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83% of CEOs say AI depends on people. Only 25% use it regularly.

October 13, 2026 By Tip of the Spear

ISSUE XXVIII

FROM THE TIP OF THE SPEAR

SAM PALAZZOLO

IBM’s 2026 CEO Study surveyed 2,000 CEOs and equivalent senior leaders across 33 geographies. 83% say AI success depends more on people’s adoption than on technology. The same CEOs say only 25% of their workforce uses AI regularly as part of their job. (IBM Institute for Business Value, May 2026: https://newsroom.ibm.com/2026-05-04-ibm-study-ceos-are-reshaping-c-suite-roles-for-the-ai-era)

Read those two numbers together. CEOs know the constraint is people, not technology. Three in four of those people are not using it regularly. The capability gets bought, handed to IT or a data team, and launched. The rest of the organization is never authorized to act on what it produces. A model only IT can act on does not change how the company decides. It changes what the company spends.

This is the second Pillar 1 concept in the Enterprise Value Playbook, and the arc now returns to where it started. The first five concepts built the inputs: a documented strategy, accountable leaders, documented processes, trusted financial visibility, and a growth plan every function can explain. This concept asks whether the decisions made against all of it are getting faster and better. AI accelerates whatever decision-making pattern already exists. Applied to a disciplined process, it compounds good judgment. Applied to a fragmented one, it produces confident, fast, wrong answers.

YOUR 2027 BUDGET IS LAST YEAR​
​WITH A HAIRCUT.

Every October, management rolls forward last year’s run rate and negotiates percentages. That produces a budget. It rarely produces enterprise value.

This month I published a piece on why. A budget should not be a forecast of what the company will spend. It should be a decision about what the company is trying to become, and which investments will increase its value.

Read it here: https://tipofthespearventures.com/from-budget-to-enterprise-value-how-leaders-should-approach-budget-season/​

Before your plan goes to the board, I will run one Capital Allocation Review with your leadership team. You leave knowing where your capital is compounding and where it is habit. If we do not find at least one line you would fund differently, you have lost one hour.

I am holding a limited number for October. Reply “Capital Review” to reserve one.

THE PRINCIPLE

This week’s concept sits in Pillar 1, Strategy + AI: you use data and technology, including AI where relevant, to make faster and better decisions.

Where You Stand

Ask your leadership team to name one decision made last quarter that went differently, in direction or in speed, because of a data or AI capability you own. Then ask who outside IT is authorized to act on what that capability produces. If the room goes quiet on either question, that is your actual score.

The Failure Pattern

AI gets treated as a bolt-on tool assigned to IT rather than a capability embedded in how decisions actually get made. Leadership adopts a dashboard or a model, celebrates the launch, and six months later cannot point to a single decision that changed because of it. The tool exists. The decision-making pattern underneath it never did.

The Kotter Principle at Work

Kotter’s Step 5, Empower Broad-Based Action, is the relevant failure point here. Organizations frequently hand a powerful new capability to a narrow group, usually IT or a data science function, without removing the structural barriers that prevent the rest of the organization from acting on what it produces. A predictive model nobody outside of IT is authorized to act on is not a decision-making improvement. It is a report nobody reads. Identify the three highest-stakes, highest-frequency decisions in the business before selecting any tool. Map how those decisions get made today, who is involved, what data they use, how long it takes. Apply AI specifically to accelerate or improve that mapped process, not as a separate initiative competing for leadership’s attention. The tool serves the decision. The decision never serves the tool. Budget season is the natural moment to apply it: before another AI line item gets funded for 2027, name the decision it is meant to change and the people authorized to act on it.

The Win Condition

Leadership can name a specific decision that changed, in direction or in speed, because of a data or AI capability in the last quarter. The tool has a named owner accountable for adoption, not just for implementation.

FROM THE CHAIRMAN

“Tell me about a decision this quarter that would have gone differently without the data or AI capability you are describing. If you cannot name one, you have bought a tool, not changed how you decide anything.”

