Inside the CFO Office

This episode features Jason Wooten, Head of Finance Operations at ClickUp - a finance leader who has truly lived the evolution of Finance Ops.

With a career that spans business development, procurement, collections, deal desk, and enterprise transformations, Jason brings a unique cross-functional view to finance that’s rooted in operational grit and strategic thinking.

In this episode, "Finance Ops Leadership in a Digital World", we unpack:

🔹 Jason’s unconventional journey from cold-calling sales rep to leading Finance Ops at one of the most innovative SaaS companies

🔹 What it really takes to scale cash collections and balance logo vs. cash retention

🔹How Jason led a high-stakes office relocation project - sourcing off-market real estate and negotiating government incentives, the hardest but most rewarding project of his career

🔹 The tech transformation that reshaped finance-customer collaboration

🔹 His take on why the CFO tech stack is outdated and how AI can bring the biggest transformation

🔹 Tactical career advice for anyone aspiring to lead finance operations in the modern age

If you're building or leading finance operations in 2025 and beyond - this one’s packed with real talk, hard-won lessons, and honest reflections.

#InsideTheCFOOffice #Podcast #FinFloh #FinanceOps #CFO #CFOTech #SaaSFinance #AIinFinance #FinanceLeadership #ClickUp

This episode features Alex MacGillivray, VP Finance at Clio - one of the leading cloud-based legal tech firms globally. With a career spanning Deloitte, Easy Markit, and Clio, Alex’s journey is a masterclass in evolving from compliance to strategic leadership.

Since joining Clio in 2018, Alex has helped scale the finance org from 5 to 60+ people, led multiple acquisitions, and played a pivotal role in Clio’s record-breaking $900M Series F funding - the largest private tech financing in Canadian history.In this episode, titled “Controllers as Finance Leaders,” we explore how modern Controllers are becoming architects of strategy, culture, and growth.

Key Highlights:

1️⃣ From Audit to Impact - How Alex went from auditing silver mines and tribal governments to leading billion-dollar SaaS finance

2️⃣ Redefining Controllership - Why modern Controllers must go beyond accuracy to influence, storytelling, and business partnership

3️⃣ Tech at Scale - The challenges of scaling finance in a hypergrowth SaaS environment (including posting 6M+ journal entries/year!)

4️⃣ ERP Pain & AI Potential - Why today’s ERP systems are stuck in the past — and where AI could finally bridge the CFO tech gap

5️⃣ Values Drive Culture - How excellence, integrity, and empathy became the backbone of Alex’s leadership philosophy

💡 One of my favorite insights from the episode: “Your numbers don’t speak for themselves. The best Controllers help the business understand itself through the stories those numbers tell.”

A huge thank you to Alex for an inspiring conversation — packed with practical advice, deep reflection, and a clear vision for what finance leadership should look like in 2025 and beyond.

This episode features Jeff Pollack - a finance veteran whose career spans investment banking, capital markets, and blockchain innovation. Former CFO of IOHK and now Strategic Advisor to the Hoskinson Family Office, Jeff brings a rare blend of traditional financial discipline and future-facing tech insight.

In this episode titled “CFOs as Co-Pilots to CEOs,” we explore the evolving expectations from CFOs - from being the financial conscience to strategic business partners at the leadership table.

Key Highlights:

1️⃣ From Analyst to Advisor – Jeff’s journey from Wall Street to blockchain and the lessons that shaped his leadership

2️⃣ Speaking the CEO’s Language – How great CFOs focus on what matters and influence decisions that move the business

3️⃣ Fixing the CFOTech Gap – Why disconnected systems fail and how AI needs clean, connected data to deliver

4️⃣ People Over Platforms – Why finance teams need upskilling before tech can truly transform how they work

💡 One of the favorite takeaways from the episode:

“There’s nothing more powerful than the CEO turning to the CFO and saying - maybe you can help me with this business strategy.”

