What separates organizations that successfully leverage artificial intelligence from those that struggle to realize value?

According to Andrew Brooks, the answer lies in moving beyond generic AI assistants and focusing on purpose-built AI solutions tailored to how a business operates. In this insightful conversation, Andrew shares lessons learned from decades of entrepreneurship building and scaling technology companies, including SMB Live, SmartThings, and now Contextual.

Andrew explains why entrepreneurs must develop deep conviction when pursuing new opportunities and how successful founders identify market gaps before the broader market can fully define them. He reflects on the entrepreneurial mindset required to build enduring businesses and the importance of maintaining relentless forward progress, even during periods of uncertainty.

Sara and Andrew dive deeply into the rapidly evolving AI landscape. Andrew introduces the philosophy behind "own your AI," arguing that AI should become a core strategic asset rather than a rented feature inside a software platform. He explains why AI is emerging as a new business layer alongside people, process, and technology, and how organizations can create defensible competitive advantages through customized AI solutions.

Andrew also shares fascinating insights from his experience completing seven marathons on seven continents in seven days. He discusses how endurance athletics reinforced a leadership principle that continues to guide his entrepreneurial journey: relentless forward progress.

Sara and Andrew emphasize that the pace of AI innovation will not slow down. Leaders who wait for stability before acting risk being overtaken by faster-moving competitors. Instead, organizations should begin experimenting, learning, and building internal capabilities today.

This episode is essential listening for CEOs, founders, executives, private equity leaders, and transformational thinkers seeking to leverage AI for sustainable competitive advantage and long-term business growth.

Join Sara and Andrew for a compelling conversation about leadership, entrepreneurship, innovation, AI transformation, and the future of work.

Key Moments:

00:02:15 | From Chemistry to Technology Entrepreneurship

00:05:40 | The Entrepreneurial Drive Behind Serial Success

00:06:46 | Recognizing Market Gaps Before Everyone Else

00:09:06 | Why CEOs Need to "Own Their AI"

00:11:52 | Moving Beyond AI Automation to Business Transformation

00:13:33 | Inside Solution AI and AI Building AI

00:18:02 | The Real Barriers to Enterprise AI Adoption

00:22:23 | The Rise of the AI Transformation Partner

00:26:09 | What Separates AI Ready CEOs from Everyone Else

00:27:44 | Human Adaptation in the Age of Rapid AI Change

00:32:18 | Which Jobs Are Most Vulnerable to AI?

00:36:34 | Endurance Athletics, Leadership, and Relentless Forward Progress

00:40:36 | Knowing When to Stay the Course as a Founder

00:44:31 | What Every CEO Must Do Differently About AI Now

Resources mentioned in this episode:

About Andrew Brooks:

Andrew Brooks is a serial entrepreneur, technology founder, author, and CEO of Contextual. He has founded and scaled multiple innovative companies, including SmartThings, which was acquired by Samsung, and SMBLive, which was acquired by ReachLocal. He has also helped create and grow ventures, including Mural and Mindstamp.

A Princeton University chemistry graduate, Andrew is passionate about building businesses that leverage emerging technologies to solve complex challenges. Outside of work, he is an accomplished ultra-endurance athlete, having completed seven marathons on seven continents in seven days, multiple Ironman races, and 100-mile ultramarathons.

Andrew is also a proud father and the father of an author, bringing the same spirit of curiosity, resilience, and relentless forward progress to both his professional and personal life.

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What does it take to build category-defining companies, lead through massive technological change, and still maintain perspective on what matters most?

In this inspiring episode of Transformational Thinkers, Sara Sheehan sits down with Maria Colacurcio, CEO of Syndio and co-founder of Smartsheet, to discuss the intersection of leadership, AI,  pay equity, and personal growth. Maria shares how her experiences as an entrepreneur, executive, athlete, wife, and mother have shaped her belief that leaders must develop change agility to succeed in today's rapidly evolving business environment.

Maria reflects on her experience launching Smartsheet and the lessons learned from building a company amid economic uncertainty, product pivots, and the challenges of scaling a startup from an idea to a public company. She explains why some of the hardest moments often become the most meaningful chapters in an entrepreneur’s journey and why learning to do hard things remains one of the most valuable leadership skills.

They discuss Syndio and its mission to transform compensation management. Maria discusses the company’s evolution from a pay equity platform to a comprehensive pay decision-intelligence solution. She explains how increasing pay-transparency regulations, global compliance requirements, and advancements in artificial intelligence have created an opportunity to rethink how organizations make compensation decisions.

Sara and Maria also explore what it takes to create entirely new market categories, build momentum around innovation, and recognize when organizations need to pause, validate strategy, and prepare for their next stage of growth. Maria shares why leadership teams must evolve alongside the business and how bringing in specialized expertise can accelerate transformation when the timing is right.

