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GrowCFO Show

Kevin Appleby
GrowCFO Show
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  • #258 From Controller to CFO: The Playbook Behind CSAA’s Transformation, Andrea Hecht, Chief Financial Officer, CSAA Insurance Group
    https://www.youtube.com/watch?v=qZ4_Fr3a07Y .entry-img img{ display:none !important; } .single .hentry .entry-img{ display:none !important; } https://open.spotify.com/episode/1FpRXhcwICZELr5lwHBodV In this episode, host Kevin Appleby speaks with Andrea Hecht, Chief Financial Officer at CSAA Insurance Group, to explore the realities of leading finance within a member-owned insurance organisation. The conversation traces Andrea’s professional evolution—from a Midwest-based controller with a public-accounting background to a strategic CFO steering one of the nation’s major property and casualty insurers. Andrea shares how transitioning from controller to CFO required developing a deep strategic lens, embracing enterprise-wide business partnering, and cultivating confidence to challenge executive consensus. She also discusses the complexities of the insurance sector—from pricing uncertainty and catastrophe risk to regulatory constraints—and how technology, data, and AI are reshaping financial planning and claims management. Her story offers a practical playbook for finance leaders ready to elevate their impact beyond accounting into organisational leadership. Key topics covered: Andrea’s career journey from EY auditor in Ohio to CFO of CSAA Insurance Group in California. Why the CFO role demands strategic thinking that connects company vision with financial planning and resource allocation. The unique financial challenges of the insurance industry—pricing risk without knowing true costs for years, managing reinsurance markets, and handling catastrophe losses. How membership ownership changes financial priorities versus shareholder-driven models, placing policyholders at the centre. The importance of financial education and business partnering to build trust across departments and improve decision quality. How AI and automation are transforming finance, forecasting, and claims—bringing speed, empathy, and new skill-building challenges for future talent. Links Andrea Hecht on LinkedIn Kevin Appleby on LinkedIn GrowCFO Mentoring Timestamps 00:28 Andrea’s background and move from Ohio to California 03:30 Inside CSAA Insurance Group: business model and coverage areas 05:00 Challenges of pricing insurance and managing capital risk 12:40 Transition from controller to CFO—learning to think strategically 16:10 Building finance partnerships and educating the organisation 18:10 Balancing collaboration and contrarian thinking with the CEO 25:00 Forecasting amid inflation and market volatility 27:35 How AI and generative tools are redefining productivity 34:00 Future of work, training paths, and ethical concerns in AI adoption 36:35 What CFOs should know about the changing insurance landscape Find out more about GrowCFO If you enjoyed this podcast, you can subscribe to the GrowCFO Show with your favorite podcast app. The GrowCFO show is listed in the Apple podcast directory, Spotify and many others. Why not subscribe there today? That way, you never miss an episode. GrowCFO is a great place to extend your professional network. Join GrowCFO as a free member today and participate in our regular networking events and webinars. Premium members can also access our extensive training center and CFO Digital Toolkit. You can enroll in our flagship Future CFO or Finance Leader programs here. You can find out more and join today at growcfo.net
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  • #257 The Three Hidden Traps That Stall New CFOs, Michael O’Reilly, GrowCFO Executive Coach
    https://www.youtube.com/watch?v=FyOBP_QcsLI .entry-img img{ display:none !important; } .single .hentry .entry-img{ display:none !important; } https://open.spotify.com/episode/3CrRco4GBJsnDQYaJSiPnT In this insightful episode, Kevin Appleby sits down with Michael O’Reilly, a seasoned executive coach and former CFO with a diverse career spanning global finance, digital transformation, and leadership development. Together, they explore “The Three Hidden Traps That Stall New CFOs” — a candid discussion about the unseen challenges finance leaders face as they transition into enterprise leadership roles. Michael shares his own experiences across companies like Citibank, Gap Inc., and PepsiCo, highlighting how curiosity, empowerment, and trust play crucial roles in a CFO’s success. He also explains how imposter syndrome, reluctance to delegate, and overreliance on technical mastery can prevent new CFOs from thriving in their roles. With AI reshaping the finance landscape, Michael emphasises the growing importance of emotional intelligence, adaptability, and creating psychological safety for teams navigating disruption. The conversation goes beyond professional growth, touching on personal fulfilment and energy management — understanding what “charges or drains your batteries” as a leader. Drawing from his coaching practice and experiential leadership retreats in Ireland, Michael reveals how rediscovering purpose and flow can reignite a CFO’s impact, both in business and in life. Key topics covered: How imposter syndrome can fuel curiosity and growth rather than paralysis Why delegating and letting go is the biggest unlock for new CFOs The importance of psychological safety in driving innovation and AI adoption Transitioning from technical expert to strategic enterprise leader Understanding personal “energy management” to avoid burnout The power of trust, empathy, and soft skills in effective CFO leadership Links Michael O’Reilly on LinkedIn