Automate First — Why Tools Come Before People
When revenue grows, most founders panic-hire. The books fall behind, invoices pile up, vendor payments get missed, so they toss another body at the problem. Then another. And another.
They built a finance team of 12 to do work that three people and the right tools could handle in half the time. Payroll balloons. Headcount soaks up cash. Turnover gets worse because the work is tedious.
I’ve watched $20M companies burn through seven figures annually on a finance function that still can’t close the books on time. Why? They automated nothing. Humans became the automation.
The Back Office Assembly Line is Dead
This mindset comes from an era when headcount equaled horsepower: more clerks, more reconciliations, more reports, more control.
Today, that model bleeds you dry. Good accountants are expensive, and bored accountants quit. Manual tasks are the biggest morale killer in your back office.
Modern CFOs understand this: Automate everything first. Hire second. Humans handle exceptions, decisions, and strategy, not data entry.
The New Playbook: Tools, Not Bodies
At $5M in revenue, you don’t need three AP clerks. You need an AP automation tool that:
Collects vendor invoices,
Flags duplicates,
Routes approvals,
Pushes payments,
Syncs back to the GL,
And logs every step for audit.
Same for AR: automate invoicing, reminders, collections nudges. Stop paying humans to chase checks.
Same for reconciliations: daily bank feeds, auto-matching, instant discrepancy flags. Nobody needs to download CSVs at midnight anymore.
Real-World Example
A client of mine was stuck at $12M in revenue, bleeding cash across the org but especially on a bloated finance team:
Three full-time AP clerks,
Two AR specialists,
A controller buried in reconciliations.
We implemented best-in-class AP and AR automation and reconciliation tools. We re-trained their team as generalists. The headcount dropped from seven to three in six months. The books closed five days after the end of the month, not three weeks later.
Those freed-up dollars were reinvested in sales and product development. Revenue hit $20M a year later. The finance cost per dollar dropped by half. That one automation push alone freed $200,000 in overhead, directly adding to EBITDA, and that money funded ad spend and revenue growth instead of administrative salaries.
RAID Rule #1: Let the Robots Work Overtime
This is RAID in practice:
Redundant: Tools never call in sick.
Agile: You can scale transactions without hiring.
Intelligence: Humans focus on analysis, not data entry.
Data-Driven: Automated feeds mean real-time numbers, not guesses.
I tell every CEO: If you want a $50M company with a five-person finance team, every repetitive task must be eaten by a tool. Not someday. Today.
Where to Start
Not sure where to start? Here’s the must-have shortlist for a RAID-ready finance stack:
✅ Cloud Accounting System: QuickBooks Online or Xero at first, then NetSuite or Sage Intacct as you outgrow simple ledgers.
✅ AP Automation: Tipalti, BILL, or Melio.
✅ AR Automation: Chaser, Tesorio, or YayPay.
✅ Bank Reconciliation & Cash Management: Float, CashAnalytics, or your ERP’s auto-match engine.
✅ Expense Management: Ramp, Brex, or Expensify.
✅ FP&A Tools: Jirav, Cube, or Mosaic to ditch spreadsheet-only forecasting.
Start small. Add modules as you grow. Most pay for themselves in the time and FTE costs they save.
(Pro tip: I have affiliate links for every one of these tools. Use them, your back office will thank you.)
Your Future-State Back Office
When tools come first, you buy time back for your team. They stop being paper-pushers. They become analysts, advisors, and decision partners. They surface insights before your board asks for them. They focus on future cash flow, not reconciling last month’s bank statement.
No more building a finance department that collapses under its weight. Build a system where machines handle the drudgery and humans drive growth.
Next Up: Post #3 — Build Redundant Finance: No More Single Points of Failure
The next RAID principle: design your team so knowledge lives in the system, not in any one person’s head. When you automate and cross-train, you never fear vacation season again.
Follow along if you’re tired of paying people to copy and paste. Or message me — I build RAID finance teams for companies that hate wasting money.
#CorporateFinance #FinanceAutomation #RAID #MainStreetIQ #DigitalTransformation #ProcessAutomation
Why Most Finance Teams Fail to Scale
RAID: A new way of thinking about finance departments.
Most finance teams buckle somewhere between $15 million and $50 million in annual revenue. They limp along, patching holes with half-baked spreadsheets, stressed staff, and duct-tape processes that collapse the moment someone takes a vacation.
The result? Missed forecasts, late closes, investors pacing in their offices, and a CEO lying awake at night, replaying board meeting promises that the numbers can’t support.
For the past twenty years, I’ve been the cleaner that business leaders, boards, and founders call when this reality hits the fan. Startups. Private equity portfolio companies. Family businesses with big dreams. Tech companies are burning cash. The same story repeats: the company outgrows its finance function, but nobody notices until the cracks are big enough to trip over.
