24 Years at Armanino: Building Scalable Finance Teams

Reliable Accounting Becomes Non-Negotiable Post-Series A

"I think so many people under invest in finance and accounting," Dean notes. "The reality is, clean numbers matter. As you fundraise, or prepare for transactions, people will scrutinize your numbers and they need to stand up."

Armanino typically enters the picture post-Series A, when companies need to formalize their finance operations. This is when founders realize their scrappy approach has limits.

"A lot of people think finance is the last thing they need to worry about. But the sooner you build a scalable finance team, the faster you can actually hit the numbers you dream of.

Under-investing in finance costs 2-4x more later

Dean has seen a consistent founder pattern: pride in running lean on finance -- until it becomes a liability.

“People wear under-investing in finance like a badge of honor. But when a transaction gets close, that badge becomes an albatross.”

Companies that invest early in finance spend 2-4x less on cleanup. Those that wait scramble at the end, throwing money at preventable problems.

Success requires people, process, and technology working together at scale

What separates successful companies from struggling ones? "It's about people, it's about process, and it's about technology. The organizations that align all three will win. Everyone else becomes a mad dash at the end."

For technology, Dean breaks it down by stage:

$1-10M companies need:

• FP&A tools (Mosaic, Causal, or Cube for financial planning and analysis)
• AP automation (Bill.com, Ramp, or Brex for expense management)
• Revenue recognition tools (Sequence for subscription billing and revenue rec)

$10-100M companies should add:

• AI-native finance tools (Numeric for month-end close automation, Trullion for lease accounting, or DataSnipper for audit automation)
• ERP systems (NetSuite or Sage Intacct for comprehensive financial management)
• Consolidation tools (Workday Adaptive Planning or OneStream for multi-entity reporting)
• Internal controls automation (FloQast for month-end close or MindBridge for transaction monitoring)

"There's a new generation of finance tools out there. They are AI native. They're building automation into everything they do."

Investors now demand ROI projections and AI integration plans

The standards for financial reporting have shifted dramatically. "Back in the day, it was 'just 'show us revenue growth'. Today, it's much more complicated than that."

Investors now expect you to answer: Can we bullet point these? "How will future dollars be invested? What’s the ROI on those investments? How is AI integrated into your operations?"

"If you can't tell that story, today, I can't guarantee your next round of funding."

Customer momentum defines winning finance tools

Dean looks for real traction, not just noise, when evaluating finance software. “True momentum is when customers say, ‘It’s already good now, and imagine where it’ll be in 2 or 3 years.’ That’s when you know an ecosystem is taking off.”

The old era of a few dominant players is over, he adds. “The landscape is shifting fast.”

AI reduces prep from 6 hours to 2 minutes

At Armanino, Microsoft Copilot and custom GPTs now handle client research. “What used to take six hours of prep is now done in two minutes, investor research, common touch points, key questions, recent company news.”

Dean expects 1-2 person finance teams to scale companies to $50-100M, but only for "AI power users" who know the best tools and have implemented them confidently into their business.

Finance professionals must become AI power users

For finance professionals concerned about AI disruption, Dean sees opportunity rather than threat.

“If you can dive into the new CFO tech, your value skyrockets. You’ll be closer to founders and VCs because you’ll be telling the story of AI and finance.”

After 24 years, his advice comes down to three actions:

1. Hire finance expertise by $5M ARR and 75 employees.

2. Implement FP&A and revenue recognition tools before $10M.

3. Maintain transaction-ready documentation from day one.

Companies that follow this playbook avoid 2–4x cleanup costs. Those that don’t face investor skepticism at the worst possible moment.