MARKET INTELLIGENCE

Three signals from this week across Venture Capital, Private Equity, Family Offices, and Capital:

  1. KKR / Gen II Fund Services. KKR agreed to acquire Gen II Fund Services from Hg and General Atlantic at a total enterprise value of $5.1 billion. Gen II administers funds for more than 275 private capital managers representing over $2 trillion in assets. Since Hg and General Atlantic invested in 2020, Gen II’s revenue and EBITDA have quadrupled, and Hg credits the team with driving AI and automation across client onboarding and bank reconciliations. KKR plans further investment in AI-enabled solutions and a broad-based employee ownership program. (General Atlantic press release, October 6, 2026: https://www.generalatlantic.com/media-article/kkr-to-acquire-gen-ii-fund-services-for-more-than-5-billion-from-hg-and-general-atlantic/) My read: Look at where the AI went. Not a strategy deck, not an innovation lab. Two named, high-frequency processes: onboarding a client and reconciling a bank account. That is the right order: pick the decision, then the tool. The employee ownership program matters as much. Kotter’s Step 5 is about removing the barriers that keep the broad organization from acting. Ownership gives every employee a reason to act on what the tools produce.
  2. Schneider Electric / PTC. Schneider Electric agreed to acquire PTC, the Boston maker of computer-aided design and product lifecycle software, in an all-cash deal valued at $22.6 billion. PTC shares closed up 33%. Schneider shares fell 10%. Both companies are adding AI features to make better use of the data their software collects, and analysts described the combination as a large industrial data-management platform. (The Boston Globe, October 5, 2026: https://www.bostonglobe.com/2026/10/05/business/schneider-electric-ptc/) My read: Schneider did not pay $22.6 billion for a model. Models are available to everyone. It paid for the engineering and operating data that tells a model what is true inside a specific product and a specific plant. A model without that context produces confident, fast, wrong answers. The 10% markdown is the board-level question in public: will the combined company change how its customers decide, or will it sell them more software?
  3. Wittington Investments / Boots. Wittington Investments, the Weston family holding company behind Loblaw and George Weston Ltd., agreed to buy UK pharmacy chain Boots from Sycamore Partners for US$8.9 billion (about C$12.7 billion), including debt. Fairfax Financial will contribute up to US$2.3 billion and hold 50% after closing. Wittington keeps operational control, and Galen Weston becomes chairman. One analyst expects the two businesses to share best practices, and possibly infrastructure, with Shoppers Drug Mart. (The Canadian Press, via BNN Bloomberg, October 7, 2026: https://www.bnnbloomberg.ca/business/company-news/2026/10/07/family-behind-canadas-biggest-grocery-chains-buys-uk-drugstore-boots/) My read: The Westons have owned a national pharmacy chain in Canada since 2014. They are not buying Boots to learn how pharmacy decisions get made. They already know which decisions matter. Family capital split the economics and kept the decision rights in one place. That is the sequence this concept demands: know the decision first, then bring the capital and the tools to it.

SAM SPEAKS

Later this month I deliver “The Unrealistic Leader: Achieve Real Results by Being Unrealistic” to members of the Association of Revenue Cycle Professionals (ARCP). I speak to executive audiences on three core topics:

  • Scaling and Exiting the Business for Maximum Value. The leaders who capture maximum value at the table treat the exit as a strategy, not an event.
  • The Unrealistic Leader. The most dangerous thing a leader can do is become reasonable too early.
  • The Price Pressure Playbook. Buyers have a playbook. This talk gives sellers the 20 moves that counter it.

If your professional association or an upcoming conference is building its agenda to close out 2026 or plan 2027, let us connect: speaking@tipofthespearventures.com

FROM THE TIP OF THE SPEAR

Eighty-three percent (83%) of CEOs say AI success depends more on people’s adoption than on technology. The same CEOs say twenty-five percent (25%) of their workforce uses AI regularly. That gap is the failure pattern in two numbers.

A tool is not a decision capability. It becomes one when someone names the decision it serves, maps how that decision gets made today, and authorizes the people closest to the work to act on what the tool produces. Until then, AI sits with IT, produces reports, and changes nothing but the budget line.

This week the market showed what the alternative looks like. KKR paid $5.1 billion for a fund administrator that pointed AI at two specific processes, onboarding and reconciliation, and plans to put ownership in its employees’ hands. Schneider Electric paid $22.6 billion for the engineering data that gives industrial AI something true to work from. The Weston family bought Boots with a pharmacy operating playbook already in hand, and kept the decision rights in one place.

