Enterprise Signals

About Enterprise Signals

In this series of podcasts, we will uncover the 'real story' of AI in the mid market space by talking with Chief Information Officers, VP's of IT and Directors of IT to understand what is really happening with AI in the mid market space. We will also uncover that leaders are looking for when they create their SME or CoE AI team. Finally, we will assist candidates on what talents they should hone to help grow their careers and meet the demands of these CIOs, VPs and Directors of IT

Publisher

Tom Welke and Richard Doran

Category

business

Language

en

Explicit

No

First episode

26 May 2026

Latest episode

12 Aug 2026

Latest episodes

8 episodes in the feed.

1. 

   12 Aug 2026

   Sargon Guliana Discusses Inflection Points in your Ai Projects, an The Evolving Role of the CIO

   Sargon Guliana, a seasoned CIO and technology expert, shares insights on digital transformation, AI projects, and talent development. He emphasizes the importance of understanding business problems, communication, and setting realistic AI strategies. Sargon also highlights the significance of critical thinking, challenging assumptions, and recognizing the path to success. The conversation covers the importance of framing and planning AI pilots, the evolving role of the CIO, the significance of data readiness, and the need for collaboration and strategic planning in IT initiatives. It also emphasizes the role of a third party in facilitating alignment and creating a cohesive AI roadmap. Takeaways Digital transformation and AI projects require a focus on solving business problems and setting realistic strategies. Critical thinking, challenging assumptions, and recognizing the path to success are essential skills for AI and technology leaders. AI pilots require upfront planning and stakeholder buy-in The role of the CIO is evolving from service provider to internal consultant and advocate Data readiness and standardization are crucial for successful AI initiatives Collaboration and strategic planning are essential for aligning IT initiatives with business goals A third party can facilitate alignment and create a cohesive AI roadmap Chapters 00:00 Inflection Points in AI Pilots 30:16 Framing and Planning AI Pilots 33:01 The Evolving Role of the CIO 43:02 The Significance of Data Readiness 49:25 Collaboration and Strategic Planning in IT Initiatives 53:23 The Role of a Third Party in Facilitating Alignment

2. 

   6 Aug 2026

   Mark Szkudlarek discuses Customer Experience, Lessons from GE, and How to Not Chase Shiny Objects

   The podcast conversation delves into the real story of AI in the mid-market space, covering topics such as time invested in AI projects, the importance of hackathons, the role of AI as a tool in the toolbox, leadership insights, and the significance of governance and guardrails in AI implementation. The conversation delves into the challenges of AI tool adoption and the importance of governance, customer experience, and leadership in the IT landscape. It emphasizes the need to focus on business requirements, align with executive leadership, and actively listen to build trust and communication. Takeaways AI as a tool in the toolbox Importance of governance and guardrails in AI implementation Governance of AI tools is crucial Customer experience is a key differentiator Active listening and alignment with business requirements are essential for success Chapters 00:00 Introduction to AI in the Mid-Market Space 02:03 The Role of Hackathons in AI Momentum 03:02 AI as a Tool in the Toolbox 07:16 Leadership Insights and Agile Approach 11:13 Lessons from GE and Transformational Organizations 34:00 The Importance of Governance and Guardrails in AI 38:25 The Chasing of the Shiny Object 39:24 Leadership and the End Game 41:08 Center of Excellence and Shadow IT 50:03 Building Trust and Communication 01:09:19 Customer Experience and Business Alignment

3. 

   4 Aug 2026

   Jean Johnson Discusses 'Show Your Work', Failing Fast, and knowing when to Stop before you Start

