Asking Good Questions with Edward Roske

Edward Roske
  • 5.0 (1)
  • TECHNOLOGY

 In this podcast, we explore the CFO's office's past, present, and future, examining how technology and AI are transforming finance. Join Edward Roske and referents as they discuss innovative ways to enhance the role, optimize processes, and shape the future of financial leadership.  Designed for CFOs and finance leaders, each episode provides actionable insights into leveraging technology to drive growth, improve efficiency, and address challenges. With an engaging tone, the podcast simplifies complex concepts, covering topics like automating tasks, real-time data analysis, and strategic planning. Key themes include the shift from traditional finance methods to innovative, technology-driven processes and real-world examples like scenario modeling and automated reporting. The podcast also highlights future trends, such as generative AI for forecasting and advanced analytics for decision-making, promising to shape financial management. Edward Roske inspires listeners with practical advice and tools to embrace technology confidently. Tune in for strategies to thrive in the evolving financial landscape.

  1. 10/15/2025

    Zain Oke on Surviving a Corporate Crisis — and Selling to Chobani

    In this episode of Asking Good Questions, host Edward Roske sits down with Zain Oke, whose career reads like a masterclass in leadership, resilience, and strategic reinvention. From nearly two decades at Deloitte to the boardroom of Daily Harvest, and now leading automotive operations at AAA Northern California, Zain’s journey is a rare blend of financial discipline, operational innovation, and fearless transformation. The conversation begins with breaking news — Chobani’s acquisition of Daily Harvest — and dives into what it feels like to sit in the room when your company is being bought. Zain shares the inside view of how culture, values, and governance shape such decisions, and how companies can recover trust and rebuild momentum after public crises. They then explore the evolving relationship between AI and corporate oversight: how boards and audit committees should evaluate AI initiatives, separate game-changers from “expensive toys,” and build risk frameworks that keep innovation safe and accountable. Zain reveals how AI isn’t just reducing costs — it’s unlocking new possibilities for startups and scaling teams by lowering barriers to insight and automation. The discussion moves to the automotive future: from electric-vehicle repair pilots to the psychological barriers around autonomous cars. Zain candidly reflects on the balance between safety, public trust, and innovation, reminding listeners that AI’s biggest challenge may be the human fear of losing control. Finally, she offers invaluable advice for finance professionals: how to stay relevant as automation reshapes the CFO’s office, why governance experience is the new gold standard for board readiness, and why learning to “flow through data” is the key skill of the decade. If you care about finance, AI, corporate transformation, or the next wave of board leadership, this conversation will change how you see the intersection of business and technology. 💬 Quotes & Highlights “It’s not what happened — it’s what happens next.” “AI can be a force multiplier, not just a cost reducer.” “Boards don’t need more retired executives; they need active operators.” “Fear of losing control is at the heart of resistance to AI.” “Auditing teaches you how every part of a business actually works.” “Good information in, good information out — that never changes.” “We can’t stop what’s been unleashed, but we can help people trust it.” 🕒 Chapter Breakdown Intro – From Big 4 to Boardrooms (00:00–01:00) Chobani × Daily Harvest Deal (01:00–03:00) Recovering from Crisis & Rebuilding Trust (03:00–05:00) AI in the Boardroom: Guardrails & Governance (05:00–08:00) The Wellness Economy & Big-Brand Acquisitions (08:00–10:00) AI’s Impact on Finance & Operations (10:00–13:30) Digital Transformation in Automotive Services (14:00–17:00) Career Pivot: From Auditor to Operator (20:00–23:00) Balancing Board vs Operator Roles (24:00–26:00) Future of Finance & Automation (27:00–30:00) How to Join a Board (and Stay Relevant) (31:00–34:00) Lightning Round + Final Thoughts (34:00–39:00) This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