Budget season is where this gets decided. Every 2027 plan has an AI line in it. Ask the Chairman’s question this week: Tell me about a decision this quarter that would have gone differently without the data or AI capability you are describing. If you cannot name one, you have bought a tool, not changed how you decide anything.

100% GUARANTEED.

Executive Performance Coaching for CEOs and senior leaders who are scaling something real. We define the results in writing before we start. If you are not satisfied with them, you do not pay.

DO NOT PAY ME UNLESS YOU GET RESULTS.

Reply “Coaching” or reach me directly: sp@tipofthespearventures.com

UNTIL NEXT TUESDAY

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.

Sam Palazzolo, Tip of the Spear Ventures sp@tipofthespearventures.com +1 702.970.8847

Operator. Investor. Educator. Enterprise Value Strategist.​
Scaling organizations. Maximizing enterprise value.

Built with Kit​

Filed Under: Blog

Your growth plan is not a Finance exercise

October 6, 2026 By Tip of the Spear

ISSUE XXVII

FROM THE TIP OF THE SPEAR

SAM PALAZZOLO

​Chief Executive‘s August 2026 CEO Confidence Index asked 285 CEOs where they will focus for the rest of the year. Revenue and market-share growth topped the list at 55%. Only 13% named talent and organizational capabilities among their top two priorities. (Chief Executive, August 2026: https://chiefexecutive.net/in-final-stretch-of-the-year-ceos-push-for-growth-lean-into-ai/)

Read those two numbers together. More than half of CEOs are committing to growth. Almost none are committing to the capacity that delivers it. The number gets set in the boardroom, handed to sales, and never translated into what finance, operations, talent, and product need to do differently. Growth that sales generates and operations cannot deliver is not growth. It is churn with a delay.

This is the first Pillar 5 concept in the Enterprise Value Playbook, and it inherits everything from the first four. A documented strategy, accountable leaders, documented processes, and trusted financial visibility are the inputs. Pillar 5 asks whether the growth plan connects them, or whether it is a sales target with a company name attached. Revenue is an outcome. Enterprise value is the objective. A plan only one function can explain moves neither.

YOUR 2027 BUDGET IS LAST YEAR​
​WITH A HAIRCUT.

Every October, management rolls forward last year’s run rate and negotiates percentages. That produces a budget. It rarely produces enterprise value.

This month I published a piece on why. A budget should not be a forecast of what the company will spend. It should be a decision about what the company is trying to become, and which investments will increase its value.

Read it here: https://tipofthespearventures.com/from-budget-to-enterprise-value-how-leaders-should-approach-budget-season/​

Before your plan goes to the board, I will run one Capital Allocation Review with your leadership team. You leave knowing where your capital is compounding and where it is habit. If we do not find at least one line you would fund differently, you have lost one hour.

I am holding a limited number for October. Reply “Capital Review” to reserve one.

THE PRINCIPLE

This week’s concept sits in Pillar 5, Accelerated Growth: you have a clear multi-year growth plan with aligned targets, metrics, and ownership across departments.

Where You Stand

Ask your CFO, your head of operations, and your head of talent to state their specific, measurable contribution to next year’s growth target. Not the sales number. Theirs. If any of them has to ask sales what the plan requires of them, that is your actual score.

The Failure Pattern

The growth plan exists as a single top-line revenue number, owned by sales alone, with no operational, financial, or talent plan built to support it. The number gets set in the boardroom, sales gets the quota, and it never gets translated into what every other function needs to do differently to make it real.

The Kotter Principle at Work

Kotter’s Step 3, Form a Strategic Vision, is the direct application. A growth target is not a vision. A vision explains how every function’s specific contribution connects to the larger outcome. Without that translation, each department is left to guess at its own role in a plan it never actually helped build. Translate the multi-year target into owned sub-targets for every function: finance’s capital and margin plan, operations’ capacity plan, talent’s hiring and development plan, product’s roadmap. Tie all of them to the same top-line number and review them together, not in departmental isolation. Budget season is the natural moment to do it, because it is the moment every function is already asking for capital.

The Win Condition

Every function leader can state their specific, measurable contribution to the multi-year growth target without needing to ask sales what the plan actually requires of them.

FROM THE CHAIRMAN

“This growth number is on the strategic plan. What does finance need to do differently because of it? What does operations need to do differently? If only sales can answer that question, this is not an enterprise growth plan. It is a sales target with a company logo on it.”