Huge thanks to Jeff for sharing his journey, insights, and forward-thinking lens on the modern CFO’s role. This episode is packed with grounded stories and sharp reflections - a must-listen for every finance leader navigating rapid change.

www.finfloh.com/podcast

This episode features Alexander J. Freeman, CFO at Wursta, and a global finance leader with 20+ years of experience across American Express, Visa, Dell Technologies, HID Global, and Diebold Nixdorf.

Alex has led finance transformations across markets - from New York and Moscow to Dubai and Austin. In this episode titled "The Fine Balance of a CFO Between Finance & Operations," we unpack the real-world realities of scaling finance in high-growth companies.

Here’s what we explore:

1️⃣ From Risk to Strategy - How Alex’s path from controllership to global finance helped him lead with adaptability

2️⃣ Scaling with People First - Lessons from maturing a finance org in a high-growth company, and why team structure matters

3️⃣ Finance + Ops Synergy - How understanding operations deeply helps finance leaders become true business partners

4️⃣ Modern CFOTech - Why it’s crucial to align tools to your business context and evaluate ROI upfront

5️⃣ AI for Finance - How Alex and his team are experimenting with Gemini and building AI fluency across functions

6️⃣ Advice for Future Leaders - Keep learning, stay open to unexpected opportunities, and don’t wait to lead

💡 Favourite lines from the conversation: “Great things often come from unexpected places - books, conversations, or mentors. Keep the doors open and stay curious.”

A huge thank you to Alex for sharing his journey, lessons, and forward-looking views. This episode is packed with grounded, practical insights - and a global lens that’s rare and refreshing.

Episode 12 features Scott Meyers, CFO & Corporate Secretary at Plurilock, a publicly listed cybersecurity firm. He is a seasoned finance leader with over 20 years of experience across cybersecurity, gaming, energy, and tech—and has a proven track record of leading transformations that deliver results, like achieving $2M in cost savings within 90 days.

In this episode, ‘Getting Financial Transformation Right: A CFO’s Perspective,’ we dive into:

1️⃣ CFO Transformation: What real transformation looks like from the CFO’s seat

2️⃣ Modern CFOTech: What today’s CFOs look for in a modern CFOTech stack

3️⃣ AI in Finance: How AI is evolving within the finance function

One of my favorite moments was Scott's analogy of the "golden age of finance tools," highlighting the abundance of new technologies available to finance leaders. It's a great perspective on the exciting times we're in!

A big thank you to Scott for sharing his valuable expertise and advice! This episode is a must-listen for CFOs, finance leaders, and anyone interested in the future of finance.

www.finfloh.com/podcast

#InsideTheCFOOffice #Podcast #FinFloh #FinanceLeadership #CFO #FinanceTransformation #CFOTech #AIinFinance

The Episode 11 podcast with Gary Lu, CFO, Biomerica focuses on ‘CFO Leadership at Public Firms: Strategy, Scale & AI’. We explore how CFOs aren’t just responsible for numbers—they’re managing investor expectations, navigating compliance, and embracing AI and automation to stay ahead.

🚀 Key takeaways from the episode:

1️⃣ CFOs as Strategic Leaders – The modern CFO’s role goes far beyond financial reporting. Gary shares how today’s finance leaders must balance growth, compliance, and operational efficiency, while also driving technology adoption and business strategy.

2️⃣ Public vs. Startup Finance – The difference isn’t just about size. Public companies require strict regulatory compliance and investor relations, while startups demand agility and risk-taking. The best CFOs understand how to blend both mindsets to drive success.

3️⃣ AI is changing the game—but only for those who embrace it – From real-time financial insights to predictive analytics, AI is making CFOs more proactive and data-driven than ever before.

One of my favorite moments from this conversation? Gary’s take on how traditional ERPs, while powerful, can be costly and time-consuming to implement, often requiring extensive customization and resources. In contrast, modern SaaS solutions bring flexibility, faster deployment, and lower costs, making it easier for finance teams to adapt and scale without the complexities of legacy systems.