Beyond business, Maria offers a fascinating look into her success as a competitive HYROX athlete. She explains how training for world-class competition has strengthened her resilience, sharpened her mindset, and reinforced lessons that apply directly to entrepreneurship and leadership. Her perspective on pushing beyond perceived limitations provides powerful takeaways for anyone pursuing ambitious goals.

Whether you are leading organizational change, navigating AI adoption, building a high-growth company, or striving to become a stronger or better leader, this episode delivers practical insights and inspiration for embracing transformation with confidence.

Tune in to discover how change agility, responsible AI, and intentional leadership can help organizations create fairer workplaces and achieve extraordinary outcomes. 

Key Moments:

00:00:01 | Meet Maria Colacurcio

00:00:25 | Beyond the LinkedIn Profile

00:01:55 | Recognition Beyond Gender

00:04:20 | Lessons from Building Smartsheet

00:08:16 | Why Doing Hard Things Matters

00:09:04 | The Evolution of Syndio's Mission

00:13:56 | Revolutionizing Compensation Decisions

00:15:07 | Becoming a First-Time CEO

00:17:52 | The Power of Change Agility

00:18:32 | Building an Entirely New Category

00:22:21 | Earning Trust with Sensitive Data

00:26:11 | When AI Became the Future of Syndio

00:31:25 | Scaling Trust Across 10 Million Employees

00:34:45 | Building the Next Leadership Team

00:37:37 | HYROX Championships, Resilience, and Leadership

00:43:06 | The Future of Decision Intelligence for Pay

00:46:05 | Final Thoughts and Looking Ahead

Resources mentioned in this episode:

About Maria Colacurcio:

Maria Colacurcio is reshaping how enterprises govern their largest and most consequential investment: how they pay their people. As CEO of Syndio, she leads the company that defined the market for pay equity software and is now pioneering Decision Intelligence for Pay. Under her leadership, Syndio partners with global brands including Walmart, Microsoft, and Salesforce to make every pay decision compliant, optimized, and aligned with business strategy. 

Maria previously co-founded Smartsheet, which went public in 2018. She has built her career at the intersection of technology, policy, and purpose-driven leadership, earning recognition as one of the 100 most exceptional entrepreneurs by Goldman Sachs Builders + Innovators Summit.

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In this episode of Transformational Thinkers, Sara Sheehan welcomes Jeff Revilla, founder of the Infinite-Seat Theater concept and longtime podcast creator, to discuss how live podcasting is creating a new path forward for independent creators.

Jeff explains that traditional podcast monetization through advertising often fails independent podcasters because only a small percentage of shows reach the download thresholds required for ad revenue. Instead of chasing CPM-based advertising models, Jeff encourages creators to focus on building real-world audience experiences that generate revenue immediately through ticket sales, merchandise, sponsorships, and live engagement.

Inspired by the “Moneyball” philosophy, Jeff shares how he bootstrapped a podcast theater model designed specifically for small and mid-level podcasters. His concept transforms affordable local venues into intimate podcast performance spaces that can simultaneously reach in-person audiences and unlimited virtual attendees through hybrid live-streaming.

Sara and Jeff explore how Infinite-Seat Theaters work, including how creators can start with small audiences and still create financially sustainable events. Jeff explains that even a live audience of 10 to 20 people can dramatically outperform traditional podcast downloads while helping creators build audience loyalty and long-term community engagement.

Throughout the episode, Jeff shares examples of creators leveraging live podcasting across multiple genres, including sports, paranormal storytelling, trivia, politics, motherhood content, parenting, and educational programming. Sara highlights how the model creates credibility for creators by elevating podcasts from home studio productions into live public experiences.

Jeff also breaks down the layered monetization strategies available to podcasters through live events, including:

• Ticket sales • VIP experiences • Merchandise sales • Sponsorship placements • BYOB ticket upgrades • Audience participation experiences • Hybrid virtual attendance

Sara and Jeff discuss the growing consumer demand for authentic in-person experiences in response to increasingly digital and AI-driven environments. Jeff explains why he believes small live podcast venues will become a critical stepping stone for creators seeking to grow into larger conferences, theaters, and touring opportunities.

The conversation also explores entrepreneurship and leadership transformation. Jeff candidly shares the emotional highs and lows of building a new business model, the importance of maintaining resilience through uncertainty, and why bootstrapping and resourcefulness helped him bring his vision to life.

As the episode closes, Jeff shares his long-term vision for a nationwide network of podcast theaters that allow creators to tour cities the same way comedians and musicians do today. He encourages creators to embrace their unique voices, stop waiting for permission, and build meaningful experiences that create lasting impact for their audiences.

This episode offers powerful insights for creators, entrepreneurs, CEOs, marketers, and transformational thinkers looking to understand the future of podcasting, creator monetization, audience engagement, and experiential business models.