MARKET INTELLIGENCE

Three signals from this week across Venture Capital, Private Equity, Family Offices, and Capital:

  1. Blackstone combined two defense engineering firms, Applied Systems Engineering and Technology Service Corp., into a new platform called Falcata, backed by more than $1 billion in debt and equity. Falcata builds navigation and guidance systems for interceptors that defend against missiles and drones, and Blackstone expects to add more companies to it. President Jon Gray said the firm has put $20 billion into defense and aerospace over five years and expects the pace to increase. (Bloomberg, via Advisor Perspectives, October 1, 2026: https://www.advisorperspectives.com/articles/2026/10/01/blackstone-bets-1-billion-firm-aimed-boosting-us-defense) My read: Blackstone did not buy two companies and look for a thesis afterward. It named a choke point in the defense industrial base, the guidance “brains” of an interceptor, and assembled a platform to attack it, with the next acquisitions already in the plan. Every add-on arrives with a defined role. That is a multi-year growth plan with the capacity built ahead of the revenue.
  2. Thomson Reuters closed the sale of a 51% stake in its Global Print business to KKR-advised capital accounts, roughly $500 million in gross proceeds, and kept the other 49%. The business now operates independently as Westbridge Print, serving legal and tax professionals in 13 countries. Thomson Reuters said the transaction sharpens its focus on AI solutions for the legal, tax, audit, and compliance industries. (Thomson Reuters press release, October 1, 2026: https://investors.thomsonreuters.com/news-releases/news-release-details/thomson-reuters-and-kkr-complete-joint-venture-global-print) My read: A multi-year growth plan also decides what does not belong in it. Print has a long history and loyal customers, and no role in a plan built around AI. Thomson Reuters did not starve it inside the portfolio. It gave the business an owner with a plan of its own and kept 49% of the upside. A unit with no role in the growth plan is not neutral. It consumes management attention the plan needs.
  3. Family offices made 42 direct investments in September, down from 52 in August, according to Fintrx data reported by CNBC, while writing into some of the largest rounds of the month: Duquesne Family Office in Fab2’s $500 million raise and Precision Neuroscience’s $250 million round, and John Doerr’s family office co-leading Mazama Energy’s $135 million Series B. (CNBC, October 1, 2026: https://www.cnbc.com/2026/10/01/billionaire-family-offices-back-geothermal-energy-in-september.html) My read: Fewer swings, bigger checks, and a stated preference for teams showing real-world progress. The most patient capital in the market is paying for evidence that the plan is already working, not for the plan. A founder raising from that capital should expect to be asked what the growth target requires of operations, talent, and capital, and whether that work has started.

SAM SPEAKS

Later this month I deliver “The Unrealistic Leader: Achieve Real Results by Being Unrealistic” to members of the Association of Revenue Cycle Professionals (ARCP). I speak to executive audiences on three core topics:

  • Scaling and Exiting the Business for Maximum Value. The leaders who capture maximum value at the table treat the exit as a strategy, not an event.
  • The Unrealistic Leader. The most dangerous thing a leader can do is become reasonable too early.
  • The Price Pressure Playbook. Buyers have a playbook. This talk gives sellers the 20 moves that counter it.

If your professional association or an upcoming conference is building its agenda to close out 2026 or plan 2027, let us connect: speaking@tipofthespearventures.com

FROM THE TIP OF THE SPEAR

Fifty-five percent (55%) of CEOs rank growth among their top priorities for the rest of the year. Thirteen percent (13%) rank talent and organizational capability there. That gap is the failure pattern in two numbers.

A growth target is not a plan. It is a number. It becomes a plan when finance knows the capital and margin it requires, operations knows the capacity, talent knows the hires and the development, and product knows the roadmap. Until then, sales carries the entire target and every other function guesses at its role.

This week the market showed what the alternative looks like. Blackstone named a choke point in the defense industrial base and built Falcata around it, with the next acquisitions already in the plan. Thomson Reuters decided its print business had no role in an AI-led growth plan and handed it to an owner that would build one. Family offices did fewer deals and wrote bigger checks to teams showing real-world progress.

Budget season is where this gets decided. The 2027 plan either translates the growth number into every function’s budget, or it rolls forward last year’s run rate and hands the number to sales again. Ask the Chairman’s question this week: What does finance need to do differently because of this growth number? If only sales can answer, you do not have an enterprise growth plan. You have a sales target with a company logo on it.

