In this episode of Swimming with Sharks, host Kevin J. Dean speaks with Brian J. Esposito — entrepreneur, investor, and founder of Esposito Intellectual Enterprises — about the real and lasting impact of AI on business, jobs, and society.

Brian shares candid insights on the responsibilities companies and investors have when adopting AI technologies, and why many are overlooking the long-term consequences for workers, communities, and the economy. With decades of experience working across sectors, Brian offers a unique perspective on balancing innovation with ethics and impact.

Topics Covered:
The reality vs. the hype around AI
How businesses should approach the future of work
Risks of overlooking AI’s societal impact
Why empathy and long-term thinking matter now more than ever

Subscribe to Swimming with Sharks for more expert conversations on AI, enterprise strategy, and leadership in a transforming world.

#FutureOfWork #AIImpact #BrianEsposito #EnterpriseAI #BusinessLeadership #AIandSociety #SwimmingWithSharksPodcast #KevinJDean

In this episode of Swimming with Sharks, Kevin Dean sits down with David Pearlman, Senior Director of Education at Adobe, to explore how artificial intelligence is reshaping enterprise operations, leadership, and the way we learn.

Drawing on decades of experience at Microsoft and Adobe, David shares how AI is helping reduce noise in the workplace, accelerating asynchronous education, and redefining the role of leadership. From improving email efficiency to navigating shadow AI and compliance, this conversation cuts through the hype and gets to the heart of what meaningful AI adoption looks like.

What you'll learn:

• How AI helps leaders focus on people, not process
  Why personalized learning is replacing traditional models
• The risks of shadow AI and the importance of governance
• How AI can elevate — not eliminate — human work

This is a practical, insightful conversation for business leaders, educators, and enterprise professionals preparing for what’s next.

Connect with the Guest:
David Pearlman on LinkedIn – linkedin.com/in/davidmpearlman

Hosted by Kevin Dean
Founder, ManoByte – linkedin.com/in/kevinddean

In this episode, Kevin Dean sits down with Anthony Coppedge to discuss the rapid changes in technology, leadership, and business strategy. With the rise of Generative AI (GenAI), businesses are facing a transformation as significant as the advent of the internet and mobile technology. But how should organizations adapt, align, and think differently to stay ahead?

🔹 Key Topics Covered:
✅ The rate of change vs. individual technological shifts
✅ Why GenAI is a force multiplier – but not a silver bullet
✅ The importance of alignment and clarity in leadership
✅ How to move beyond vanity metrics to focus on real value
✅ Why organizational culture and empathy are crucial in the AI era
✅ The role of agentic AI in the future workforce

🔥 "More of the wrong thing faster is NOT winning!" – Anthony Coppedge

💡 If you’re a leader, entrepreneur, or innovator looking to navigate the future of AI and business transformation, this conversation is packed with insights you won’t want to miss!

🎵 Bonus: Anthony shares a personal music recommendation from his jazz-legend grandfather, Burgess Surges – check it out!

In this episode of Swimming with Sharks, Kevin Dean, CEO of ManoByte, is joined by Rob Ryan, Head of Thought Leadership at WorkGrid Software, for an in-depth discussion on the role of conversational AI in streamlining employee workflows and improving internal communication. Rob shares his insights on organizational change, the evolution of employee experience platforms, and the importance of aligning AI projects with business goals.

Introduction: Kevin introduces Rob Ryan, who has extensive experience in organizational strategy and technology deployment. Rob provides background on WorkGrid Software and its mission to reduce digital friction in the workplace.

Interview Highlights:

• Conversational AI as a Digital Assistant: Rob explains how WorkGrid leverages NLP and machine learning to create digital assistants that streamline employees’ day-to-day tasks. He discusses how conversational AI can reduce digital distractions by integrating with existing tech stacks and bringing actionable insights directly to employees.
• Getting Started with AI Projects: The conversation explores practical steps for organizations to initiate AI projects, emphasizing the importance of quick wins and internal use cases. Rob shares advice on piloting AI initiatives, mitigating risks, and developing a governance strategy to ensure AI aligns with business objectives.
• Transforming Employee Experience with AI: Rob highlights how conversational AI can enhance the employee experience by reducing app hopping and context switching, ultimately fostering a more productive and engaging work environment. He emphasizes that AI should assist, not replace, the human workforce.

