AMA on Scaling Finance: Lessons From 100+ CFOs on What Works (and What Doesn’t)

To scale finance effectively, CFOs must invest early in foundational systems, accept imperfect data, and balance control with growth. Insights from 100+ CFOs reveal what works—and what doesn’t—when building finance functions that can scale sustainably.

If you're a CFO or finance leader at a fast-growing startup, you've probably whispered it to yourself:

“My data is a mess.”

“I wish I'd implemented this system six months ago.”

Here’s the good news: you’re not alone.

In a recent CFO Connect webinar in partnership with Subscript, Phil from Subscript and Olivia, CFO of Promise, shared insights from conversations with over 100 finance leaders. What emerged was a candid discussion about the realities of scaling finance—the mistakes, the wins, and everything in between.

Whether you're a first-time CFO or a seasoned finance executive, this conversation offers practical wisdom you can apply immediately.

👇 Watch the full webinar recording below and read on to discover the key takeaways:

The Reality Check: What CFOs Are Really Dealing With

Q: What’s the biggest theme you’re hearing from CFOs right now?

Phil: Nine out of ten finance leaders think their data is an absolute hot mess. Everyone whispers it like they’re the only one facing this problem—but I hear it five times a day. Messy data is the norm, not the exception. The real question becomes: how do you operate when data will always be somewhat messy?

Beyond data chaos, there’s widespread scepticism about AI. I rarely hear, “AI is changing my life.” It’s more like, “This seems useful, but is it snake oil?” And the third big theme? Finance teams are doing a lot with very little. Small, mighty teams working hard to automate—few are “swimming in resources.”

Olivia: Absolutely. Finance teams are expected to contribute more while running leaner. With profitability back in focus, the pressure for real-time insight is intense.

How Finance Teams Evolve (and Where Things Get Messy)

Q: What patterns have you noticed in how finance teams evolve as companies grow?

Phil: There are three distinct stages:

1. Early stage: One or two generalists duct-taping systems together.

2. Growth stage: Data complexity explodes, sales deals break your systems, and hiring becomes chaotic.

3. Post-scale stage: Systems finally stabilise, and finance can focus on insights instead of firefighting.

Olivia: The key differentiator? The relationship between strategic finance and accounting. Your model is only as good as its inputs. Teams that automate foundational work expand their impact faster. At one SaaS company, accounting handled budgeting and forecasting because automation freed their time for strategy.

The Mistakes That Keep CFOs Up at Night

Q: What do CFOs underestimate about scaling finance?

Phil: Three things:

1. The cost of delay. Waiting too long makes things exponentially harder.

2. The emotional load. Saying no and making tough calls takes a toll.

3. Hiring. The wrong hire hurts; the right one transforms everything.

Olivia: Your first months as CFO are precious. Use that window to lay the foundations for the system. Skipping that step causes pain for years. The cost of delay is real—every month you wait, cleanup becomes much harder.

Control vs. Growth: The Balancing Act

Q: How do you balance control and growth without slowing everyone down?

Phil: Great CFOs are exceptional communicators. They articulate trade-offs early and get alignment. Clear documentation and socialisation across leadership are key.

Olivia: I wear two hats: protect the company and drive growth. That starts with mapping risks.

• For lending, it’s the treasury.

• For payments, it’s controls.

• For SaaS, it’s pricing discipline.

Once key risks are contained, you can confidently accelerate.

Systems and Automation: What Actually Works

Q: What’s actually working with tool stacks—and what isn’t?

Phil: There’s no magical tool. Problems start when you stack tools on shaky foundations. What works is clarity—knowing your goals, planning implementations, and setting expectations.

Olivia: Innovation in the CFO tech stack is exploding. Peer conversations help you cut through the noise and choose what best fits your business.

Making the Transition: From Legacy to Flexible Systems

Q: How do you move from legacy tools to modern systems?

Olivia: Draw your data flows before choosing a provider. Map integrations and plan your PMO resources to reduce invisible costs.

Phil: Experienced CFOs move fast because they’ve seen the cost of delay before. They know what they need and what it’s worth.

The AI Reality Check

Q: What AI tools or use cases are CFOs exploring?

Phil: Honestly, no “killer app” yet. Most CFOs use general AI tools like ChatGPT for spreadsheet analysis or policy drafting. But finance-specific AI still isn’t ready.

Olivia: AI shines in policy analysis, contract review, and month-end close for simpler orgs. But we’re still early—stay curious and keep experimenting. Be sceptical of AI hype—but stay informed. The payoff will come for those who keep learning.

The CEO–CFO Partnership

Q: Any lessons on CFO–CEO relationships during scaling?

Olivia: The foundation is trust and shared vision. The best CEOs want your perspective as CFO. Your job is to see around corners, challenge assumptions, and align on long-term goals.

First-Time CFO? Here’s What to Know

Q: What advice would you give to first-time CFOs?

Olivia: The clarity is refreshing—but don’t underestimate your voice. The CEO expects guidance, not just execution.

Phil: Don’t go it alone. Join communities, learn from peers, and stay curious.

Key Takeaways

• Invest early in systems—the cost of delay is real.

• Messy data is normal; focus on improving it over time.

• Communication is your superpower for balancing control and growth.

• Map risks early so you can move fast confidently.

• No tool will fix everything—clarity and planning are the secrets.

• Be sceptical of AI hype, but keep experimenting.

• Build a strong CEO–CFO partnership based on trust and visibility.

• Don’t go it alone—lean on your CFO community.

FAQ: Scaling Finance and CFO Lessons

1. What’s the biggest challenge CFOs face when scaling finance? Messy, inconsistent data. The key is learning to operate effectively while progressively cleaning and integrating systems.

2. When should startups invest in finance systems? Earlier than you think. Delaying foundational systems can double cleanup time and cost later.

3. How can CFOs balance control and growth? By mapping risk zones, setting guardrails, and communicating trade-offs proactively across leadership.

4. What’s the role of AI in finance today? AI supports workflows such as contract review and policy analysis, but no single tool has yet dominated.

5. What makes the best CFO–CEO partnerships work? Trust, shared vision, and open communication. The CFO should act as the CEO’s strategic co-pilot, not just a financial gatekeeper.

What’s Next?

Whether you’re scaling from your first finance hire or running a global team, every CFO faces similar challenges—the difference is how fast you learn from others.

🎥 Watch the full webinar for deeper dives into:

• Data quality trade-offs

• Hiring and org design

• Moving from legacy to flexible systems

• Practical AI use cases

• The CEO–CFO partnership