100% GUARANTEED.

Executive Performance Coaching for CEOs and senior leaders who are scaling something real. We define the results in writing before we start. If you are not satisfied with them, you do not pay.

DO NOT PAY ME UNLESS YOU GET RESULTS.

Reply “Coaching” or reach me directly: sp@tipofthespearventures.com

UNTIL NEXT TUESDAY

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.

Sam Palazzolo, Tip of the Spear Ventures sp@tipofthespearventures.com +1 702.970.8847

Operator. Investor. Educator. Enterprise Value Strategist.​
Scaling organizations. Maximizing enterprise value.

Built with Kit​

Filed Under: Blog

From Budget to Enterprise Value: How Leaders Should Approach Budget Season

October 1, 2026 By Tip of the Spear

Every October, the same pattern repeats inside companies. The sponsor has underwritten a value creation plan. The board expects measurable progress against it. Management opens a spreadsheet, rolls forward last year’s run rate, and spends six weeks negotiating percentages.

Rolling forward last year’s run rate produces a budget. It rarely produces enterprise value.

The question that matters is not “How much can we spend next year?” It is “Where does the next dollar of capital create the most enterprise value between now and exit?”

I have sat on every side of that table. More than 12 years ago I led a SaaS company to a PE exit. Since then I have scaled 15 organizations from $5M to $500M, two of them past $1B, working alongside leadership teams, serving on boards, and teaching the same discipline at NYU. The budgets that moved valuation shared four disciplines: Value, Zero-Based Thinking, Strategic Guardrails, and Dynamic Allocation.

Sam Palazzolo From Budget to Enterprise Value

1. Fund Outcomes, Not Departments

The weakest budget question is “What do you need next year?” The right question is “What outcome are we buying?”

Every material budget line belongs in one of three categories, and each maps directly to a lever in the value creation bridge.

RUN THE BUSINESS. The margin lever. The baseline cost of operating the company. The mandate is productivity, automation, and capacity utilization. This baseline should shrink as a percentage of revenue every year. When it does not, it compounds silently and erodes EBITDA.

GROW THE BUSINESS. The revenue lever. Investments that directly increase revenue, customers, share, or commercial capacity: sales capacity, proven channels, expansion revenue, new geographies. The standard is measurable acceleration within the plan year.

TRANSFORM THE BUSINESS. The multiple lever. Investments that change the company’s economics or competitive position: AI, new business models, new markets, platform technology. The mandate is disciplined optionality. These are the investments a buyer pays a higher multiple for, and the ones most often starved in a cost-driven budget.

The board should see the mix across all three explicitly. A company that places nearly all of its capital in Run is managing for stability. A company with no capital in Transform is selling the next owner a business that has already peaked.

This classification moves the conversation from “What can we cut?” to “What are we funding, why, and what will it produce?”

2. Apply Zero-Based Thinking Without Zero-Based Bureaucracy

Full zero-based budgeting is rarely the right tool for a scaling company. Executed poorly, it consumes management capacity the business cannot spare and returns little strategic value.

Apply zero-based thinking instead, targeted at the four categories that accumulate fastest: headcount, software, contractors, and discretionary programs. Nothing carries forward by default.

Every significant request answers five questions:

  • What business outcome does this investment enable?
  • What capacity constraint does it remove?
  • What is the expected return, and over what period?
  • What happens if we do not fund it?
  • What evidence would cause us to increase or decrease it?

Technology spend deserves particular scrutiny. Companies add applications faster than they retire them. The cost is not only the license line. It is fragmented capability, duplicated functionality, and management complexity that a buyer will find in diligence.

The objective is not indiscriminate cutting. It is to ensure every material dollar has a reason to exist.

3. Set Strategic Guardrails Before Anyone Opens the Spreadsheet

Strategy sets the budget. The budget does not set strategy.

Before Finance consolidates a single departmental request, the executive team and the board agree on three to five non-negotiable priorities for the year, each tied directly to the investment thesis. Each priority carries an explicit budget implication.

Priority: Grow enterprise ARR 30%. Implication: Incremental sales and marketing investment must show a direct line to enterprise growth. Requests serving lower-priority segments are deprioritized.

