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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:
“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:
“ 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:
“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:
"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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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.”
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
Connect with Tom Gavaghan
Connect with Jeanne Jones
Learn more about Kyriba
Learn more about Exelon
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In this episode, Tom is joined by Colin Wittmer, CFO of PwC. Colin's 31-year journey at PwC has seen him transition from the audit practice to a leadership role in finance, with a significant focus on deals and transaction services. Unlike the typical technology-centric CFO, Colin emphasizes the importance of human skills in AI-driven transformations. He offers insights into the evolving role of finance leaders, the impact of AI, and how to cultivate leadership within the organization.
Guest Quote:
“As a CFO, you see the whole picture… where a good CFO really excels is being able to connect the dots so everyone understands how something happening in one part of the business affects the rest.”
“If you start managing the business like you have a lot of cash, you can easily go sideways when things get tough. It’s maintaining that discipline in good times and in bad times.”
“Make the tough decisions early and stay the course. The companies that don’t come out of restructuring are the ones that defer making the hard decisions.”
Timestamps:
01:07 Colin Wittmer's Career Journey
02:27 Insights on M&A and Finance Leadership
07:34 The Role of AI in Modern Finance
08:49 AI Implementation at PwC
12:58 Balancing Human Skills and Technology
14:44 Continuous Learning and Adaptation
25:43 Advice for Aspiring CFOs
26:50 Balancing Client and Firm Management
27:54 The Importance of Leadership
28:26 Evaluating Career Decisions
29:54 Market Trends in M&A
31:52 Red Flags in Finance Functions
34:58 Future of the CFO Role
41:30 Personal Insights and Hobbies
44:41 Recommended Reads and Conclusion
Links & Resources:
Connect with Tom Gavaghan
Connect with Colin Wittmer
Learn more about Kyriba
Learn more about PwC
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In this episode, Tom is joined by David Smith, CFO at RevSpring, for a wide-ranging conversation on what a true 360-degree finance leader looks like. David shares how his rare path, from private equity investor to CEO to CFO, shapes the way he connects strategy, operations, and value creation across the entire business. He also explains why discipline, transparency, and partnership are essential in both turnarounds and high-growth environments, and how he helps teams stay engaged by empowering them to think and act like owners.
Guest Quote:
“As a CFO, you see the whole picture… where a good CFO really excels is being able to connect the dots so everyone understands how something happening in one part of the business affects the rest.”
“If you start managing the business like you have a lot of cash, you can easily go sideways when things get tough. It’s maintaining that discipline in good times and in bad times.”
“Make the tough decisions early and stay the course. The companies that don’t come out of restructuring are the ones that defer making the hard decisions.”
Timestamps:
00:50 David Smith's Unique CFO Perspective
04:48 Insights on Private Equity and Turnarounds
10:26 The Importance of Forecasting and Cash Flow Management
13:21 Balancing CFO Responsibilities and Team Motivation
20:52 Building Trust Through Small Wins
23:14 Leveraging AI in Finance
28:19 International Experience and Its Impact
33:35 Future of Finance Roles
Links & Resources:
Connect with Tom Gavaghan
Connect with David Smith
Learn more about Kyriba
Learn more about RevSpring
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