Tom is joined by Evan Campbell, author of Adapt to Win, to explore why strategy so often fails in execution. Evan explains how strategy decay, organizational inertia, artificial precision in budgeting, and excess work in process prevent companies from adapting and investing effectively. He discusses the CFO’s role in aligning capital with strategic outcomes, using OKRs to create vertical and horizontal alignment, and applying venture capital principles to fund, evaluate, and stop initiatives. Evan also shares lessons from his experience as an Airborne Ranger and Green Beret on empowered leadership, command intent, and building organizational capability. Finally, he reflects on reinvention across his career in the military, technology, consulting, authorship, and ranch life.

Guest quotes:
“ All of the day-to-day chaos of the marketplace and the sales pipeline and all the emergencies and noise in the organization and conflicting priorities and goals of everybody in the organization drowns out the strategic signal of leaders' intent. And leaders have to put energy into the system to keep the clarity of that signal above the noise.”

“If your strategy has any creativity or innovativeness or significant growth objectives in it, you have to force the organization to make that change. The CFO is crucially important in both getting that strategic message through and getting things moving in a new direction.”

“Because we didn't deploy the strategy with clarity, we don't have that steel thread of objectives and measures that allows us to show that we're making the right investment decision. You fall behind competitively because you're not funding innovation or things that are disruptive or drive competitive advantage.”

Links & Resources:

Connect with Tom Gavaghan

Connect with Evan Campbell

Learn more about Kyriba

Read Adapt to Win

YouTube Timestamps:

00:00 Show Intro and Guest Overview

04:09 When does strategy become an investment allocation decision?

07:26 The CFO’s role: why agility and control aren’t opposites

09:17 Strategy decay: why execution is so hard to get right

12:25 Spotting decay early: strategy deployment and execution governance

16:04 Funding long-term bets that lack short-term ROI

19:29 Measuring the unquantifiable with OKRs

22:22 The killer feature of OKRs: horizontal alignment

24:57 Making trade-offs and knowing your true capacity

27:42 Killing zombie projects: creating a culture where stopping is a good thing

31:40 Moving beyond the traditional budget: lean portfolio management

34:50 How leaders know when it’s time to change strategy

37:47 Leadership lessons from his time as an Airborne Ranger and Green Beret

42:15 Where to find Evan Campbell and closing thoughts

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Tom is joined by Cruz Gamboa, a 25-year Fortune 500 finance veteran turned fractional CFO and founder of Ascend Growth Ventures and ScalingCFO.io. Cruz explains why “just grow sales” becomes dangerous as companies scale, how the “cash void” can hide liquidity problems behind a healthy P&L, and why management teams must identify their biggest constraint before pushing for more growth. He also discusses the core financial practices every founder-led company needs, whether AI can replace the CFO, and why judgment, leadership, communication, and storytelling will matter more than ever. Finally, Cruz reflects on golden handcuffs, career identity, and knowing when it is time to make a change.

Guest quotes:
"When you scale chaos, chaos scales."

“Golden handcuffs are psychological, not just financial.  If we hate our jobs, if we hate our reality, if we hate our situation that we're in, we have two options. We either reframe in the way that we see what we do or we make a change.”

“ When you change the way you look at things, the things that you look at change. This is quantum physics.”

Links & Resources:

Connect with Tom Gavaghan

Connect with Cruz Gamboa

Learn more about Kyriba

Learn more about Ascend Growth Ventures

Learn more about ScalingCFO.io

YouTube Timestamps:

00:00 Show Intro and Guest Overview

02:22 The "cash void": when "just sell more" becomes bad advice

04:58 Where cash actually hides: the operating vs. liquidity business

08:20 "When you scale chaos, chaos scales"

09:39 What has to be true structurally before pulling the growth lever

13:20 The theory of constraints: finding the business's real bottleneck

15:56 Can AI replace the CFO?