Key Takeaways:

• Building an AI Strategy: Rob advises organizations to start with low-risk, high-value AI use cases that support internal goals and gradually expand based on proven results.
• Importance of Governance: A strong governance framework is essential for AI projects to ensure that they are sustainable and that technology is used ethically and effectively.
• Prioritizing Employee Experience: By integrating AI into the flow of daily tasks, companies can improve employee engagement and reduce friction, allowing employees to focus on high-value work.

In this insightful episode of Swimming with Sharks, Kevin Dean, CEO of ManoByte, sits down with Amelia Jones, Principal Customer Success Manager at Mural, to discuss the role of AI in enterprise environments and how visual collaboration can enhance business processes. Amelia shares her experiences from Mural, highlighting the impact of human-centered design and agile methodologies in fostering better decision-making and collaboration.

Introduction: Kevin introduces Amelia, who brings nearly a decade of experience in customer success and a passion for human-centered design. They dive into Mural’s visual collaboration platform and how it reshapes traditional workflows.

Interview Highlights:

• Visual Collaboration for Better Decision-Making: Amelia explains how Mural transforms linear tasks, like spreadsheets and to-do lists, into more engaging and collaborative visual experiences. She emphasizes how visual tools can foster better communication and alignment, especially when mapping out workflows.
• AI in the Enterprise: The conversation explores how AI can assist in ideation and decision-making processes, with Amelia stressing that AI should enhance human creativity, not replace it. She discusses real-world use cases where Mural helps enterprises document, plan, and evaluate AI initiatives.
• Human-Centered Design & Agile in AI Projects: Amelia shares her expertise on how organizations can leverage human-centered design and agile workflows to better implement and scale AI initiatives. She discusses techniques like abstraction laddering and the five whys, which Mural facilitates to help businesses identify and solve the right problems.

Key Takeaways:

• AI as a Collaborative Tool: AI should act as a collaborator, assistant, and coach, helping teams to innovate while keeping creativity and problem-solving at the forefront.
• Documenting AI Processes: Mural plays a vital role in helping organizations document and map out their AI processes, ensuring that initiatives are well-planned and stakeholder engagement is prioritized.
• Balancing AI Excitement with Practicality: While AI can be a powerful tool, Amelia advises businesses to be deliberate in its implementation, ensuring that it adds tangible value to workflows.

In this exciting episode of Swimming with Sharks, Kevin Dean, CEO of ManoByte, welcomes Mike Lyons, founder of KaiRise, to explore the intersection of Agile methodologies and generative AI. Mike shares his unique journey through the IT landscape, from small firms to large consulting agencies, shedding light on how AI is shaping business processes and the power of agility in driving innovation.

Introduction: Kevin introduces Mike Lyons, who has decades of experience in IT, ranging from higher education to government, finance, and non-profits. They dive into Mike’s deep insights on Agile ways of working and how organizations can capitalize on AI technology for better decision-making and enhanced efficiency.

Interview Highlights:

• Agile in the AI Era: Mike explains how Agile is not just about frameworks like Scrum, but about fostering a mindset of adaptability and rapid learning, especially when integrating AI tools.
• Learning Through Failure: Drawing on personal experiences, Mike discusses how businesses can learn more from failures than successes, particularly with emerging technologies like generative AI.
• Experimentation and Innovation: The conversation explores why companies need to allow a "thousand flowers to bloom" and how innovation thrives at the edges—outside traditional boardroom strategies.

Key Takeaways:

• Embrace Agile: Organizations must adopt Agile ways of working to stay competitive, especially in today’s fast-paced AI-driven world.
• Security vs. Innovation: Striking a balance between encouraging experimentation with AI tools and maintaining data security and governance is crucial.
• Future of AI: The episode concludes with a discussion on the global implications of AI, including how it can address accessibility and humanitarian challenges, and what’s next in the rapidly evolving tech landscape.

Episode Overview: In this episode of Swimming with Sharks, Kevin Dean, CEO of ManoByte, sits down with Stephen Stouffer, Director of Automation Solutions at Tray.ai. Stephen discusses his journey from marketing automation to becoming a leader in AI integration and shares valuable insights on leveraging AI for enterprise success.