Priority: Expand operating margin to 15% ahead of an exit process. Implication: New headcount requires evidence that existing capacity is fully utilized or that the role produces a measurable economic return.

Priority: Deploy AI-enabled productivity across the enterprise. Implication: Every technology request names the process being improved, the productivity gain, and the metric that will prove it.

Guardrails convert budget season from a series of departmental negotiations into a single decision system the board can govern.

4. Replace the Static Budget With Dynamic Allocation

A 12-month budget assumes management can predict what the business will need a year from now. Scaling companies rarely can.

Build three scenarios:

BASE CASE. Current assumptions hold.

UPSIDE CASE. Commercial performance exceeds plan. What additional investment becomes attractive, and how fast can it deploy?

DOWNSIDE CASE. Revenue, margin, funding, or market conditions deteriorate. What gets cut first, and what protects covenants, runway, and the core of the value creation plan?

Then tie spending to triggers. A $500,000 Q3 marketing expansion is not released because it appears in the annual plan. It is released when the business hits defined revenue, pipeline, or customer milestones.

The principle: commit capital progressively as evidence improves.

This gives the board two things a static budget cannot: financial discipline and strategic agility. It also creates the bridge to a rolling four-quarter forecast, refreshed as actual performance moves, so the budget becomes a management instrument rather than an annual artifact.

The Execution Roadmap

A framework matters only if it changes how budget season runs. The work fits a six-week management cycle.

Weeks 1 and 2: Diagnose

Run a Cost and Capacity Audit. Identify underutilized software, redundant capabilities, organizational bottlenecks, low-return programs, and initiatives that have grown in scope without a corresponding business outcome.

This establishes the baseline before anyone starts defending next year’s number.

Week 3: Align

Convene the executive team for a Strategic Alignment Session. Lock the three to five priorities, financial targets, investment guardrails, and scenario assumptions that will govern the budget.

The framework is constant. The metrics change with the capital structure.

  • PE-backed: EBITDA growth, cash conversion, leverage, and exit readiness.
  • Venture-backed: growth efficiency, burn multiple, runway, ARR, net retention, and the next raise.
  • Family office and privately held: growth, liquidity, distributions, succession, and long-horizon strategic investment.

Weeks 4 and 5: Challenge

This is where the CEO, the CFO, or an independent board member acts as the friendly challenger. Every leader’s request is stress-tested with two questions:

“If we cut this line by 20%, what specific outcome breaks?”

“If we increase this investment by 20%, what measurable outcome improves?”

The first exposes embedded cost. The second exposes whether an investment has real growth potential. Together they separate habitual spending from strategic spending.

Week 6: Allocate and Approve

The deliverable is not a consolidated budget. It is a capital allocation plan tied to business outcomes and KPIs.

The CEO, the board, and the investors should see on one page where capital is deployed, why, what outcome it is expected to produce, and which conditions trigger a change of course.

At that point, budget approval becomes a leadership decision rather than a Finance exercise.

The Bottom Line

This budget season is the moment to decide what the organization will protect, accelerate, transform, and stop funding.

The framework is deliberately simple. Shift from cost to value. Apply zero-based thinking. Set strategic guardrails. Build dynamic allocation. Execute through six weeks of diagnosis, alignment, challenge, and allocation.

Sponsors underwrite the thesis. The budget is where management proves it can execute it.

The question for every CEO, board, and investor is not whether the company can afford the budget. It is whether the company is allocating scarce capital against the few priorities that will move enterprise value.

That is what budget season should be about.

Sam Palazzolo is an Enterprise Value Strategist who works with CEOs, boards, and investors on scaling organizations and maximizing enterprise value. He is Managing Director of Tip of the Spear Ventures and a Professor of Management and Entrepreneurship at NYU’s School of Professional Studies.

Sam Palazzolo From Budget to Enterprise Value

Filed Under: Blog Tagged With: sam palazzolo, strategic budgeting for scaling companies, tip of the spear ventures

How Old Is the Number You Just Gave Your Board?

September 29, 2026 By Tip of the Spear

ISSUE XXVI

FROM THE TIP OF THE SPEAR

SAM PALAZZOLO

​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.

Read it here: https://topsalesmagazine.com/issue/2026/Sep26_01/#page=21​

THE PRINCIPLE

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.