    40 min

  2. 10/01/2025

    From Oracle to AI Ops: Kellyn Gorman’s Playbook for Future-Proof Data Teams

    In this episode, Kellyn Gorman joins us for a candid conversation about what AI really means for data leaders, DBAs, and finance teams. From uncovering hidden bias in system defaults to rethinking how humans and AI collaborate, Kellyn lays out a roadmap that is both pragmatic and inspiring. If you’ve ever wondered whether AI will replace your role—or reshape it into something more impactful—this discussion is for you. Listeners will walk away with fresh insight into AI governance, the future of database engineering, and the leadership mindset needed to thrive in a rapidly changing landscape. Top Quotes “AI won’t replace deep specialists—it will demand they evolve.” “Bias doesn’t only exist in people; it’s baked into system defaults.” “Your job isn’t going away—it’s shifting to higher-value decision making.” “If you’re not questioning how your data is being used, you’re already behind.” “AI is a tool. How you lead with it is what creates advantage—or chaos.” Chapters Intro & Kellyn’s Journey — From Oracle DBA to AI thought leader AI Myths vs Reality — What AI changes, what stays the same The Bias Factor — How hidden defaults distort outcomes The Future of Database Work — DBAs, DevOps, and machine collaboration AI Governance — What leaders must prioritize right now Practical Playbook — Steps teams can take to future-proof their data ops Closing Thoughts — Kellyn’s advice to leaders navigating disruption This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

    41 min

  3. 09/17/2025

    The 4 P's of Finance Excellence: Mark Dendle Reveals His Secret Formula for Business Transformation

    Summary In this engaging conversation, Mark Dendle and Edward Roske explore the evolving landscape of finance, emphasizing the integration of AI, the importance of teamwork, and the common challenges faced across various industries. Mark shares his leadership philosophy, highlighting the significance of diversity and inclusivity in building effective teams. They discuss the critical role of data analytics and technology in driving business decisions and the future of finance as it adapts to new tools and methodologies. Mark's journey through different sectors showcases the transferable skills in finance and the necessity for continuous learning and adaptation in a rapidly changing environment. Takeaways AI is transforming finance, allowing for more efficient processes.Teamwork and diversity are essential for effective leadership.Financial skills are transferable across industries.Data analytics is crucial for informed decision-making.The role of CFO is evolving with technology integration.Continuous learning is necessary for career advancement.Understanding individual motivators is key to team success.Servant leadership fosters a supportive work environment.Project management is vital for successful transformations.Embracing change is essential in the finance sector.titles Navigating the Future of Finance with AIThe Power of Teamwork in Financial LeadershipSound Bites "The power of technology has really helped.""Vive la différence!""Have a great attitude, love learning."Chapters 00:00 The Excitement of AI Agents 05:47 The Philosophy of Teamwork 12:34 Common Financial Challenges Across Industries 22:02 The Four P's of Leadership 30:05 Cultural Influences and Personal Growth 35:42 Diversity of Thought and Paradoxical Thinking 41:01 The Evolution of Finance and AI Integration 49:32 The Future of Finance Careers and Skills This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