Introduction: Kevin introduces Stephen Stouffer, who brings extensive experience from various industries, including enterprises, agencies, startups, and nonprofits. Stephen has been deeply involved in the AI space, focusing on how organizations can harness AI to streamline operations and gain a competitive edge.

Interview Highlights:

• AI Accessibility: Stephen emphasizes that generative AI is for everyone, from beginners to technical experts, and encourages organizations not to be intimidated by its potential.
• Enterprise Challenges: He discusses the importance of feeding AI with the right data and context to maximize its effectiveness, stressing that while AI can simplify tasks, thoughtful deployment is crucial.
• Tray.ai's Role: Stephen explains how Tray.ai’s rebrand focuses on integrating AI into workflows securely and efficiently, introducing features like the Merlin connectors that enhance data privacy and automation.

Key Takeaways:

• Start Small: Organizations should begin with simple AI implementations, focusing on teams that are open to change.
• Security and Context: Ensuring data security and providing AI with proper context are vital for successful enterprise AI adoption.
• Future of AI: The AI landscape is rapidly evolving, and organizations must adapt quickly to stay ahead, with AI becoming an integral part of daily operations across industries.

In this episode of Swimming with Sharks, Kevin Dean, CEO of ManoByte, sits down with Wendy McHenry, the Head of Solutions Engineering at CData Software, for an insightful discussion on customer operations and the evolving tech landscape. Wendy brings a wealth of experience from her journey in tech, starting as a statistician and moving through various leadership roles in sales engineering, particularly in financial services and government sectors.

Introduction:

Kevin introduces Wendy McHenry, highlighting her impressive career trajectory from a statistician to a leader in solutions engineering. Wendy’s unique path showcases her passion for technology and her commitment to improving customer experiences.

Interview Highlights:

• Wendy’s Career Path: Wendy shares her unconventional entry into tech, beginning as a statistician and transitioning into a sales engineer role at SAS Software. Her journey reflects a deep understanding of customer needs and the importance of aligning tech solutions with business goals.
• Challenges in Customer Operations: Wendy discusses the complexities customers face in today’s competitive environment, emphasizing the difficulties of navigating tight budgets, internal reorganizations, and the fear of change. She underscores the need for companies to build trust and guide customers through tech modernization.
• AI and Automation in Tech: The conversation shifts to the role of AI and automation in reshaping the tech industry. Wendy offers insights into how these technologies are helping companies do more with less, while also raising important ethical considerations. She predicts that while AI will not eliminate tech jobs, it will significantly enhance efficiency and innovation.
• The Role of Data Analytics: Wendy, a data enthusiast at heart, explores the critical role data analytics plays in driving business decisions and improving customer outcomes. She highlights the importance of staying at the forefront of data science to address challenges in various industries, from financial services to emergency response.
• Diversity, Equity, and Inclusion in Tech: Wendy also shares her passion for DEI initiatives, particularly in creating psychologically safe workplaces. She emphasizes the importance of leaders fostering inclusive environments to drive positive change in the tech industry.

Key Takeaways:

• Trust and Empathy: Building trust with customers is crucial in today’s fast-changing tech landscape. Companies must listen to customer concerns and provide solutions that ease the fear of change.
• Leveraging AI for Efficiency: AI and automation are powerful tools that can help businesses maximize resources, but they must be implemented thoughtfully, with ethical considerations in mind.
• Data as a Driving Force: Data analytics is at the core of successful tech operations, enabling companies to make informed decisions and respond effectively to challenges.
• Inclusive Leadership: Creating diverse and inclusive teams is essential for fostering innovation and ensuring the tech industry remains a welcoming space for everyone.

In this episode of Swimming with Sharks, Kevin Dean, CEO of ManoByte, welcomes Amber Vaden, a dynamic leader in customer operations and success with nearly a decade of experience in the field. Amber brings a unique perspective to customer service, blending her background in education with a deep passion for creating impactful customer experiences.