   The conversation delves into the challenges of maintaining enthusiasm for AI projects, the impact of digital transformation, the importance of data quality, the implications of synthetic data, forecasting with AI, team composition for AI projects, the PMBA combo, and knowing when to quit an AI project. The conversation delves into the role of IT leaders as advisors to the C-suite, the importance of presenting ideas and status in context, and the challenges of evaluating AI project presentations. It also explores the impact of AI on staffing, institutional knowledge, and the pressure to control head count with AI. Additionally, it discusses the importance of redundancy and the people side of efficiency, as well as the future of conversations on AI and business projects. Takeaways Maintaining enthusiasm for AI projects is a challenge due to the length of projects and the impact of digital transformation. Data quality is crucial for AI projects, and understanding synthetic data and knowing when to quit an AI project are important considerations. IT leaders should articulate requests and status in terms of data and context Evaluating AI project presentations requires a focus on the real meat of the project The pressure to control head count with AI requires careful consideration of the long-term impact on staffing and institutional knowledge Chapters 00:00 The Enthusiasm Challenge 01:46 The Length of Projects and Enthusiasm 03:37 The Impact of Digital Transformation 07:29 Data Quality and AI 10:01 Synthetic Data and Its Implications 13:40 Forecasting and AI 17:04 Team Composition for AI Projects 21:20 The PMBA Combo and Its Importance 26:38 Knowing When to Quit an AI Project 29:23 Becoming an Advisor to the C-Suite 30:48 Presenting Ideas and Status in Context 32:11 Articulating the Request and Status 33:07 Elevating the Conversation from IT as a Utility 34:45 Evaluating AI Project Presentations 36:27 Challenges of AI Project ROI 40:22 The Impact of AI on Staffing and Institutional Knowledge 43:02 Total Cost of Ownership and People Side of Efficiency 50:21 Pressure to Control Head Count with AI 52:43 The Importance of Redundancy and People Side of Efficiency 56:00 The Future of Conversations on AI and Business Projects

4. 

   4 Aug 2026

   Ricki Koinig discusses Risks or Rushing, Recruiting Strategies, Getting & Staying at The Big Table

   The conversation covers the role of auditors in innovation, the misconception of AI tools, starting the AI journey, the importance of change management, human in the loop and role evolution, and the danger of cutting expert roles. The discussion emphasizes the need for organizational change management, the integration of human input in automation processes, and the evolution of roles in the context of AI implementation. The conversation covers the caution of rebranding as an AI expert, the importance of understanding business needs, hiring for adaptability, recruitment criteria, innovation framework, organizational change management, earning a seat at the table, and balancing innovation with building blocks for success. Takeaways AI Tools and Automation Organizational Change Management Human in the Loop Role Evolution AI Expertise Caution Domain Knowledge Importance Chapters 00:00 The Role of Auditors in Innovation 02:46 The Misconception of AI Tools 05:09 Starting the AI Journey 13:16 The Importance of Change Management 18:29 Human in the Loop and Role Evolution 26:12 The Danger of Cutting Expert Roles 28:50 Rebranding as AI Expert 30:17 Understanding Business Needs 31:35 Hiring for Adaptability 36:37 Recruitment Criteria and Innovation Framework 45:24 Organizational Change Management 49:04 Earning a Seat at the Table 53:22 Balancing Innovation and Building Blocks

5. 

   17 Jun 2026

   Adrienne Shulman discusses what's working, FOMO and FOBO, and Tools do not Equate to Transformation

   Adrienne Schulman, co-founder of Tenger Ways, discusses the evolution of technology, the role of IT leadership in transformation, and the cultural shift in IT and engineering thinking. She emphasizes the importance of creating a culture of innovation and risk-taking, measuring success with a customer focus, and incentivizing innovation and risk-taking. Additionally, she highlights the value of trying new things, the impact of relationships and trust, and the role of tools in organizational transformation. The conversation covers a range of topics including legacy applications and data, tools and change management, change adaptability and AI, culture of experimentation, guardrails and continuous planning, iterative model and systems thinking, AI documentation and institutional knowledge, continuous everything and business transformation, and relationship skills and human connection. The speakers discuss the importance of historical knowledge, building relationships, change management, experimentation, and the role of AI in simplifying and transforming business processes. They also emphasize the value of human connection and the role of AI in enhancing it. Takeaways Creating a culture of innovation and risk-taking is essential for IT and engineering teams. Measuring success with a customer focus and incentivizing innovation and risk-taking are key to driving organizational transformation. The importance of historical knowledge and relationships within an enterprise The value of continuous planning, implementation, and delivery Chapters 00:00 Introduction to Adrienne's Career 07:20 The Role of IT Leadership in Transformation 13:35 FOMO and FOBO in the Mid-Market Space 19:29 The Value of Trying New Things 26:38 The Role of Tools in Organizational Transformation 34:49 Tools and Change Management 40:42 Guardrails and Continuous Planning 47:36 AI Documentation and Institutional Knowledge 53:32 Continuous Everything and Business Transformation

6. 