Key Moments:

00:00 Introduction to Live Podcasting and Infinite-Seat Theaters

01:15 Why Traditional Podcast Monetization Fails Most Creators

03:10 The Birth of the Infinite-Seat Theater Concept

05:13 How Infinite-Seat Theaters Change Podcast Economics

07:27 Why Even Small Live Audiences Create Big Value

09:08 Hybrid Podcasting and Virtual Audience Engagement

10:26 Early Reactions to the Infinite-Seat Theater Model

11:52 The Different Types of Podcasts Thriving in Live Events

13:39 How Live Podcasting Deepens Audience Relationships

15:18 Why Live Podcasting Elevates Creator Credibility

17:04 Growing a Podcast Theater Through Community and Meetups

22:28 Podcast Monetization Strategies Beyond Advertising

28:09 Why In-Person Experiences Are Making a Comeback

34:10 Entrepreneurship, Leadership, and Emotional Resilience

38:10 The Future of Podcast Theater Networks and Creator Touring

40:53 Interactive Audience Engagement and the Future of Live Podcasting

43:17 The Power of Authenticity and Finding Your Voice

About Jeff Revilla:

Jeff Revilla is an entrepreneur, podcast creator, and founder of the Infinite-Seat Theater concept. He is the leading voice in live podcasting, helping creators turn their shows into profitable, audience-driven stage experiences from day one. Through his podcast theater model, Jeff is pioneering a new framework for scalable live podcasting and creator-led entertainment experiences.

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In this episode of Transformational Thinkers, Sara Sheehan interviews Alan McLaren, a leadership strategist specializing in how executive presence and behavioral signals shape organizational outcomes. Alan introduces the concept of Leadership Signal Architecture, a framework designed to help leaders understand how others experience their leadership, and how that experience directly impacts trust and business scalability.

At the core of the conversation is a critical insight: trust is the foundation of all business performance. Even with a strong strategy, advanced technology, and talented teams, organizations struggle when leaders send inconsistent signals. Subtle misalignments in signal architecture create hesitation and lead to costly inefficiencies, including delayed decisions and “meetings after the meeting.”

Alan outlines five key components that define a leader’s signal:

He emphasizes the “invisible variable” in every interaction: how others feel in a leader’s presence. This emotional and subconscious response determines whether teams align, resist, disengage, or leave entirely.

Sara and Alan dive into real-world leadership scenarios, including high-pressure boardrooms, investor pitches, and organizational change initiatives. Alan shares a personal story about losing composure under pressure and how reframing emotional triggers transformed his leadership effectiveness. This highlights a key theme: self-awareness is the gateway to leadership transformation.

Alan also connects leadership signals and the signal architecture to measurable business outcomes. When leaders improve alignment and consistency, organizations experience:

Looking ahead, Alan stresses that the future of leadership will demand even greater emotional intelligence. As AI and automation reshape business, human connection, authenticity, and mastering the signal architecture will become the defining competitive advantage.

Key Moments:

[00:00:43] Introduction to Leadership Signal Architecture

[00:01:02] Why Trust Outweighs Strategy in Leadership

[00:02:04] The Cost of Incongruence in Leadership Behavior

[00:03:31] Warning Signs of Organizational Struggle

[00:05:08] Signals of High-Performing, Aligned Organizations

[00:07:07] The Five Core Components of Leadership Signals

[00:10:12] Unintentional Signals That Sabotage Performance

[00:13:03] Business Impact of Strong Leadership Signals

[00:15:08] Managing Pressure and Reframing Emotional Triggers

[00:21:46] Good Leaders vs Transformational Leaders

[00:30:57] Identifying Competitive Edge in Leadership Teams

[00:43:00] The Future of Leadership in an AI-Driven World

About Alan McLaren:

Alan McLaren is a former International Chair of YPO GOLD,  with more than 37,000 leaders in 140 countries. His YPO  leadership experience informs STRATA’s vantage point on governance, leadership expectations, and scale.

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Resources discussed in this episode:

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In this episode of Transformational Thinkers, Sara Sheehan and guest Victoria Pelletier discuss what it takes to lead with strength, vulnerability, and clarity in today’s evolving business landscape.

Victoria addresses a critical tension in modern organizations: the balance between people, process, and data. While data integrity is essential, she emphasizes that organizations cannot afford to wait for perfect systems before moving forward with innovation. Leaders must act strategically while continuing to refine their data foundations.

Victoria reflects on what she has had to unlearn over time, including the outdated belief that leaders must suppress vulnerability. Instead, she highlights the importance of showing up authentically, while continuing to work on personal growth areas such as patience and self-awareness. She and Sara also talk about decision-making under pressure, and Victoria shares a defining moment during a series of acquisitions. Faced with conflicting data and intuition, she chose to trust her instincts about retaining key talent. That decision preserved significant client relationships, reinforcing the importance of balancing analytics with human insight. Over time, Victoria developed deeper relationships with the team, which is critical for high-stakes account development efforts.

