Secure Anchor, Dr. Eric brings decades of experience to the pressing questions of our digital age.   From protecting your personal data to unde...

In this episode of Humanize Automation, I'm joined by Mike McGloin, founder and CEO of Fuze, to talk about how automation and authenticity can coexist—especially on LinkedIn.   Mike unpacks how founders and B2B leaders can ditch robotic outreach and use smart tech to build real relationships. From crafting a LinkedIn presence that actually sparks conversation, to building a lean, efficient tech st...

Whether it was in high school or college, most of us have met with a guidance counselor at some point in time. Some of us have had great experiences, and some of us have had not so great experiences. This week, I'm joined by AI expert and founder of Advisor. AI, Arjun Arora, to learn about the work his company is doing to help both students and advisors. By aligning coursework with career goals an...

If you've ever been stressed about having conversations around money, you're going to want to tune in today. How we deal with our money is actually way more complex than it may seem on the surface. That's why I've brought on financial expert, author, podcast host, and coach, Lisa Chastain to the podcast today. Lisa empowers women to shed the burden of financial shame, unlock their potential, and c...

AI outputs are predicated on human inputs. When it comes to humanizing automation, one way you can take advantage of the tools and technologies that exist today is by having your data in order. This minisode is all about data fluidity, and I'm going to show you a framework that will help you zoom out and conceptualize how you might want your data in order. Let's get started!   Connect with Jill: Y...

Jeff Wright is the CEO and President of Agent Sales Group, growing his business from a one-man operation to a network of 20,000+ agents with life insurance sales of over $25 million of new annual premium every year. His experience extends far beyond the insurance world, as he consults salespeople of all backgrounds, as well as professionals in the legal and medical community. Jeff helps managers,...

Dr. Agnis Stibe, a visionary in sustainable living and community wellbeing, has dedicated his career to advancing the human experience. Renowned globally for his expertise in neuroscience, sustainable design, and artificial intelligence, he leads the charge in research and theory advancement. This week, I am so excited to sit down with Dr. Stibe and dive into behavioral change, achieving hyper-per...