   28 May 2026

   Jean Johnson discusses Ai in PE backed firms, strategic investment, and the seat at the big table

   The conversation covers a range of topics, including the importance of a multivariate background, understanding the language of the organization, balancing quick wins with long-term work, defining worthy projects and speaking CFO, time value of money and ROI challenges, balancing quick AI wins with long-term data governance and change management, customer impact, efficiency, and revenue as project criteria, and lessons learned from working with PE firms. The conversation delves into the strategic investment in AI, the importance of defending points of view, evaluating AI initiatives, shielding from polished vendor traps, earning a seat at the table, and coaching and understanding business seasons. Key takeaways include the significance of speaking CFO, building trust, and strategic IT leadership in the context of AI projects and IT leadership roles. Takeaways Multivariate background Understanding the language of other parts of the organization Balancing quick wins with long-term work Customer impact, efficiency, and revenue as project criteria Modeling behavior for others Nuances of speaking to a PE firm Speaking CFO Building Trust Strategic IT Leadership Chapters 00:00 Lessons Learned from Working with PE Firms 34:34 Strategic Investment in AI 40:08 Shielding from Polished Vendor Traps 51:23 Earning a Seat at the Table 01:02:09 Coaching and Understanding Business Seasons

7. 

   27 May 2026

   Ricki Koinig Discusses Human in the Loop, Watson, and Change Management for Ai Projects to Succeed

   Ricky Koenig, a CIO with extensive IT experience, discusses the importance of human involvement in technology, the challenges of AI implementation, and the significance of data readiness and governance for AI evolution. He shares his experience with IBM Watson and AI failures, highlighting the impact of Central European corporate culture on AI decision-making. The conversation delves into the critical themes of the role in the loop, misconceptions about AI roles, role evolution and organizational readiness, the shiny object problem, and leadership, human-centric approach, and organizational mindset. It emphasizes the importance of the right role at the right time, problem-centric approach, and the need for new blood and new ideas. Additionally, it highlights the danger of shiny object syndrome and the impact of organizational mindset on innovations. Takeaways Human involvement is crucial in technology projects Data readiness and governance are essential for successful AI evolution The importance of problem-centric approach in AI implementation The need for celebrating small wins and the danger of shiny object syndrome Chapters 00:00 Introduction to Ricky Koenig 05:41 Benefits and Misunderstandings of HCI and HIDL 13:47 The Significance of Innovation Maturity 18:54 The Impact of Idea Management on Innovation 25:14 The Role of Innovation Maturity in AI Readiness 35:19 Experience with IBM Watson and AI Failures 42:14 The Impact of Central European Corporate Culture on AI Decision-Making 55:28 Misconceptions About AI Roles 01:01:34 Role Evolution and Organizational Readiness 01:12:37 The Shiny Object Problem

8. 

   26 May 2026

   Vidhya Belapure Discusses the Future of the CIO and Why AI projects Succeed and Fail

   The conversation covers the evolution of the CIO role, emphasizing the shift from a service-oriented mandate to that of an advisor and strategic partner. It also highlights the importance of empathy in leadership, the challenges of AI implementation, and the talent gap in organizations. Additionally, it explores the building of a subject matter expertise team and the leadership skills required for the future CIO role. The conversation delves into the transition of CIOs to CEOs, the reasons behind AI project failures, success factors for AI projects, and the mid-market AI talent myth. It also explores the impact of AI on job roles and the importance of practical solutions over technology hype. The discussion emphasizes the need for a shift in mindset from technology solutions to problem-solving and the role of functional and institutional knowledge in AI projects. Takeaways Evolution of the CIO role Importance of empathy in leadership CIOs transitioning to CEOs AI project failures Leadership challenges in AI projects The impact of AI on job roles Chapters 00:00 Introduction and Career Background 05:29 The Role of Empathy in Leadership 20:19 AI Implementation and Talent Gap 30:02 Leadership Skills and Future CIO Role 35:38 CIOs Transitioning to CEOs 41:00 Success Factors for AI Projects

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