In discussing the human side of leadership, they dive into how personal experiences shape executive performance. Victoria candidly shares challenges related to family, mental health, and identity, underscoring that resilience is not just a professional competency but a deeply personal journey. Victoria describes confidence versus ego as a fine line that requires continuous self-awareness and humility. Leaders must learn to communicate their value clearly while remaining grounded and open to growth.

A critical leadership mistake she highlights is the tendency to make exceptions for high performers who violate company values. These exceptions, while often rationalized, can erode trust and damage organizational culture over time. Victoria also outlines what signals readiness for greater responsibility: high performance, a willingness to stretch beyond comfort zones, and the ability to embrace failure as part of growth. She emphasizes that leaders must actively develop their people, not just drive results.

Victoria shares her mindset of being “unstoppable” and maintaining a no-excuses approach to achieving goals. She reinforces that growth happens in discomfort and that leaders must be willing to step into uncertainty.

As the conversation closes, Victoria and Sara reflect on legacy and long-term success. They challenge the traditional focus on titles and financial outcomes, emphasizing instead the importance of impact, relationships, and the kind of person a leader becomes. True success is measured by the lives influenced and the culture created, not just the results delivered. 

Key Moments:

00:00:00 – The Role of People, Data, and AI in Business Transformation

00:01:18 – What Leaders Must Unlearn to Evolve

00:02:44 – High-Stakes Decision Making: Logic vs Intuition

00:05:21 – The Personal Weight Leaders Carry

00:06:25 – Emotional Intelligence Under Pressure

00:07:32 – The Cost of Delayed Decisions

00:09:43 – Confidence vs Ego in Executive Leadership

00:12:14 – The Hidden Leadership Mistake That Erodes Culture

00:14:38 – Identifying High-Potential Talent

00:16:57 – Building Courage and Operating in Discomfort

00:19:35 – The Impact of Failure on Leadership Identity

00:23:31 – Rethinking Success, Legacy, and What Truly Matters

About Victoria Pelletier:

Victoria Pelletier is a transformational C-suite executive, board director, keynote speaker, and author known for driving business growth, leadership excellence, and cultural transformation across global organizations. With more than two decades of senior leadership experience, she has held executive roles in complex, high-growth environments, where she has led large-scale transformations and delivered measurable business results.

A passionate advocate for diversity, equity, and inclusion, Victoria is widely recognized for her bold, no-excuses leadership style and her commitment to helping individuals and organizations reach their full potential. Through her speaking, writing, and advisory work, she empowers leaders to elevate performance, embrace resilience, and lead with authenticity in today’s rapidly evolving business landscape.

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Resources discussed in this episode:

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In this episode of Transformational Thinkers, Sara Sheehan interviews Nick Jain, CEO of Eagle Rock CFO, an analytically driven firm leveraging AI to transform financial operations, HR functions, and strategic decision-making. Nick is a seasoned CEO known for his expertise in scaling businesses. Eagle Rock CFO is using AI as a central offering to drive client organizational growth. 

Nick begins by revealing one of the earliest indicators of business decline: a lack of urgency and productivity within teams, resulting in stagnation. When employees are no longer fully engaged, it often signals deeper operational or market misalignment. He emphasizes the importance of distinguishing between internal execution issues and external market shifts, noting that leaders must act decisively before problems appear in financial metrics, emphasizing the need to make positive ROI decisions daily.

At the core of Nick’s scaling philosophy is a simple but powerful principle: every decision must generate positive incremental return on investment. Financial performance is his most important indicator of business health.

Sara and Nick discuss leadership under pressure. Nick shares his personal leadership challenges, particularly the intricacies of stepping into organizations with established leadership cultures and making unpopular decisions for long-term value creation. He underscores that effective CEOs must prioritize outcomes over approval, especially during periods of transformation.

A central theme of the episode is Nick’s approach to risk. Rather than relying on intuition, he applies a quantified, probability-based framework to evaluate decisions. Leaders must assess expected value while also considering path dependency, ensuring that no single decision eliminates their ability to continue operating and competing.

Sara and Nick then explore the transformative power of AI in business. Through Eagle Rock CFO’s proprietary platform, Nick demonstrates how AI-based systems can analyze vast datasets, identify profit opportunities, and surface risks in real time. What traditionally required dozens of hours of manual analysis can now be completed in seconds, delivering actionable insights to businesses across industries. The platform identifies overlooked opportunities such as pricing strategies, operational inefficiencies, and even risk exposures like missing insurance coverage. By reviewing diverse data sources, the system continuously generates recommendations designed to improve profitability and resilience.

Nick also introduces a paradigm shift in how AI should be used. Rather than asking narrow, task-based questions, leaders should adopt open-ended prompts such as “How do we make this business better?” This approach allows AI to think more holistically, uncovering insights that traditional workflows might miss.

Nick argues that tomorrow’s leaders must combine analytical rigor with technological fluency, as AI becomes central to decision-making and organizational design. He highlights the growing accessibility of advanced intelligence, enabling even small businesses to leverage capabilities once reserved for large enterprises.