20:23 Advice for young finance professionals in the AI era

22:58 Productizing ScalingCFO: checklist-driven client methodology

27:15 Why CFOs get left off the table: leadership and ego

31:12 The #1 CFO differentiator: soft skills and communication

33:16 Leaving too late: golden handcuffs and knowing when to go

40:30 What resonates most with his 30,000+ newsletter subscribers

42:47 Book recommendation: Think and Grow Rich by Napoleon Hill

44:12 Where to find Cruz Gamboa and closing thoughts

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Tom is joined by Patrick Villanova, CFO of BlackLine. Patrick shares how his path through 15 years at PwC and BlackLine's own controllership shaped his accountant's-eye view of risk, and how that background informs everything from platform strategy to M&A. Patrick digs into the real math behind build-versus-buy decisions, why private company valuations still haven't caught down to depressed public multiples, and why he's convinced this disconnect can't last. He also explains how BlackLine is deploying AI agents cautiously and deliberately — keeping a human in the loop at every step — and why that same "lean in, but verify" mindset is exactly what he'd tell any accountant or CFO trying to future-proof their career.

Guest quotes:
“ With any technological disruption, there are winners and losers. Those companies that avoided it or were afraid of it or didn't believe it, most of them went the way of the dinosaur.”

“Trust is something that takes years to build up and a nanosecond to destroy. We're bringing our customers along, building that trust, giving them a sampling, and then once we've established that, you have the S-curve of adoption that we've seen multiple times in history.”

“ The more diverse opinions you can get from a talent perspective within your culture, within your organization, the stronger your ultimate product and platform will be.”

Links & Resources:

Connect with Tom Gavaghan

Connect with Patrick Villanova

Learn more about Kyriba

Learn more about BlackLine

YouTube Timestamps:

00:00 Show Intro and Guest Overview

01:05 Patrick's background: BlackLine, PwC, accounting roots

02:03 BlackLine's evolution beyond financial close

03:19 Studio360 as the connective data layer

04:43 Single data source as the key to safe AI agents

05:32 Point solution perception vs. broader platform value

08:34 Why BlackLine stays ERP-agnostic

09:35 The BlackLine-Kyriba partnership model

12:24 Build vs. buy: weighing cost, speed, and talent

15:22 Why private valuations remain disconnected from public multiples

17:46 Engineering productivity gains from AI at BlackLine

19:10 Why "just build it" often underestimates true cost of ownership

23:22 Multiples: 2021 peak to the post-AI-narrative reset

26:53 The reckoning over real AI token costs

30:53 Balancing AI speed with accuracy and trust

34:35 Building customer trust through gradual AI adoption

36:07 Advice for CFOs resistant to change

39:38 Why evaluating security and partnerships matters as much as software

41:20 Advice for young finance professionals in the AI era

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Tom is joined by Kartik Kaushik, Managing Director and Head of RBC Clear. Kartik shares how he went from building India's first e-commerce platform at Unilever to reimagining corporate transaction banking in the US — and why that unconventional path gave him the customer advocate lens the industry desperately needed. He breaks down why corporate onboarding still takes 45 to 60 days, what it took to compress that to same-day, and how parallel processing and intelligent validation replaced an army of operations staff. Kartik also explains why he rebuilt RBC Clear as fully cloud-native from day one, how co-developing the platform with 28 of their largest clients shaped every product decision, and why the real unlock for treasury isn't just better technology.

Guest quotes:
“ Technology is only as good or as valuable as what the business case or the business intent or the need that you're solving for.”

“ You have to rethink policy, you have to rethink process, you have to rethink everything that's sacrosanct or held as the gold standard in the past. Everything has to be questioned.”

“ All the great products, we become part of their life as a customer, and the customer forgets we exist. That is the best state of any product.”

Links & Resources:

Connect with Tom Gavaghan

Connect with Kartik Kaushik

Learn more about Kyriba

Learn more about RBC Clear

YouTube Timestamps:

00:00 Show Intro and Guest Overview

00:26 Kartik's Background

01:44 Building the First E-Commerce Platform in India (1999–2000)

