Enterprise Signals

Tom Welke and Richard Doran
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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

Episodes

  1. Aug 12

    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-inThe role of the CIO is evolving from service provider to internal consultant and advocateData readiness and standardization are crucial for successful AI initiativesCollaboration and strategic planning are essential for aligning IT initiatives with business goalsA third party can facilitate alignment and create a cohesive AI roadmap Chapters 00:00 Inflection Points in AI Pilots30:16 Framing and Planning AI Pilots33:01 The Evolving Role of the CIO43:02 The Significance of Data Readiness49:25 Collaboration and Strategic Planning in IT Initiatives53:23 The Role of a Third Party in Facilitating Alignment

  2. Aug 6

    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 toolboxImportance of governance and guardrails in AI implementation Governance of AI tools is crucialCustomer experience is a key differentiatorActive listening and alignment with business requirements are essential for success Chapters 00:00 Introduction to AI in the Mid-Market Space02:03 The Role of Hackathons in AI Momentum03:02 AI as a Tool in the Toolbox07:16 Leadership Insights and Agile Approach11:13 Lessons from GE and Transformational Organizations34:00 The Importance of Governance and Guardrails in AI38:25 The Chasing of the Shiny Object39:24 Leadership and the End Game41:08 Center of Excellence and Shadow IT50:03 Building Trust and Communication01:09:19 Customer Experience and Business Alignment

  3. Aug 4

    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 contextEvaluating AI project presentations requires a focus on the real meat of the projectThe 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 Challenge01:46 The Length of Projects and Enthusiasm03:37 The Impact of Digital Transformation07:29 Data Quality and AI10:01 Synthetic Data and Its Implications13:40 Forecasting and AI17:04 Team Composition for AI Projects21:20 The PMBA Combo and Its Importance26:38 Knowing When to Quit an AI Project29:23 Becoming an Advisor to the C-Suite30:48 Presenting Ideas and Status in Context32:11 Articulating the Request and Status33:07 Elevating the Conversation from IT as a Utility34:45 Evaluating AI Project Presentations36:27 Challenges of AI Project ROI40:22 The Impact of AI on Staffing and Institutional Knowledge43:02 Total Cost of Ownership and People Side of Efficiency50:21 Pressure to Control Head Count with AI52:43 The Importance of Redundancy and People Side of Efficiency56:00 The Future of Conversations on AI and Business Projects

  4. Aug 4

    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 AutomationOrganizational Change ManagementHuman in the LoopRole Evolution AI Expertise CautionDomain Knowledge Importance Chapters 00:00 The Role of Auditors in Innovation02:46 The Misconception of AI Tools05:09 Starting the AI Journey13:16 The Importance of Change Management18:29 Human in the Loop and Role Evolution26:12 The Danger of Cutting Expert Roles28:50 Rebranding as AI Expert30:17 Understanding Business Needs31:35 Hiring for Adaptability36:37 Recruitment Criteria and Innovation Framework45:24 Organizational Change Management49:04 Earning a Seat at the Table53:22 Balancing Innovation and Building Blocks

  5. Jun 17

    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 enterpriseThe value of continuous planning, implementation, and delivery Chapters 00:00 Introduction to Adrienne's Career07:20 The Role of IT Leadership in Transformation13:35 FOMO and FOBO in the Mid-Market Space19:29 The Value of Trying New Things26:38 The Role of Tools in Organizational Transformation34:49 Tools and Change Management40:42 Guardrails and Continuous Planning47:36 AI Documentation and Institutional Knowledge53:32 Continuous Everything and Business Transformation

  6. May 28

    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 backgroundUnderstanding the language of other parts of the organizationBalancing quick wins with long-term workCustomer impact, efficiency, and revenue as project criteriaModeling behavior for othersNuances of speaking to a PE firm Speaking CFOBuilding TrustStrategic IT Leadership Chapters 00:00 Lessons Learned from Working with PE Firms34:34 Strategic Investment in AI40:08 Shielding from Polished Vendor Traps51:23 Earning a Seat at the Table01:02:09 Coaching and Understanding Business Seasons

  7. May 27

    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 projectsData readiness and governance are essential for successful AI evolution The importance of problem-centric approach in AI implementationThe need for celebrating small wins and the danger of shiny object syndrome Chapters 00:00 Introduction to Ricky Koenig05:41 Benefits and Misunderstandings of HCI and HIDL13:47 The Significance of Innovation Maturity18:54 The Impact of Idea Management on Innovation25:14 The Role of Innovation Maturity in AI Readiness35:19 Experience with IBM Watson and AI Failures42:14 The Impact of Central European Corporate Culture on AI Decision-Making55:28 Misconceptions About AI Roles01:01:34 Role Evolution and Organizational Readiness01:12:37 The Shiny Object Problem

  8. May 26

    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 roleImportance of empathy in leadership CIOs transitioning to CEOsAI project failuresLeadership challenges in AI projectsThe impact of AI on job roles Chapters 00:00 Introduction and Career Background05:29 The Role of Empathy in Leadership20:19 AI Implementation and Talent Gap30:02 Leadership Skills and Future CIO Role35:38 CIOs Transitioning to CEOs41:00 Success Factors for AI Projects

  • 8 Episodes

About

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

Information

  • Creator
    Tom Welke and Richard Doran
  • Years Active
    2026
  • Episodes
    8
  • Rating
    Clean
  • Copyright
    © 2026 Tom Welke and Richard Doran
  • Show Website
    Enterprise Signals