    42 min

  4. 09/03/2025

    Why Sipei Bowman Says Accountants Have the ‘Highest Pain Tolerance’ in Tech

    In this episode of "Asking Good Questions," host Edward Roske sits down with Sipei Bowman, a trailblazer in the realm of digital transformation within the finance sector. With over two decades of experience, Sipei has been at the forefront of revolutionizing financial systems at Jackson Square Aviation, overseeing assets exceeding $13 billion. Sipei recounts her journey from the early days of relying on Excel spreadsheets to spearheading the implementation of sophisticated ERP systems like Workday and Microsoft Business Central. She shares the challenges and triumphs of transitioning from traditional methods to embracing digital solutions that streamline operations and enhance decision-making processes. Listeners will gain insights into the strategic role of finance in today's fast-paced business environment, where real-time data and AI-driven analytics are becoming essential. Sipei discusses the importance of integrating technology with financial planning and analysis (FP&A) to become a strategic partner in business growth. This episode is a must-listen for finance professionals and business leaders eager to understand the impact of digital transformation on financial operations and the future of AI in finance. Tune in to explore how technology is reshaping the financial landscape and what it means for the future of financial leadership. Episode Highlights: Introduction to Digital Transformation in Finance Sipei Bowman's journey from Excel to ERP systems The role of AI in modern finance Challenges and successes in implementing digital solutions The strategic importance of FP&A in business growth Future trends in finance and technology Chapters: [00:00] Introduction Host Edward Roske introduces the topic and guest, Sipei Bowman. [02:15] Early Days of Finance Sipei shares her experiences starting with Excel and the initial challenges faced. [08:30] Embracing Digital Transformation Discussion on the transition to ERP systems and the impact on financial operations. [15:45] AI and Real-Time Analytics Insights into how AI is reshaping financial decision-making and operations. [22:00] Strategic Role of FP&A Exploring the evolving role of finance as a strategic business partner. [28:30] Future of Finance Predictions and trends for the future of finance and technology integration. [35:00] Conclusion Final thoughts and takeaways from Sipei Bowman. Subscribe to "Asking Good Questions" for more insights on business, technology, and financial leadership. This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

    52 min

  5. 08/20/2025

    From Silicon Valley to Ukraine Battlefields: Gauthier Vasseur Democratizes AI for 2,000+ Non-Coders

    oin Edward Roske and Gauthier Vasseur as they explore the democratization of AI, bridging the gap between academia and real-world applications. Discover how AI is transforming industries from Silicon Valley boardrooms to Ukrainian resilience efforts. Learn about the power of natural language coding and the importance of asking the right questions in data analytics. Key Topics: AI democratization and its global impact The role of AI in education and business Insights from Ukraine on practical AI deployment The future of AI: Natural language coding and no-code solutions Guest: Gauthier Vasseur, Executive Director of UC Berkeley's Fisher Center for Business Analytics and Co-President of the Alliance for Inclusive AI. Subscribe for more insights on AI and data analytics.  Share this episode with someone who needs to hear it! This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

    51 min

  6. 08/05/2025

    Why Dave Mitchell Says AI Will Replace Your CFO Before 2026 (And He's Not Wrong)

    In this episode of Asking Good Questions, host Edward Roske engages with finance expert Dave Mitchell, who shares insights from his extensive career spanning traditional accounting to digital media and consulting. They discuss the evolving relationship between technology and finance, the impact of AI on the finance sector, and the importance of trust and judgment in financial roles. Dave also reflects on his global travels and how they have shaped his perspective on finance and leadership. The conversation culminates in advice for future finance leaders, emphasizing the need for expertise and adaptability in a rapidly changing landscape. Takeaways The relationship between technology and finance has evolved significantly over the years.AI is transforming the finance sector, allowing for quicker access to information and analysis.Small companies can now compete at a higher level due to advancements in technology.Traveling globally can provide valuable insights into different business practices and cultures.Trust is essential in finance; over-reliance on technology can erode that trust.The judgment aspect of finance roles is still a human element that AI cannot replace.Future finance leaders should focus on developing expertise in specific areas.Working with entrepreneurs can provide a broader range of experiences and learning opportunities.The finance function is becoming more integrated with other business operations.AI can enhance efficiency but should be used with caution to maintain critical thinking.Sound Bites "Yahoo built the internet, right?""The judgment piece is still human.""Having a specialty makes you valuable."Chapters 00:00 Introduction to Financial Transformation 02:29 The Evolution of Technology in Finance 08:10 Shifts in Finance Perception 10:23 Technology Adoption in Small vs. Large Companies 15:30 Optimizing Resources in Startups 17:51 Global Perspectives on Finance 20:00 Life Lessons from Global Travel 28:08 The Future of Finance and AI 32:19 Disconnecting to Reconnect 34:12 Navigating Career Transitions 39:36 The Role of AI in Leadership 46:16 AI's Impact on Finance 51:30 Reflections on Travel and Culture 55:34 Advice for Future CFOs This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