A huge thank you to Gary for this insightful discussion! If you’re a CFO, finance leader, or just passionate about where finance is headed, this episode is a must-listen.

In Episode 10 – The Evolving Role of CFOs in Fintech Firms, we explored how CFOs navigate financial strategy across different environments—startups vs. enterprises—and what the future of finance tech holds. If you're curious about the evolving CFO role and the next wave of financial innovation, this episode is packed with insights.

A few key takeaways:

1️⃣ CFOs as Strategic Co-Pilots – The modern CFO isn’t just a numbers person. Subodh shared how CFOs must balance growth ambitions with financial sustainability and risk, acting as key advisors to the CEO and driving long-term business success.

2️⃣ Startups vs. Enterprises – What’s different? Large corporations prioritize stability and scale, leveraging structure and resources for sustained growth. Startups, meanwhile, thrive on agility and bold execution, turning high-risk bets into industry-changing innovations. Subodh’s insights reveal how both paths offer unique challenges—one builds legacies, the other reshapes industries at speed.

3️⃣ AI’s Role in Finance – AI isn’t just hype; it’s already reshaping finance through predictive analytics, credit risk assessment, accounts receivable automation, pricing models, and compliance automation. But we’re only scratching the surface of its full potential.

4️⃣ Career Growth in Finance – There’s no single path to becoming a CFO—whether through corporate finance, investment banking, or startups—but the key skills remain the same: deep financial expertise, strong storytelling, and the ability to enable business growth.

The standout moment was Subodh’s perspective on why today’s ERP and financial systems need to evolve beyond data collection and reporting, and embrace automation, intelligence, and predictive capabilities.

Finance leaders can’t afford to rely solely on historical data—they need real-time insights and forward-looking strategies to stay ahead.

A huge thank you to Subodh for sharing his expertise, experiences, and candid insights! If you’re in finance, fintech, or leadership, you won’t want to miss this one.

If you’ve ever wondered what it takes to lead finance at a global AI-first tech giant (or how to pivot from investment banking to CFO!), this podcast episode is packed with golden nuggets.

A few highlights from the episode:

1️⃣ The “CFO evolution”: Marc shared how the role has shifted from being a “numbers guardian” to a strategic co-pilot, especially in hyper-growth tech. Spoiler: It’s less about spreadsheets and more about strategic thinking, cross-functional alignment, and anticipating market shifts before they happen.

2️⃣ AI in finance – more than just automation: At InMobi, AI isn’t just a tool—it’s embedded into their financial strategy. But Marc made one thing clear: AI isn’t a magic fix. Without strong data infrastructure and optimized processes, even the best AI models fall short. He also shared why agentic AI—AI that can autonomously interact with external systems—could redefine finance in the years to come.

3️⃣ Leading teams across cultures: Having built finance teams in both the U.S. and India, Marc’s insights on bridging communication styles, decision-making rhythms, and even meeting dynamics were pure gold for global leaders.

One thing that stood out? Marc’s take on the “80/20 problem” in finance—how teams spend too much time on edge cases and routine tasks instead of driving real impact. His vision? Let AI handle the busywork so finance professionals can focus on the big, strategic decisions that actually move the needle.

Jon Gross, CFO at RepeatMD, with over 15 years of experience in finance and operations leadership has an impressive career that spans across industries like healthcare, technology, and venture-backed startups. From driving financial strategy at Mile High Labs to leading operational excellence at Keen and Redesign Health, Jon has consistently demonstrated expertise in scaling businesses, optimizing processes, and delivering impactful results.

Chris McCourt, CFO at Bergmeyer, brings over two decades of finance leadership across industries like technology, advertising, and real estate. He’s known for driving strategic growth, mastering P&L, M&A, and optimizing cash flow. His experience leading firms like Digilant, VaultLogix, and others highlights his expertise in financial transparency, risk management, and team performance.

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