Being Intrepid: Navigating the Future of Learning with Sam Herring

In this DevLearn Unwrapped episode of Being Intrepid, Sam Herring sits down with Josh Cavalier, Founder and CEO of JoshCavalier.ai and author of Applying AI in Learning and Development: From Platforms to Performance. Josh shares how his diverse background in art, science, and technology prepared him for the rapid rise of generative AI, and why he believes L&D roles are shifting toward what he calls the “Human Machine Performance Analyst.” 

Listeners will hear practical advice on getting started with genAI for learning professionals, the importance of finding a community to support your professional development, and preparing for a future where audio-based coaching and bi-directional learning experiences become mainstream. 

In this episode, you will learn: 

• How the role of “Human Machine Performance Analyst” reframes the profession 
• How to navigate fear and change through community 
• Why audio may be the most underrated generative AI capability 

Connect with Josh: https://www.linkedin.com/in/joshcavalier/  

Order Josh’s book here: https://www.amazon.com/dp/1960231529/ref=cm_sw_r_ffobk_cp_ud_dp_0Y138BYGSJDHX9RZY145 

Connect with Sam: https://www.linkedin.com/in/sam-herring-5944b/ 
 
Catch more Being Intrepid Podcast episodes at https://www.intrepidlearning.com/category/podcasts/ 

Healthcare is complex and getting more digital every day. How do you prepare a frontline workforce for that reality while staying focused on human connection and business impact? 

In this episode of Being Intrepid, Sam Herring sits down with Christy Pletcher, Vice President of Learning & Development at UnitedHealthcare, to explore how her team is reshaping learning in a high-stakes, highly regulated environment. Christy shares how UHC is striving to make the healthcare experience feel more like retail, upskilling advocates for tougher calls, and using AI to coach at scale and cut weeks from training. 

You will learn: 

• Why being both a business and L&D expert matters 
• How UnitedHealthcare is driving digital adoption and self-service 
• The skills frontline advocates need to successfully serve members 
• How “Drive to Digital” and academies support ongoing upskilling 
• Where AI coaching delivers real savings and better experiences 

Connect with Christy: https://www.linkedin.com/in/christy-pletcher-228a7919/ 

Connect with Sam: https://www.linkedin.com/in/sam-herring-5944b/ 

Listen to more episodes: https://www.intrepidlearning.com/category/podcasts/ 

How do leaders actually execute on strategy in a volatile world? They start by taking an honest assessment of their life experiences and recognize how they show up at work. They get curious about their teammates’ life experiences. And they have the courage to help the team talk openly about the patterns and hidden rules on their teams that may hold them back. 

In this episode, Janet McDonald, CEO of Onsite, and Carlos Martinez, Lead Clinician at Onsite, join Sam to unpack human-centered leadership. You’ll experience a brief grounding practice, a practical “above/below the line” tool, and how clinical insight meets business execution to help teams say the unsaid, faster. 

What you’ll learn: 

• Why emotions affect execution more than the best laid plans 
• How vulnerability increases trust and alignment 
• A simple tool to check the urge to “be right” in real time 
• Ways to sustain change back at work with ongoing practice 
• When digital helps — and when human connection is essential 

Connect & Resources: 
Onsite: https://experienceonsite.com/ Onsite 
Onsite on LinkedIn

Connect with Sam

Listen to more episodes: https://www.intrepidlearning.com/category/podcasts/ 

How do you turn learning into Cisco’s innovation engine? 
 
Cisco Chief Learning Officer Marci Paino joins host Sam Herring to share how her team anchors learning to business strategy, builds AI skills for the everyday worker, and scales quality through continuous feedback. From the global AI Workforce Consortium to Cisco’s new “Edge Up” learning experience, Marci offers a practical blueprint for L&D leaders navigating the AI era. 

You’ll learn: 

• How guiding principles drive experimentation and durable growth 
• The data behind AI’s impact on technology roles across G7 economies 
• Where AI upskilling gaps are and how to close them 
• How “minimal lovable products” accelerate learning quality 

Guest: Marci Paino, Chief Learning Officer, Cisco 
Connect with Marci: https://www.linkedin.com/in/marcipaino/
Connect with Sam: https://www.linkedin.com/in/sam-herring-5944b/
 

Listen to more episodes: https://www.intrepidlearning.com/category/podcasts/ 

The L&D market is bigger and louder than ever – and it’s never been more challenging to navigate as a learning leader. In this candid conversation, RedThread Research Co-Founder and Principal Analyst Dani Johnson maps what’s changing and what leaders should do next. From the post-pandemic drop in L&D influence to the real promise of GenAI, Dani offers practical direction and a sharper definition of the learning leader’s true remit: ensure a skilled workforce. 

