PYMNTS Intelligence surveyed middle-market finance executives for the August 2026 edition of The 2026 Certainty Project, produced with Fynapse, and found that 62% have struggled to manage or scale cash flow forecasting, while 37% name it as their single biggest finance or back-office challenge. (PYMNTS, September 2, 2026: https://www.pymnts.com/back-office/2026/cfos-forecast-better-when-finance-sees-more/)
The report is specific about why. The problem is not a missing model. It is latency. Transactions take days to become reconciled financial information, so finance teams fill the gap with assumptions, pull numbers from several systems, and rebuild a current view in a spreadsheet. Leadership then makes a real-time decision on a number that was already old when it arrived.
This is the fourth pillar in the Enterprise Value Playbook, and it inherits everything from the first three. A documented strategy, accountable leaders, and documented processes all produce data. Pillar 4 asks whether that data reaches the leadership table fast enough, and clean enough, to change a decision before the decision is already made. Revenue is an outcome. Enterprise value is the objective. You cannot manage the objective on a number you do not trust.
YOUR FORECAST IS FAN FICTION. YOUR CRM WROTE THE FIRST DRAFT.
62% of middle-market finance executives struggle with cash flow forecasting, according to PYMNTS Intelligence. The model is not the problem. The inputs are. Every unintegrated acquisition adds another CRM and another version of the numbers.
The fix is not a new platform. It is a unified Revenue Intelligence strategy. I wrote about it this month for Top Sales Magazine.
This week’s concept sits in Pillar 4, Finance + Capital: you maintain strong visibility into margins, cash flow, forecasts, and leading indicators.
Where You Stand
Ask your leadership team for today’s gross margin and current cash position. Not last month’s close. Today’s. How long does it take to get an answer, and does anyone in the room dispute the number when it arrives? If the honest answer is that everyone waits for the close, that is your actual score.
The Failure Pattern
Margin, cash flow, and forecast data live in spreadsheets nobody fully trusts, reconciled inconsistently across functions, and delivered too late to influence the decisions that would have mattered. The monthly close package lands three weeks after the month ends and tells leadership what already happened. Every real-time call gets made on stale or contested numbers.
Kotter’s Step 1, Create Urgency, applies here in its most literal financial form. Financial visibility gaps rarely get fixed until a cash crunch forces the issue. Build a leading-indicator dashboard, not just a lagging close package, and review it at the same cadence as the operational KPI rhythm from Pillar 1. Every number on it gets a single source of truth and a named owner accountable for its accuracy. The urgency has to be built before the crunch, by treating stale financial data as an active risk rather than an accounting inconvenience. That is what gets this work funded and prioritized ahead of the emergency instead of after it.
The Win Condition
Leadership can answer a real-time question about current margin or cash position without waiting for the next close cycle. Every leading indicator has a named owner accountable for its accuracy and timeliness.
FROM THE CHAIRMAN
“How old is the number you just gave me? If margin and cash visibility run three weeks behind reality, you are not managing the business. You are reading its history.”
MARKET INTELLIGENCE
Three signals from this week across Venture Capital, Private Equity, Family Offices, and Capital:
Apollo Global Management capped withdrawals from Apollo Debt Solutions BDC, its roughly $26 billion non-traded private credit fund, for the third straight quarter, after investors asked to redeem 14.7% of shares against a standard 5% quarterly limit, down from 16.8% the quarter before. (Bloomberg, via Investing.com, September 22, 2026: https://www.investing.com/news/stock-market-news/apollo-limits-redemptions-as-withdrawal-requests-hit-147–bloomberg-4911738) My read: Investors who asked for their money back this year will have received roughly 75% of it once third-quarter payments clear. The fund has returned 8.2% since its 2022 launch, so performance is not the story. Liquidity is. A return figure tells an investor how the asset has done. It does not tell them when they can get their cash out. That is the Pillar 4 distinction between a lagging number and a leading one, playing out across a $1.8 trillion asset class.
Priority Technology Holdings, a Nasdaq-listed payments and banking technology company, agreed to be taken private at $8.05 per share in cash, roughly $1.6 billion in enterprise value, by an investor group led by its own Chairman and CEO, Thomas Priore, with equity from funds advised by Searchlight Capital Partners. (Priority Technology Holdings press release, via Yahoo Finance, September 21, 2026: https://finance.yahoo.com/markets/stocks/articles/priority-technology-holdings-announces-1-140414549.html) My read: The price is a 38% premium to the September 18 close, and an independent special committee negotiated it more than 30% above the initial proposal. No committee moves a price that far without its own defensible view of what the business is worth. A board without current, trusted numbers has nothing to negotiate with.
Citi Wealth’s 2026 Global Family Office Report, drawn from 351 family offices across 41 countries surveyed in June and July, found that nearly half shifted capital toward public equities, now the top destination for new investment, while nearly 90% reported positive portfolio performance year to date. (Citi Wealth, via Yahoo Finance, September 22, 2026: https://finance.yahoo.com/markets/stocks/articles/citi-wealth-2026-global-family-123000844.html) My read: Offices are also deploying AI across investment analysis, reporting, and workflow automation, prioritizing productivity over alpha. Read those two findings together. The most patient capital in the market is moving toward the asset class that prices every day, and spending its technology budget on faster reporting for everything else. Any operating company raising from that capital should expect to be asked how old its numbers are.
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FROM THE TIP OF THE SPEAR
Sixty-two percent (62%) of middle-market finance executives say they struggle to manage or scale cash flow forecasting. PYMNTS published that number this month, and the instinct it produces almost every time is to buy a better forecasting tool.
A tool does not fix latency. If transactions take days to become reconciled numbers, a faster model simply produces a more confident guess on the same stale inputs. The problem is not the forecast. It is the age of the data feeding it, and the fact that three functions still argue about which version of it is right.
This week the market priced that problem three different ways. Apollo’s private credit investors learned that an 8.2% return does not tell you when you get your cash back. A special committee at Priority Technology negotiated a take-private price more than 30% above the opening offer, which no committee does without a defensible view of value. Family offices, the most patient capital there is, moved toward assets that price every day and put their technology budgets into faster reporting.
Pillar 4 starts here because every other financial decision depends on it. You cannot allocate capital intentionally, manage pricing and mix, or size a financing structure on numbers you do not trust. Ask yourself the Chairman’s question this week: How old is the number you just gave your board? If the answer is three weeks, you are not managing the business. You are reading its history.
COME TEACH THE CHAPTER THE TEXT BOOK SKIPPED.
My NYU graduate students study how companies scale, raise capital, and exit. The textbooks cover the theory. You lived the part they leave out.
If you have scaled a company, exited one, raised capital, or sat across the table when a deal was won or lost, give my students one session this fall/spring, LIVE in NYC (or virtual).
From the Tip of the Spear is my weekly publication for executives who are building something real. One issue, every Tuesday. A field report from active operator engagements, one principle with supporting data, and market intelligence from across my VC, PE, and family office network.