    45 min

  7. 07/03/2025

    'I Got Tired of Cleaning Up Accounting Messes': How Kristen Berdar Turned Her Frustration Into a Multimillion-Dollar Business

    Summary In this episode of Asking Good Questions, Edward Roske interviews Kristen Berdar, a partner at BST and Company, who has pioneered virtual accounting solutions. They discuss the transformation of finance and accounting, the challenges of traditional models, and the impact of technology and AI on the industry. Kristen shares her journey in identifying market opportunities, overcoming resistance to change, and the importance of upskilling in the face of AI advancements. The conversation also touches on generational perspectives on virtual services, the significance of cloud technology, and the future of financial governance. Takeaways Kristen Berdar launched BST's virtual accounting solutions to address operational challenges in traditional accounting.COVID-19 accelerated the acceptance of remote accounting services.Younger generations are more receptive to hiring expertise remotely.Cloud technology is essential for modern accounting practices.AI can streamline processes but requires careful implementation to ensure data privacy.Financial governance can be enhanced through technology and multiple oversight layers.Integrating financial and non-financial data provides a comprehensive view for clients.Upskilling is crucial for finance professionals to adapt to AI advancements.Companies must balance daily operations with long-term technological goals.Building a strong peer network is vital for finance leaders. Sound bites "COVID excelled all of this" "AI can help them do that" "Find a really great peer group" Chapters 00:00 Introduction to Virtual Accounting Solutions 01:06 The Epiphany Behind Virtual Accounting 04:35 Overcoming Resistance to Change 06:22 Generational Shifts in Financial Services 08:59 Leveraging Global Resources for Client Success 11:54 Technology Integration in Accounting 15:03 Enhancing Financial Governance with Technology 16:35 Integrating Financial and Non-Financial Data 18:06 The Future of Accounting and AI 23:43 AI's Impact on the Accounting Profession 27:29 Balancing Daily Operations with Long-Term Goals 29:20 Lightning Round: Quick Insights This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

    33 min

  8. 06/16/2025 · BONUS

    Anna Tiomina's Bold Prediction: Finance Teams Will Be 'People and Robots' by 2030 - Part 3 of 3

    Summary In this conversation, the speakers discuss the future of finance in relation to AI, emphasizing the importance of interpersonal relationships and networking in a remote work environment. They explore the evolving roles of finance professionals, the impact of AI on entry-level positions, and the necessity for finance leaders to adapt to technological advancements while maintaining personal connections. Takeaways Building relationships is crucial for career advancement. AI will assist but not replace finance professionals. Networking should be a continuous effort, not just when job hunting. Remote work has made personal connections more challenging. Finance professionals need to adapt to AI and technology. There is a declining interest in finance careers among young people. AI can handle junior tasks, but mentorship is essential for growth. CFO roles will remain relevant despite AI advancements. Maintaining team dynamics is vital in finance roles. The future of finance will involve collaboration between humans and AI. Sound Bites "AI is not going to replace you there." "It's like picking your favorite child." Chapters 00:00 The Future of Finance and AI Skills 05:56 Building Relationships in a Remote World 12:04 The Evolving Role of Finance Professionals This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

    12 min
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 In this podcast, we explore the CFO's office's past, present, and future, examining how technology and AI are transforming finance. Join Edward Roske and referents as they discuss innovative ways to enhance the role, optimize processes, and shape the future of financial leadership.  Designed for CFOs and finance leaders, each episode provides actionable insights into leveraging technology to drive growth, improve efficiency, and address challenges. With an engaging tone, the podcast simplifies complex concepts, covering topics like automating tasks, real-time data analysis, and strategic planning. Key themes include the shift from traditional finance methods to innovative, technology-driven processes and real-world examples like scenario modeling and automated reporting. The podcast also highlights future trends, such as generative AI for forecasting and advanced analytics for decision-making, promising to shape financial management. Edward Roske inspires listeners with practical advice and tools to embrace technology confidently. Tune in for strategies to thrive in the evolving financial landscape.

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