Three Classic Mistakes
Every time, it boils down to three choices that looked harmless early on but turned lethal at scale:
1️⃣ Wrong Tools
Young companies think a junior bookkeeper and QuickBooks are enough. The problem arises when spreadsheets become a permanent part of the infrastructure. I once walked into a $25 million revenue company where the monthly cash forecast was stored in 8 different Excel files. No single version matched the bank. Nobody could explain where the cash from last month went.
2️⃣ Wrong People
Hiring happens reactively. A founder’s cousin steps in to become the controller. The AP clerk also serves as the office manager and occasionally the HR administrator. Cross-training rarely happens because everyone is too busy. Knowledge resides in a few heads, and when those individuals leave, so does the system.
3️⃣ Wrong Priorities
The product team gets funding. Sales teams expand. Marketing experiments with agency spend. Meanwhile, finance is told to “keep up” with whatever tools and people they have. By the time the CEO wants a forecast for raising a Series B round or securing a line of credit, the data is a Frankenstein's monster of guesswork.
The $5M Trap Nobody Talks About
When companies pass $5 million in annual revenue, it feels like they’ve “made it.” Leadership celebrates by hiring an in-house controller, thinking the hard part is done.
But the seeds of future pain get planted right there. Most businesses treat finance like a cost center instead of an investment in control. They maintain the same tools, personnel, and ad-hoc processes while revenue doubles, then triples.
The result: more transactions, more vendors, more payroll complexity, and a team unequipped to keep pace. So, they throw bodies at the problem. More accountants. More payroll clerks. More confusion.
I’ve walked into companies spending millions per year on finance headcount yet still closing the books fifteen days late and guessing at their cash runway.
The Cost of Getting It Wrong
A brittle finance team won’t just cause late closes and sloppy reports. It can kill deals. I’ve seen private equity firms walk away from great companies because they had little confidence in the back office.
Banks shy away from extending lines of credit when the CFO can’t produce reliable working capital metrics. Surprise tax liabilities often blindside CEOs because nobody flagged potential cash traps early enough.
In every one of these scenarios, the root cause wasn’t the complexity of the business; it was the lack of a modern framework.
What a Modern CFO Should Build Instead
A finance function built to scale looks different. It runs leaner, but smarter. It bets on technology first, people second. It stays flexible and redundant. It uses data to steer the ship, not to create pretty reports for slide decks.
Imagine running a $50 million company with five or fewer finance professionals, each one cross-trained, equipped with an automated tool stack that replaces the drudgery. AP runs itself. Cash forecasting updates daily. Reconciliations match to the penny without manual intervention.
Team members cover each other because they’re trained that way. Sick days and vacations don’t cause chaos. Everyone knows the moving parts because the knowledge is institutionalized, not tribal.
Like Paul’s Boutique, It Borrows, Repurposes, and Reimagines What Could Be
I call this approach RAID:
Redundant. Agile. Intelligent. Data-Driven.
Like Paul’s Boutique, it borrows, repurposes, and reimagines. It samples the best ideas from preexisting frameworks, concepts, and methodologies, then stitches them together into something entirely new and practical.
No corporate bloat. No 50-slide decks that nobody reads. No sprawling org chart filled with people managing the people who manage the reports.
Flip the Script: What Becomes Possible
Companies running on RAID don’t fear audits, investor due diligence, or market shifts. They close their books in days, not weeks. They see real-time cash runway on their phone. They forecast with probabilities, not hope.
When RAID fixes these cracks, clients have seen cash forecasting errors drop by 90% and days of cash on hand grow by 30%, which lenders love. Boards sleep better. Founders scale faster. Valuations hold up under scrutiny.
The finance department stops being the last to know what’s happening and becomes the function that shows the company how to win with better decisions.
What’s Next in This Series
This marks the beginning of a deeper dive into building a RAID-ready finance function. Over the next few posts, I’ll break down:
✅ Why you must automate before you hire
✅ How to hire generalists who can do more than close the books
✅ How to keep your team agile as revenue and complexity grow
✅ How to ditch the vanity metrics
✅ How to hand investors a back office they trust, and pay more for
Your finance department should run like a RAID array: self-healing, high-performing, and engineered to scale long before you need it.
Next up: Post #2 — Automate First: Why Tools Come Before People
If your business sits anywhere between $5M and $100M and you suspect your finance back office is one good vacation away from imploding, follow along. Book a call or message me. I build RAID finance teams for a living, and they don’t break.
#CorporateFinance #MainStreetIQ #RAID #FinanceTeam #FinanceLeadership #FinancialPlanning #FPandA