Kevin Appleby on LinkedIn GrowCFO Mentoring Timestamps 00:40 Michael O’Reilly’s career journey from CPA to Chief Digital Officer 05:52 The role of imposter syndrome in a CFO’s development 07:52 How AI amplifies insecurity and why creating safe environments matters 10:07 Balancing accuracy with experimentation in finance leadership 16:46 What a mentoring relationship looks like with Michael 21:21 The critical need to delegate and empower teams 22:33 Michael’s experiential leadership program in Ireland 30:31 Finding your “flow state” and energizers outside of work 34:20 What kind of leaders benefit most from mentoring 36:16 The “ski story” — how aligning passion with leadership drives performance Find out more about GrowCFO If you enjoyed this podcast, you can subscribe to the GrowCFO Show with your favorite podcast app. The GrowCFO show is listed in the Apple podcast directory, Spotify and many others. Why not subscribe there today? That way, you never miss an episode. GrowCFO is a great place to extend your professional network. Join GrowCFO as a free member today and participate in our regular networking events and webinars. Premium members can also access our extensive training center and CFO Digital Toolkit. You can enroll in our flagship Future CFO or Finance Leader programs here. You can find out more and join today at growcfo.net
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  • #256 The CFO Guide to AI Hype: What To Do First, Hannah Munro, Managing Director, ITAS Solutions
    https://www.youtube.com/watch?v=mg1knQ7TQ_E .entry-img img{ display:none !important; } .single .hentry .entry-img{ display:none !important; } Artificial Intelligence continues to dominate finance discussions, but for many CFOs, the real challenge isn’t understanding the technology—it’s knowing where to start. In this episode, host Kevin Appleby welcomes back Hannah Munro, Managing Director of ITAS Solutions and host of the CFO 4.0 Podcast, to unpack the hype surrounding AI and offer clear, practical steps for finance leaders ready to take action. Hannah shares first-hand insights from her work helping finance teams implement technology-driven transformations, explaining why success depends less on the AI tools themselves and more on simplifying processes, standardizing data, and fostering cultural change. The conversation draws a clear distinction between technology implementation and true transformation—and why CFOs must master both to realise measurable ROI from new systems. As AI continues to evolve at an unprecedented pace, Hannah and Kevin explore how finance leaders can stay agile, focus on data quality, and ensure their organizations are prepared for the next generation of AI-enabled finance. From managing expectations to defining tangible outcomes, this episode is an essential listen for CFOs looking to move beyond buzzwords and deliver meaningful digital transformation. Key topics covered: The difference between AI-enabled tools and building AI from scratch—and why most finance teams are already using AI without realising it. Why the biggest implementation risks aren’t technical but cultural and process-related. How to distinguish transformation from implementation—and why most projects should involve both. The importance of defining measurable outcomes before investing in technology. Why simplification, standardisation, and clean data are the foundations for any successful AI adoption. How CFOs can future-proof their finance function by focusing on integration, agility, and benefit-driven technology selection. Links Hannah Munro on LinkedIn Kevin Appleby on LinkedIn GrowCFO Mentoring Timestamps 01:00 Why AI isn’t new—and how finance teams are already using it unknowingly 03:25 Implementation vs. transformation: the fundamental question every CFO must ask 07:30 Why traditional RFP processes often fail in fast-changing tech environments 10:45 The hidden cost of customisation and how to challenge unnecessary complexity 16:15 Measuring the true value and ROI of finance technology projects 19:20 Why every tech implementation should also be a transformation initiative 27:20 Using psychology and “nudging” principles to drive behavioural change in transformation 33:30 Preparing for AI: simplify processes, integrate systems, and clean your data 38:40 The limits of AI: understanding data quality, context, and validation 44:30 Looking ahead—how AI, automation, and integration will redefine the finance function Find out more about GrowCFO If you enjoyed this podcast, you can subscribe to the GrowCFO Show with your favorite podcast app. The GrowCFO show is listed in the Apple podcast directory, Spotify and many others. Why not subscribe there today? That way, you never miss an episode. GrowCFO is a great place to extend your professional network. Join GrowCFO as a free member today and participate in our regular networking events and webinars. Premium members can also access our extensive training center and CFO Digital Toolkit. You can enroll in our flagship Future CFO or Finance Leader programs here. You can find out more and join today at growcfo.net
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  • #255 From CFO to CEO: Lessons on Leadership, Dave Osh, Mentor