The conversation takes a deeper turn as Nick reflects on the societal implications of AI. While it drives efficiency and growth, it also raises profound questions about meaning, work, and human connection. As AI impacts positions, individuals, and certain forms of interaction, leaders must grapple with the broader impact AI has on the workforce and communities. Additionally, Nick highlights there has been a huge reduction in cost to use AI in all use cases, workflows, and applications for businesses of all sizes, paving the way for a significant increase in AI use, adoption, and impacts to the future of work.

The episode concludes with a forward-looking perspective on leadership, growth, and the importance of adapting to an AI-driven world while maintaining a focus on human value and purpose.

Key Moments:

00:00:01 Early Warning Signs of Business Stagnation

00:00:33 Internal vs External Causes of Business Decline

00:01:31 The Power of Positive Incremental ROI

00:02:32 Leading Through Unpopular Decisions

00:05:37 Quantifying Risk and Making Smarter Bets

00:06:50 The Leadership Habit Most CEOs Overlook

00:07:58 How AI is Replacing Traditional CFO Work

00:09:45 Turning Data Into Profit and Risk Mitigation

00:27:06 Rethinking AI Impact: From Task Execution to Strategic Thinking

00:23:00 The Future of Back Office Functions with AI

00:30:10 Scaling Lessons: Data Visibility and Decision Making

00:39:16 The Hidden Risk of AI: Meaning, Work, and the Future of Humanity

About Nick Jain:

Nick Jain is the CEO of Eagle Rock CFO, a tech-enabled fractional CFO firm that leverages autonomous AI to help businesses improve profitability, optimize operations, and scale intelligently. With experience scaling companies across multiple industries, Nick brings a highly analytical approach to leadership, risk management, and decision-making.

Nick has an MBA from Harvard Business School and investment experience with Bain Capital private equity and Greenlight public equities.

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Resources discussed in this episode:

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Contact Nick Jain | Eagle Rock CFO

Contact Sara Sheehan | Sara Sheehan Consulting:

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In this thought-provoking episode, Sara Sheehan delivers a strategic and human-centered perspective on artificial intelligence and its impact on business, leadership, and society. She emphasizes that AI is not autonomous. It reflects the priorities and decisions of those who design and deploy it.

The Transformation of Work Requires Human Leadership

AI is reshaping how work is structured across industries. However, the true challenge is not automation. It is ensuring that humans remain in control of how work is defined and valued.

Sara highlights that leading organizations will:

As routine tasks become automated, human value shifts toward leadership, creativity, trust building, and ethical governance.

Education Must Evolve to Develop Leaders

To support this shift, education systems must prioritize:

Sara reinforces that developing capable, self-aware leaders is essential for navigating an AI-integrated future.

Economic Systems Require Active Human Stewardship

AI will unlock unprecedented productivity, but economic outcomes will depend on how leaders design systems around it.

Key leadership responsibilities include:

Healthy economies are not automatic. They are intentionally created and sustained by leaders.

Preserving Human Agency in an AI-Driven World

One of the greatest risks is over-reliance on AI systems. Sara stresses that humans must retain accountability and decision-making authority.

Organizations must:

Agency is not preserved by default. It requires disciplined leadership and continuous awareness.

Redefining Meaning and Purpose Beyond Work

As AI reshapes traditional career structures, individuals must actively define meaning and purpose.

Sara explores how fulfillment will increasingly come from:

Organizations that support the whole person will build stronger, more engaged teams.

Adapting to Rapid Change with Resilience

The pace of change is accelerating, placing new demands on individuals and organizations.

To thrive, leaders must focus on:

Resilience is built through both individual capability and collective strength.

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Key Moments

00:00:03 Introduction to AI Leadership and Human Responsibility

00:02:13 The Five Biggest Concerns in an AI-Driven World

00:02:50 AI and the Transformation of Work

00:03:40 The Evolving Role of Human Skills in Business

00:04:33 Rethinking Education for the Future of Work

00:05:30 Supporting Workforce Performance and Well Being

00:06:00 Designing Economic Systems in the Age of AI

00:06:56 The Role of Business Leaders in AI Integration

00:08:00 Preserving Human Agency and Decision Making

00:09:25 Leadership, Critical Thinking, and AI Governance

00:10:30 Redefining Meaning and Purpose Beyond Work

00:12:07 Building Resilience and Adapting to Rapid Change

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What if the key to unlocking innovation and leadership performance is as simple as movement?

In this compelling episode of Transformational Thinkers with Sara Sheehan, Sara welcomes Joel Heath, entrepreneur, innovator, and CEO of FluidStance, a company focused on creating products that bring movement into the workplace.

