Shay CPA on the finance decisions that matter at each stage

Focus on early-stage tech companies

Shay CPA is a boutique accounting firm based in New York City. They specialize in helping early-stage tech companies with bookkeeping, financial reporting and tax compliance. They also support companies with R&D tax credits and fractional CFO work.

The sweet spot sits around Series A or B, but they pick up companies all the way from pre-seed. At that earliest stage, they focus on compliance fundamentals: filing 83b elections, Delaware annual franchise tax returns and setting up bookkeeping systems like QuickBooks. The less interesting stuff that becomes very expensive to fix later on.

The mistakes that cost founders 3-6 months of cleanup

When Shay CPA starts working with companies that waited too long to bring in accounting help, the same problems surface repeatedly.

Misclassifying employees as independent contractors instead of W2 employees. Co-mingling funds by running personal expenses like rent through the business. Letting tax deadlines and filing requirements pile up

"We often hear from founders who have had their companies for years, cycled through multiple accountants or just never found one that stuck," Akshay explains. "At that point it becomes a forensic accounting job to unravel everything."

For a new finance leader entering an organization where the books are a mess, that cleanup takes 3-6 months before they can start adding strategic value. That's 3-6 months where your most expensive hire is doing damage control instead of helping you make better decisions.

Repeat founders get their finances in order earlier

Repeat founders behave differently. They bring in accounting help before problems accumulate because they've lived through the pain of playing catch-up at Series A or B when they should be focused on growth.

"Repeat founders try to get their finance house in order way earlier," Akshay notes. "They've learned to trust outside vendors to help build that financial foundation from day one."

The tooling decisions that matter at each stage

Akshay breaks down the essential tools by revenue stage:

0 to $1M: Keep it simple. Basic bookkeeping software like QuickBooks Online. Spend management tools like Brex, Ramp, or Rho that double as a fintech bank. Startup-friendly payroll systems like Gusto, Rippling, or JustWorks.

$1M to $10M: This is where you need robust revenue recognition and need to move away from spreadsheets. Investors require GAAP-compliant financials. Tools like Sequence help track workflows like quote to cash properly. Investors now require GAAP-compliant financials. Lease accounting matters. The bar goes up across the board.

$10M to $100M: QuickBooks starts to creak. "QuickBooks is really good from zero to 10 million," Akshay says. "After that, once you have multi-entity consolidating different entities in different jurisdictions, it can be a bit of a challenge to scale." Two paths emerge here: layer on close automation software like Numeric to extend your existing stack, or rip and replace with a more robust ERP like a NetSuite.

The AI narrative is harming the accounting profession

"There's this line that keeps getting repeated: accountants won't be replaced by AI, but accountants that use AI will replace accountants. I think that's a misnomer given where AI actually is today."

The real-world impact hits the talent pipeline. Fewer students are studying accounting because they perceive AI will eliminate the profession entirely.

"If I'm 18 or 19 years old thinking about college and I keep seeing that AI is going to take over the entire accounting profession, I'm probably not going to study accounting. I'm going to go into finance, computer science, data analytics, maybe become an AI engineer instead."

His reality check is blunt: "We're a long way from completely replacing people in these workflows. AI agents today are a great tool, but that's where it stops. You still need someone in the loop to review, validate and ultimately take responsibility."

The accountability point lands hard. "If a bill gets paid incorrectly or your employees don't get paid, you can't call Sam Altman to fix that for you. OpenAI isn't taking responsibility. Your team is."

Advice for finance leaders considering fractional work

For finance or accounting leaders thinking about going fractional, Akshay has direct advice.

Treat it as a business from day one. "We've seen finance leaders take big haircuts just to establish a book of business. Founders will push for discounts or pro bono work. Don't fall into that trap."

Understand the bandwidth ceiling. Fractional CFOs can realistically juggle 4 or 5 engagements at once. Each one can feel like a part-time to full-time job. Many good fractional CFOs burn out and go back to full-time roles within 6-12 months.

Build a team if you want to scale. "If everything depends on your own expertise and time, it's really hard to build a business around that."

Know which discipline you're actually in. Finance and accounting get lumped together but they're different beasts. Accounting looks backward, recording transactions as they happen. Fractional CFO work looks forward: financial models, forecasts, strategic decisions. Tax is its own specialty entirely. Figure out where your skills actually fit.

The takeaway

The startups that scale cleanly invest in their financial foundation early. They choose tools that grow with them. They bring in expertise before problems compound into expensive cleanup projects.

And they recognize that despite the AI hype, someone will always be there to observe and take responsibility for these crucial workflows, like accounts receivable and general ledgers.