    https://www.youtube.com/watch?v=xOotp0bZAdU .entry-img img{ display:none !important; } .single .hentry .entry-img{ display:none !important; } https://open.spotify.com/episode/3CrRco4GBJsnDQYaJSiPnT In today’s rapidly evolving business environment, the transition from CFO to CEO is a journey that demands more than technical expertise—it requires a profound shift in mindset, leadership style, and strategic vision. In this episode, Dave Osh, a seasoned CFO, CEO, and mentor, joins host Kevin Appleby to share his unique path from fighter pilot to corporate leader, and the critical lessons learned along the way. The episode opens by underscoring the importance of leadership agility and the ability to adapt to new domains, stakeholder dynamics, and the ever-changing demands of the C-suite. Dave Osh discusses the challenges CFOs face when stepping into broader leadership roles, emphasizing the need for executive presence, effective communication, and a deep understanding of both business strategy and human psychology. He introduces his “CFO aura” framework—openness, unattached perspective, resonance, and authenticity—as essential qualities for finance leaders aspiring to become strategic collaborators and inspirational CEOs. Drawing from his books and real-world experiences, Dave provides actionable insights for finance professionals seeking to unlock their leadership potential and drive meaningful change within their organizations. Key topics covered: The journey from CFO to CEO requires a shift from technical mastery to strategic leadership Executive presence and effective communication are critical for C-suite success The “CFO aura” framework: openness, unattached perspective, resonance, authenticity Navigating stakeholder relationships and organizational politics is essential Continuous learning and personal development underpin leadership growth Playfulness and joy can empower leaders and foster a positive work culture Links Dave Osh on LinkedIn Kevin Appleby on LinkedIn GrowCFO Mentoring Timestamps 0:02:07 Dave Osh’s unique journey from fighter pilot to CFO and CEO 0:05:29 Challenges and learning curves in becoming a CFO 0:10:43 Developing executive presence and the “CFO aura” framework 0:15:28 Practical advice for CFOs to avoid being seen as a naysayer 0:20:04 Transition from CFO to CEO and lessons on leadership philosophy 0:30:15 Dave’s books and frameworks for leadership development 0:38:35 The role of playfulness and joy in effective leadership Find out more about GrowCFO If you enjoyed this podcast, you can subscribe to the GrowCFO Show with your favorite podcast app. The GrowCFO show is listed in the Apple podcast directory, Spotify and many others. Why not subscribe there today? That way, you never miss an episode. GrowCFO is a great place to extend your professional network. Join GrowCFO as a free member today and participate in our regular networking events and webinars. Premium members can also access our extensive training center and CFO Digital Toolkit. You can enroll in our flagship Future CFO or Finance Leader programs here. You can find out more and join today at growcfo.net
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  • #254 Why “Fractional CFO” Isn’t What You Should Be Selling James Donovan, Founder, Nine Two Media
    https://www.youtube.com/watch?v=H4pb1S_bdgE .entry-img img{ display:none !important; } .single .hentry .entry-img{ display:none !important; } https://open.spotify.com/episode/4QIAi3e2eHEp57xjU474IH In today’s competitive financial services landscape, simply offering “fractional CFO” services is no longer enough to stand out or win business. In this episode, James Donovan, Founder of Nine Two Media, joins host Kevin Appleby to challenge the conventional approach to selling CFO services. The conversation opens by emphasizing that business owners rarely seek out a “fractional CFO” by name; instead, they are looking for solutions to pressing problems—especially those that keep them up at night, like cash flow and financial clarity. Donovan shares insights from his experience helping accounting firms and CFOs shift their marketing from generic service offerings to problem-solving, value-driven messaging. He explains why focusing on the client’s pain points, leveraging digital marketing channels like LinkedIn and Facebook, and building authority through content and podcasting are essential for growth. The episode offers actionable strategies for finance professionals to reposition themselves as indispensable advisors, not just another service provider. Key topics covered: Business owners buy solutions to problems, not “fractional CFO” services Effective marketing focuses on client pain points, not credentials or titles LinkedIn and Facebook are key channels for building authority and generating leads Relying solely on referrals is not a sustainable marketing strategy Podcasting and content creation help establish credibility and reach new audiences Case studies and client success stories are powerful tools for differentiation Links James Donovan on LinkedIn Kevin Appleby on LinkedIn GrowCFO Mentoring Timestamps 0:05:00 Trends in the fractional CFO market and the shift toward advisory roles 0:07:55 Why selling “fractional CFO” services misses the mark—focus on solving business problems 0:11:16 Digital marketing strategies: LinkedIn and Facebook for lead generation 0:17:15 The role of websites and content in attracting clients 0:22:07 The need for proactive marketing and moving beyond referrals 0:24:03 Podcasting as a tool for authority and business development Find out more about GrowCFO If you enjoyed this podcast, you can subscribe to the GrowCFO Show with your favorite podcast app. The GrowCFO show is listed in the Apple podcast directory, Spotify and many others. Why not subscribe there today? That way, you never miss an episode. GrowCFO is a great place to extend your professional network. Join GrowCFO as a free member today and participate in our regular networking events and webinars. Premium members can also access our extensive training center and CFO Digital Toolkit. You can enroll in our flagship Future CFO or Finance Leader programs here. You can find out more and join today at growcfo.net
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