Joel shares his transformative journey from concept to company, illustrating how his innovative leadership is reshaping our understanding of workplace culture and education. As we explore the challenges many face in static environments, Joel candidly reflects on his experiences as a father witnessing his son’s transition from a playful preschool to a rigid kindergarten. This pivotal moment ignited his passion for creating products that promote movement and enhance creativity. Joel set out to design solutions that restore dynamic movement in modern workspaces. The result was FluidStance, a brand built on the belief that physical movement fuels cognitive performance, emotional engagement, and innovative thinking.

He highlights the critical role of innovation in fostering environments that empower employees, emphasizing how physical activity can lead to greater productivity and a thriving workplace culture. One of the most powerful frameworks he discusses is the 70-20-10 innovation model, which allocates resources across three strategic areas.

Throughout our conversation, we touch on essential themes such as the delicate balance between innovation and operational stability, the importance of teamwork, and the cultivation of a culture that embraces both performance and play. Joel’s insights into leadership excellence and transformational leadership provide valuable lessons for executives and aspiring leaders alike, offering a roadmap for navigating the complexities of organizational growth and business transformation.

We also delve into the challenges of over-innovation and the necessity of emotional intelligence in leadership. Joel’s perspective on maintaining a dynamic balance in life and business serves as a clarion call for all leaders striving for real-world change. He shares actionable strategies for enhancing communication in leadership and optimizing talent, ensuring that organizations not only adapt but thrive in extraordinary times.

This episode is a treasure trove of insights for anyone interested in change management, employee empowerment, and the transformative power of creativity in the workplace.  Joel emphasizes the value of what he calls the one percent rule, intentionally safeguarding a small portion of time dedicated to reflection, exploration, and renewal. This protected time often leads to breakthrough ideas and deeper clarity for leaders. Join us as we uncover the innovative leadership strategies that can help you and your organization master change management and achieve audacious goals.

This episode offers a powerful perspective for leaders embracing innovation, driving meaningful change, and facilitating business growth in a rapidly evolving business landscape.

If you are ready to rethink how leadership, creativity, and performance intersect, this episode will challenge you to move forward in new ways. Don’t miss out on this opportunity to learn from one of the brightest business executives in the world.

Key Moments:

00:00:00 – Movement Sparked the Business

00:01:40 – The Problem with “Sit to Focus”

00:03:20 – Why Movement Improves Thinking

00:04:45 – When You Lose Your Creative Edge

00:05:50 – Entrepreneur vs. Artist Mindset

00:08:10 – Creativity Needs Structure

00:09:10 – The Athlete Mindset in Business

00:10:25 – The Truth About Building FluidStance

00:12:40 – The Danger of Too Many Ideas

00:15:35 – The 70-20-10 Growth Framework

00:20:30 – Designing Workplaces That Move

00:22:35 – Avoiding Chaos or Stagnation

00:24:20 – Why Play Is a Leadership Advantage

00:28:30 – The 1% That Drives Performance

00:36:15 – Grit, Growth, and What Leaders Leave Behind

About Joel Heath:

Joel Heath is a consumer brand and product architect, front-end innovator, and CEO. He develops insight-led strategies that shape category-defining products, reposition brands, and drive growth with purpose. He is the Founder and CEO of FluidStance, and he also advises companies in the biotech and outdoor categories. FluidStance is reimagining the workplace by bringing movement, energy, and well-being into static environments. Joel is also taking on select fractional and board roles where he can contribute to brand, product, and growth strategy within his leadership role.

Previously, he helped lead the turnaround of Teva as part of the Deckers Brands (NASDAQ: DECK) leadership team. His first successful exit was an experiential brand agency in Vail, Colorado, where they created campaigns for Volkswagen, Native Eyewear, Payday Candy Bars, and Sports Illustrated. Joel conceived of and created the GoPro Mountain Games, the largest outdoor adventure event in the world, broadcast on NBC and CBS. In addition to athletic events, the GoPro Mountain Games include a mountain photography competition, adventure film school, film festival, interactive exhibition, live music, and mountain lifestyle parties. 

Joel works as a strategic advisor, helping organizations clarify their why, develop disruptive product concepts, and build authentic connections with their audiences. His leadership spans startups, global brands, and purpose-driven organizations, with a focus on long-term value creation.

Beyond business, he is a founding board member of First Descents, a nonprofit that delivers life-changing outdoor experiences for young adults surviving cancer and other serious health challenges.

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Resources discussed in this episode:

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What if the key to thriving in the age of AI lies not in reducing your workforce but in empowering it? In this solo episode of Transformational Thinkers with Sara Sheehan, host Sara Sheehan delves into the often-overlooked truth about the role of employees amidst the rise of agentic AI systems and AI oversight.

Agentic AI systems do not simply automate tasks. They reshape the economics of work, speed, scale, and consequence. While many leaders focus on cost reduction and role replacement, Sara makes a compelling case that AI transformations actually increase the strategic importance of employees.

Why? Because autonomous systems amplify whatever infrastructure they inherit. Broken workflows, poor data governance, unclear decision rights, and cultural fragmentation do not disappear with AI. They accelerate.