03:17 From Unilever to Citi to RBC

04:28 The Customer Advocate Lens in Corporate Banking

06:23 What Is RBC Clear? Putting Clients in Control of Working Capital

07:27 Co-Developing with 28 Client Advisory Firms

08:42 Why US Corporate Banking Is So Archaic

12:38 Re-Imagining Onboarding: From 67 Days to Same-Day

14:10 Time and Motion Study: The File Was Touched for Only 10.5 Hours

16:50 Pre-Populating Client Data and Intelligent Document Validation

19:58 Parallel Processing: How RBC Eliminated Sequential Handoffs

22:00 Pricing Transparency: Why Bank Invoices Require a PhD to Read

27:46 Flipping from Reactive to Proactive: The "Where Is My Payment?" Problem

29:20 No Published 1-800 Number: Zero Client-Facing Ops After 24 Months

32:14 What Had to Break Internally to Achieve Same-Day Onboarding

37:13 First Fully Cloud-Native Core Banking Payments Business

42:01 Lessons from Unilever: Start with the "So What"

43:50 The Three Types of Workers in an Agentic AI World

49:25 Outro and Wrap-Up

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Tom is joined by Natalie Derse, CFO of Gen. Natalie shares how she and her CEO delivered $330 million in cost synergies in under 18 months following Gen's merger with Avast, and what made that execution possible. She also breaks down her approach to AI-native finance, why the CFO is becoming the de facto Chief Trust Officer, and how real-time data from GE and eBay shaped her modern playbook. Natalie also shares her take on talent — what she looks for in every hire and how mentorship, not just work ethic, is what actually accelerates careers.

Guest quotes:
“ One of the biggest responsibilities I hold is to give the business as much clarity as I possibly can.  I don't know how you do that without a great hunger for more technology and data to help you guide.”

“We achieved $330 million of cost synergies in less than an 18-month period."

"You cannot be successful just running your own playbook and running your own game. You've got to connect and you've got to embrace, and really be humble enough to be coached."

Links & Resources:

Connect with Tom Gavaghan

Connect with Natalie Derse

Learn more about Kyriba

Learn more about Gen

YouTube Timestamps:

00:00 Show Intro and Guest Overview

00:36 Natalie's Background: GE, eBay, and Becoming CFO of Gen

01:15 Leadership Philosophy: Why She Refuses the Corner Office

02:43 Data-Driven Mindset Across Industries

04:11 CFO as Business Partner, Not Just Finance Leader

06:49 The Avast Merger: $330M in Synergies in Under 18 Months

08:49 Execution Strategy: Alignment, Clarity, and Relentless Commitment

10:44 Transparency as a Leadership Tool

11:18 Leveraging 500M Subscribers: Customer Data as a Leading Indicator

14:01 Cybersecurity Retention Rates Through Economic Cycles

16:23 MoneyLion and Financial Wellness: Two Sides of the Macro Spectrum

18:54 AI-Driven Fraud and the CFO as Chief Trust Officer

24:55 The Jellycorn Concept: AI and the Future of Headcount

28:49 Redesigning Finance Functions with AI

33:26 AI Adoption: Milestones, Not Light Switches

35:54 Building Human Talent: Curiosity and Engagement Over Credentials

40:30 Future Skills for Finance Leaders: Tech Fluency and Human Connection

35:54 Fasting, Family, and Staying Balanced as a CFO

37:04 Career Advice: Work Ethic + Mentorship = Acceleration

39:06 Wrap Up and Where to Follow Natalie and Gen

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Tom is joined by Marc Friend, CEO of Sift, a machine learning-powered fraud prevention platform that recently crossed $100M in revenue. Marc shares how he's restructuring the business to move from individual acts of heroism to true operational leverage — and what that requires at the organizational level. He breaks down how Sift thinks about fraud as a revenue enablement problem, not just a defensive one, and why agentic commerce is the next frontier no one has fully figured out yet. Marc reflects on how his background as an MIT systems engineer and 13-year VC shaped the way he architects companies and spots patterns worth replicating.

Guest quotes:
"You have to turn best practices into processes that are written down, so that when I say them and someone hears them, they're the same. Then you have to build a cadence around which you operate."

"When I come back to a merchant and say, I didn't authorize my agent to do that — that's a kind of fraud that we don't think about so much. Who's gonna take the risk of that is not decided."

"People are a lot more resilient than we give them credit for, and we are able to drive people much harder and further than they think they can go. People want to be challenged."