Introduction:

Kevin introduces Amber Vaden, who has made a significant impact in the world of customer success and operations. Amber's journey began with a desire to teach, which seamlessly transitioned into a career in customer service. Her role allows her to blend empathy with creativity, helping both customers and internal teams achieve success. Known for her innovative approach and commitment to understanding customer needs, Amber is excited to share her insights and experiences on the show.

Interview Highlights:

• Amber’s Path: Amber shares her unique journey from a potential career in teaching to becoming a key player in customer service. She discusses how her background in education informs her approach to creating impactful customer experiences and fostering internal success.
• Core Challenges: Amber identifies a major challenge in customer operations: the difficulty of truly understanding and addressing individual customer needs. She advocates for customized solutions and ongoing feedback to ensure that customer interactions are meaningful and effective.
• Technology vs. Empathy: Amber offers her perspective on the role of technology in customer service, emphasizing that while AI can support operational efficiency, it lacks the empathy that human interactions provide. She stresses the importance of balancing technological tools with a human touch to enhance customer satisfaction.
• Effective Strategies: The conversation delves into practical strategies for managing customer relationships and balancing various responsibilities. Amber highlights the importance of setting realistic expectations and maintaining organization to deliver consistent and thoughtful customer support.
• Empathy in Action: Amber underscores the significance of treating every customer interaction with the same care and respect one would offer to a loved one. She believes that building genuine trust and empathy can transform customer experiences and foster long-term loyalty.
• Looking Forward: Amber is excited about the future of customer service as new technologies and innovative companies emerge. She anticipates that these advancements will offer new ways to enhance customer experiences and drive success.

Key Takeaways:

• Personalized Approach: Understanding and addressing individual customer needs through tailored solutions and feedback is essential for effective customer service.
• Human Touch: While technology can aid in customer service, it should be complemented by the empathy and personal connection that only humans can provide.
• Strategic Balance: Effective customer support involves balancing organizational demands with the need for realistic expectations and consistent, empathetic interactions.
• Future Innovations: Embracing new technologies and strategies will continue to shape and improve the customer service landscape, offering exciting opportunities for growth and enhancement.

In this compelling episode of Swimming with Sharks, Kevin Dean, CEO of ManoByte, sits down with Kári Thor Runarsson, the visionary founder of Cliezen, to explore the dynamic world of customer operations and the intersection of marketing, customer success, and technology. Kári shares his rich, globe-trotting journey from Iceland to Iowa and beyond, offering a unique perspective on the importance of understanding and exceeding customer expectations in both B2B and B2C environments.

Episode Summary:

Introduction: Kevin Dean kicks off the episode by introducing Kári Thor Runarsson, delving into his impressive background and his passion for customer experience (CX) and customer success (CS).

Interview Highlights:

1. Kári’s Journey: Kári discusses his diverse upbringing and professional experiences across multiple countries, emphasizing how these have shaped his approach to customer experience and operations.
2. The Role of Marketing in CX: Kári explains the natural alignment between marketing and customer experience, highlighting how his marketing background has informed his approach to customer success.
3. Challenges in Customer Success: Kári identifies the key challenges facing the customer success industry today, particularly the undervaluation of CS roles and the struggle to quantify their impact.
4. The Impact of AI in Customer Ops: Kári shares his insights on the transformative potential of AI, distinguishing between generative AI and other forms of AI, and discussing how technology can help close the experience gap.
5. Bridging Organizational Gaps: Kári offers advice on improving communication and collaboration across departments, emphasizing the importance of data and analytics in making informed, customer-centric decisions.
6. The Future of CX: Kári predicts the evolution of customer success, focusing on the role of technology in automating routine tasks and allowing professionals to focus on more strategic, high-impact activities.

Key Takeaways:

• Customer Centricity: Successful customer operations hinge on understanding and exceeding customer expectations, tailored to different roles and needs within a client organization.
• Technology as an Enabler: While tools and AI can significantly enhance customer experience efforts, they must be accompanied by a genuine commitment to customer-centricity across the organization.
• Realistic Expectations with AI: While AI offers incredible potential, it’s crucial to maintain realistic expectations and understand its current limitations.
• Communication & Collaboration: Effective customer success requires seamless communication across departments, supported by accurate data and analytics to inform decision-making.