This episode walks through the ten highest impact contributions employees make during an agentic AI transformation. Listeners will gain insights into leadership excellence and transformational leadership, discovering how to foster a workplace culture that nurtures employee empowerment and talent optimization. Sara shares real-world change stories that highlight the transformative power of viewing AI oversight not as a workforce reduction tool but as a workforce multiplier that enhances human capabilities. This episode is packed with change management strategies and innovative leadership insights that will inspire leaders to embrace a growth mindset and cultivate creativity within their teams.

The Ten Highest Value Human Contributions in an AI Transformation

1. Conducting Rigorous Process Reviews

Before automation, employees surface hidden inefficiencies, bottlenecks, and failure points. They map how work truly happens, not how it appears in documentation. For CEOs, this is margin protection and scalability engineering.

2. Data Cleanup and Governance

AI systems are only as reliable as the data they consume. Employees safeguard decision infrastructure through data normalization, ownership definition, and governance discipline. This is enterprise risk management in action.

3. Human Oversight of Autonomous Systems

Autonomous systems introduce a new category of risk: invisible error at machine speed. Employees monitor outputs, detect anomalies, manage model drift, and intervene in high-impact decisions. Oversight enables controlled acceleration rather than uncontrolled exposure.

4. Exception Handling and Contextual Judgment

Business reality is complex and dynamic. Employees protect value at the boundaries where AI struggles, including ambiguous ethical situations, regulatory shifts, and strategic trade-offs. Automation scales the process. Humans scale judgment.

5. Training and Refining AI Agents

Employees transform generic AI into a proprietary advantage. Through feedback loops, domain corrections, and system refinement, they align AI capabilities with competitive context.

6. Cross-Functional Translation

Agentic AI transformations often stall due to silos. Employees who bridge operations, finance, legal, IT, and customer experience create coherence. They translate technical capability into business outcomes and reduce political drag.

7. Identifying High Value Automation Opportunities

Not all automation creates ROI. Employees closest to the work distinguish between high-leverage opportunities and novelty projects. Their insight strengthens capital allocation discipline.

8. Driving Change Adoption and Cultural Stability

AI adoption is psychological as much as technical. Employees stabilize performance during uncertainty by modeling new behaviors and reducing resistance through understanding.

9. Risk Detection and Ethical Safeguards

Bias, compliance conflicts, and unintended consequences can scale rapidly in AI environments. Employees serve as early detectors, integrating human values and organizational norms into governance frameworks.

10. Continuous Improvement and System Evolution

An agentic AI transformation is not a project with an end date. It is a continuous capability shift. Employees drive iterative refinement, integration expansion, and performance optimization, ensuring AI becomes a compounding advantage rather than a depreciating tool.

As you listen, consider how you can implement these innovative leadership approaches, communication strategies and change management techniques to engage your stakeholders effectively. Whether you are a CEO, CHRO, or a leader in human resources, this episode offers invaluable perspectives on navigating the future of work and driving organizational change.

Sara leaves leaders with a powerful question:

The issue is not how many roles AI will replace. The issue is how to maximize the unique value humans contribute alongside autonomous systems.

High-performing organizations treat employees as co-architects of transformation. They elevate people into roles as designers of intelligent workflows, stewards of data integrity, governors of autonomous systems, and guardians of judgment and ethics.

AI may redefine industries. But organizations that win will deliberately cultivate the human capabilities that AI cannot replicate: contextual reasoning, ethical discernment, adaptive thinking, and strategic judgment.

Technology transforms organizations. People determine whether that transformation creates enterprise value or destroys it.

If you are serious about AI-driven business transformation, AI oversight, workforce strategy, and sustainable competitive advantage, this conversation will reshape how you think about human capital in the age of autonomous systems.

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Key Moments:

00:00:01 Introduction: Agentic AI Transformation and the Future of Workforce Strategy

00:01:36 Chapter 1: Business Process Optimization for Scalable AI Implementation

00:02:47 Chapter 2: Data Governance and Data Quality Management in Enterprise AI Systems

00:03:53 Chapter 3: AI Governance and Human Oversight in Autonomous Systems

00:04:50 Chapter 4: Human Judgment in AI Decision Making and Exception Management

00:05:38 Chapter 5: Training, Prompt Engineering, and AI System Optimization for Competitive Advantage

00:06:33 Chapter 6: Cross-Functional Leadership in Enterprise AI Transformation

00:07:26 Chapter 7: Strategic Automation Planning and High ROI AI Use Cases

00:08:16 Chapter 8: Change Management Strategy for AI Adoption and Workforce Transformation

00:08:39 Chapter 9: Ethical AI, Risk Mitigation, and Compliance in AI-Driven Organizations

00:09:40 Chapter 10: Continuous Improvement and AI System Evolution for Long-Term Business Growth

00:10:29 CEO Strategy: Human AI Collaboration as a Competitive Advantage

00:11:05 Closing: AI Workforce Transformation and Enterprise Value Creation

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Contact Sara Sheehan | Sara Sheehan Consulting:

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In this episode, host Sara Sheehan welcomes Jed Ayres, the visionary CEO of ControlUp, a leader at the forefront of digital employee experience and autonomous IT operations. Jed reflects on his early years owning and operating a hotel and restaurant, where performance feedback was immediate and ruthless. These formative experiences shaped his servant leadership philosophy, which emphasizes empathy, accountability, and trust as the foundation of high-performing organizations. Jed’s unique journey reveals invaluable lessons in leadership excellence and transformational leadership.