You’ll learn how to balance in-the-flow support with deep skill building, the importance of focusing on building effective systems not just individual interventions, and why focusing on the “unsexy” data genAI can harvest and analyze is most important. 

What we cover: 

• Why L&D influence halved in recent years and how to rebuild it 
• Learning portfolio management: efficiency vs depth 
• High-impact “unsexy” AI use cases 
• Defining L&D’s remit around skills 

About Dani Johnson: RedThread Research – About Us 
Explore RedThread’s work: RedThread Research – Research & Data 
 

Catch more Being Intrepid episodes: https://www.intrepidlearning.com/category/podcasts/ 

Professional learning is shifting fast. Simplicity, integration, and trust now define great experiences for customers, partners, and credentialed professionals. 

In this episode, host Sam Herring talks with Corri McQuaid, Senior Manager of Business Development, Professional Learning and Enterprise at VitalSource, about delivering secure, scalable content and applying learning science in the flow of work. Corri explains the power of the Doer Effect, a learning science principle, and how Bookshelf+ provides learners an AI-powered study partner within the trusted platform of Bookshelf while protecting publisher IP. 

You’ll learn: 

• The Doer Effect and why practice beats passive reading 
• What “stupid simple” looks like post-COVID 
• How Bookshelf+ supports secure, AI-enhanced study 
• Business model flexibility for internal and external use 

Learn more about VitalSource: https://vitalsource.com 
Connect with Corri on LinkedIn: https://www.linkedin.com/in/corrimcquaid 
 

Catch more Being Intrepid episodes: https://www.intrepidlearning.com/category/podcasts/ 

This special crossover episode of Being Intrepid and SBI, The Growth Advisory brings together Sam Herring (Intrepid by VitalSource) and Ray Makela (SBI Growth Advisory) to explore how AI is reshaping sales, enablement, and learning.

They swap insights on how:

• AI is changing sales coaching and buyer engagement
• Hyper-personalized learning is transforming collaborative cohorts
• Sales managers and L&D leaders can leverage AI-driven insights
• Teams can balance automation with the human side oftraining

If you want to understand how AI is revolutionizing the way we train, coach, and sell, this episode is a must-listen for sales leaders, enablement pros, and learning innovators.

Discover more conversations at the intersection of sales, learning, and AI:

Being Intrepid – Learning & AI Innovation: https://www.intrepidlearning.com/category/podcasts/

SBI, The Growth Advisory – Sales & Growth Strategy: https://sbigrowth.com/value-creation-podcast

Follow Being Intrepid for more conversations with innovators in learning and leadership.

Brian Hackett didn’t set out to start a movement—he just needed advice. That simple ask turned into The Learning Forum and CLO Lift: two platforms where learning leaders rewrite the future of work, one challenge at a time. 

In this episode of Being Intrepid, Sam Herring interviews Brian on: 

• His unexpected path from fired to founder 
• The “big lie” of AI productivity 
• Why the CLO title may be fading, but its purpose is more critical than ever 
• How L&D leaders are building thought leadership and culture, together 
• Tips for aligning with strategy, AI officers, and the business 

This is an episode for anyone who leads learning, or wants to. 

Follow Being Intrepid for more conversations with innovators in learning and leadership. 

In this episode of Being Intrepid, host Sam Herring sits down with Julian Malnak, Senior Director of Leadership Development at GEICO. Hear how Julian is helping lead GEICO’s reinvention into a tech-first, customer-centric company. 

Julian shares strategies for aligning leaders at scale, building culture during massive change, and implementing High-Performance Learning Journeys. They explore practical approaches like toolkits, coaching, and the role of AI in the future of L&D. 

If you're a learning leader looking to deliver impact at scale, this episode is for you. 

Follow Being Intrepid for more conversations with innovators in learning and leadership. 

How can learning leaders prepare their organizations for the AI revolution? 

In this episode of Being Intrepid, Sam Herring talks with Tal Goldhamer, founder of Find The Tailwind and former CLO at EY, about practical strategies for AI upskilling, why mindset is key, and how formal learning itself will evolve. 

What you'll learn: 

• How to design practical AI upskilling strategies for your workforce 
• Why mindset is the biggest barrier (and opportunity) in AI adoption 
• The surprising decline of formal learning in an AI-enabled world 
• The enduring human skills professionals will need most 
• How CLOs can secure a strategic seat at the table during AI transformation 

Tal shares candid advice for CLOs looking to stay relevant and lead boldly in an AI-driven world. 

Subscribe for more bold conversations on the future of learning. 

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