Links & Resources:

Connect with Tom Gavaghan

Connect with Marc Friend

Learn more about Kyriba

Learn more about Gen

YouTube Timestamps:

00:00 Show Intro and Guest Overview

00:25 Marc Friend Background: MIT to VC to CEO

01:51 Scaling Past $100M: Heroism vs. Systems

02:35 Re-Engineering the Org at Sift

03:25 Operational Leverage in SaaS

04:47 Competitive Landscape and Differentiation

05:46 Fraud as a Revenue Enabler

08:45 What Is Agentic Commerce?

09:23 Who Bears Risk When Agents Transact?

13:01 Sift's Data Advantage and ML Signals

13:45 Using AI as an Internal Challenger

16:37 Explainability and Feedback Loops in ML

21:15 Career Arc: Engineer to VC to CEO

23:10 Re-Architecting the Business at Each Growth Stage

25:14 Process, Documentation, and Cadence at Scale

26:25 Different Teams, Different Cadences

30:37 Leadership Lessons from the 1980 “Miracle on Ice”

33:04 Advice for Hiring or Becoming a CFO

34:00 CFO as Thought Partner and Business Architect

35:23 Wrap Up and Where to Find Sift

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Tom is joined by Trent York, CFO of Furnished Finder, a fast-growing marketplace connecting traveling professionals with furnished monthly rentals across the U.S. Trent explains how the company is capitalizing on the rapid growth of the midterm rental market. He also discusses the operating advantages of leading finance, HR, and legal under one organization, what he calls the “execution economy.”

Guest quotes:

“Mobility doesn’t stop just because the housing market freezes.”

“A CFO today needs to know a lot about a lot, not just finance.”

“If you can understand how every part of the business connects, you can move faster.”

Links & Resources:

Connect with Tom Gavaghan

Connect with Trent York

Learn more about Kyriba

Learn more about Furnished Finder

YouTube Timestamps:

00:00 Show Intro and Guest

01:07 Trent York Background

02:18 What Furnished Finder Does

02:44 Why Midterm Rentals Boom

04:13 Subscription Not Payments

05:22 Control and Simplicity

07:40 Housing Freeze and Renters

10:45 New Demand Segments

13:32 Modeling Mobility Trends

15:34 Marketplace Data Strategy

17:36 Proptech What Comes Next

19:51 International Expansion Plans

20:43 CFO Also HR and Legal

23:20 AI Pushback Framework

23:58 Trust but Verify Leadership

25:50 Upskill vs Hire Talent

28:59 Tech Stack Pitfalls

32:02 Career Growth Advice

34:25 Big vs Small Companies

36:04 Remote Travel Picks

37:27 Travel Rule and Family

38:47 Wrap Up and Book Picks

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Tom is joined by Jeanne Jones, CFO of Exelon, one of America’s largest energy delivery companies. Jeanne explains how Exelon creates long-term value in a highly regulated environment by focusing on operational excellence, disciplined capital allocation, and customer affordability. Jeanne also shares how she thinks about liquidity and balance sheet protection in a higher-for-longer interest rate environment, including why going long on debt and prioritizing certainty have helped Exelon weather volatility.

Guest Quote:

“We deliver consistent long-term value for our investors by doing the basics exceptionally well.”

“Affordability starts with controlling your own costs.”

“If you have size and scale but don’t manage it as a portfolio, you’re not optimizing that size and scale.”

Timestamps:
01:05 Exelon Investor Story

03:56 Regulated Revenue Engine

06:22 Data Centers and Fair Rates

10:56 Planning for Uncertain Load

12:30 Affordability in Practice

16:53 AI and Analytics Use Cases

19:37 Liquidity and Debt Strategy

23:58 Finance Tech That Matters

25:53 Portfolio Management Edge

26:54 Career Rotations at Exelon

30:20 Data Driven Leadership

32:03 Advice for Future Leaders

33:39 ERGs and Talent Pipelines

37:56 STEM Programs and Scholarships

40:03 Rapid Fire Questions

Links & Resources:

Connect with Tom Gavaghan

Connect with Jeanne Jones

Learn more about Kyriba

Learn more about Exelon

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