Jed explains how the shift to remote and hybrid work during the pandemic revealed a critical gap in traditional IT operations. While companies spent years prioritizing customer experience, employee digital experience lagged behind. This lag created friction, anxiety, and lost productivity. From that, Jed led the evolution of ControlUp from a deep technology platform into a cutting-edge, unified digital employee experience solution. As organizations navigate the complexities of the digital employee experience, understanding the human element becomes essential. He clarifies the difference between managing technology performance and managing employee experience, highlighting how real-time telemetry, automation, and AI eliminate repetitive troubleshooting and dramatically lower ticket volumes. Gartner predictions support this shift, suggesting organizations that fail to adopt these platforms risk falling behind operationally and competitively.

Sara and Jed discuss how AI transforms IT from a reactive cost center into a strategic enabler. By using real-time data contextualized around individual employees, AI can identify issues, recommend fixes, and even remediate problems. This not only reduces operational drag but also frees IT teams to focus on higher-value strategic work. Jed also addresses common misconceptions about DEX, urging organizations to prioritize core IT operational efficiencies before venturing into HR aspects. This strategic alignment is crucial for fostering an environment where talent can thrive, ultimately leading to organizational growth and innovation in leadership.

From a leadership perspective, Jed emphasizes that successful digital workplace transformation requires executive sponsorship, cross-functional collaboration, and cultural readiness. Successful organizations formalize digital employee experience at the board level, invest in dedicated ownership, and commit to long-term partnerships rather than isolated tool deployments. With these accelerating changes in how we work, Jed emphasizes the urgent need for seamless technology experiences that empower employees and enhance productivity. This episode is not just a conversation; it’s a clarion call for transformational thinkers to embrace change management strategies that cultivate workplace culture and enhance communication in leadership.

The episode posits a bold prediction: In the near future, manual troubleshooting will be viewed as reckless and wasteful. Autonomous IT operations powered by AI will become the standard, fundamentally reshaping how organizations operate and how leaders think about productivity and human potential. Don't miss out on this opportunity to engage with one of the industry's leading voices in business transformation. Tune in to Transformational Thinkers with Sara Sheehan and discover how to transform challenges into opportunities for growth and success. 

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About Jed Ayres: 

Jed Ayres brings vast experience in leading multinational software organizations to ControlUp, successfully executing strong organic and inorganic growth strategies, building groundbreaking leadership teams, executing strong partnerships, and expanding internationally. Most recently, Ayres served as CEO of IGEL, where he was instrumental in its acquisition by TA Associates and positioning it as a market leader. Prior to that, Ayres was responsible for the strong growth in category leader AppSense (acquired by Ivanti) and held executive leadership positions with MCPc (acquired by Logicalis), MTM Technologies, and GE Capital IT Solutions. 

Key Moments:

00:00:01 – Welcome and Introduction to Jed Ayres

00:01:30 – Hospitality Roots and the Servant Leadership Mindset

00:03:00 – Why Digital Employee Experience Became a Strategic Imperative

00:04:45 – The Hidden Cost of Poor Technology Experiences at Work

00:06:20 – Optimization vs Monitoring in Digital Employee Experience

00:08:10 – From Legacy IT Tools to Real Time Data and Automation

00:10:00 – Why AI Is Perfect for Eliminating Repetitive IT Work

00:12:45 – Reframing DEX as a Business Outcome for CEOs and Boards

00:15:30 – Tool Consolidation and the Financial Impact of Automation

00:18:00 – Cutting Through Data Noise with AI Driven Insights

00:20:15 – Frontline Workers, Brand Experience, and Digital Friction

00:23:20 – Common Misconceptions About Digital Employee Experience

00:26:15 – DEX as the Gateway to Autonomous Endpoint Management

00:29:45 – Leadership, Trust, and Empowerment in Transformation

00:45:10 – A Bold Prediction for the Future of Work and IT Operations

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Contact Sara Sheehan | Sara Sheehan Consulting:

• SaraWSheehan.com
• Sara Sheehan on LinkedIn
• Meet with Sara
• Submit Questions or Feedback to Sara

Contact Jed Ayres | ControlUp:

• Website: ControlUp.com
• LinkedIn: JedAyres

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