The Kotter Principle at Work

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:

  1. 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.
  2. 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.
  3. 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.

WHY ONLY 100 PEOPLE WILL EVER GET THIS

Thirteen Executive Briefing Frameworks, monthly, board-ready. Plus a monthly Insider group Q&A. Founding Member seats: capped at 100, $1,200 for lifetime access. Reply “Briefings” for early access.

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).

Reach me @NYU: swp6951@nyu.edu​

UNTIL NEXT TUESDAY

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.

Sam Palazzolo, Tip of the Spear Ventures sp@tipofthespearventures.com +1 702.970.8847

Operator. Investor. Educator. Enterprise Value Strategist.​
Scaling organizations. Maximizing enterprise value.

Built with Kit​

Filed Under: Blog

Your Core Process Is One Resignation Away From Breaking

September 22, 2026 By Tip of the Spear

ISSUE XXV

FROM THE TIP OF THE SPEAR

SAM PALAZZOLO

​McKinsey surveyed organizational leaders for its 2026 State of Organizations report and found that two-thirds, 67%, believe their own organization is overly complex and inefficient, while the traditional fixes, restructuring, cost cuts, flatter hierarchies, are producing diminishing returns. (McKinsey & Company, February 19, 2026)

Read that number as a diagnosis of what actually sits underneath complexity. Restructuring the org chart does not fix a process that only one person knows how to run correctly. Cutting a layer of management does not make a workaround documented. Most leaders are treating a symptom because the underlying disease, undocumented process masquerading as institutional knowledge, stays invisible until the one person who understands it is gone.

This is the third pillar in the Enterprise Value Playbook, and it inherits everything from the first two. A documented strategy with individually accountable leaders still breaks down if the processes those leaders are accountable for exist only as tribal knowledge. Strategy tells the organization where to go. Accountability assigns who is responsible for getting there. Process is what makes the trip repeatable without that one person in the room.

YOUR CRM IS NOT THE PROBLEM.
YOUR BUSINESS WAS NEVER INTEGRATED.

Just 14% of organizations report significant success across a completed acquisition, according to PwC’s M&A Integration Survey. The gap is rarely the technology. It is Revenue Intelligence, the collective commercial knowledge a CRM should produce and too often does not, that determines whether leadership can trust the numbers behind growth strategy, capital allocation, and enterprise value.

I wrote about it this month for Top Sales Magazine: why CEOs, boards, and sales leaders need to stop asking which CRM platform to buy and start asking whether they have built a unified Revenue Intelligence strategy.

Read it here: https://topsalesmagazine.com/issue/2026/Sep26_01/#page=21​

THE PRINCIPLE

This week’s concept sits in Pillar 3, Operations + Technology: your core processes are documented, scalable, and executed consistently across the organization.

Where You Stand

Pick your single most important recurring process, the one that touches revenue, delivery, or the customer directly. Could a new hire execute it correctly from a written document alone, with no one walking them through it verbally? If the honest answer requires naming a specific person, that is your actual score.

The Failure Pattern

Core processes exist as tribal knowledge, executed slightly differently by every team that touches them, with no documented standard to train against or audit against. The process breaks the moment the one person who understood it leaves, gets promoted, or takes a vacation at the wrong time.

The Kotter Principle at Work

Kotter’s Step 1, Create Urgency, is the honest starting point here. Most organizations only document a process after it has already broken in a costly, visible way. Document every core process that touches revenue, delivery, or customer experience, not as a compliance exercise but as an operational asset. Standardize execution against that documented version and treat any deviation as a signal worth investigating, not a personal style choice. Building urgency before the breakage, treating undocumented process as an active risk rather than a someday project, is what actually gets the documentation done.

The Win Condition

Any core process can be handed to a new hire as a documented standard, without requiring a tenured employee to walk them through it verbally. Execution is consistent across teams, not dependent on which team happens to be doing it.

FROM THE CHAIRMAN

“What happens to this business the week your best operations person takes an unplanned two-week leave? If the honest answer is we would struggle, you do not have a process. You have a person, and people leave.”

MARKET INTELLIGENCE

Three signals from this week across Venture Capital, Private Equity, Family Offices, and Capital:

  1. Crusoe raised $3.9 billion in Series F funding at a $30.9 billion valuation, led by Atreides Management, Mubadala Capital, and Valor Equity Partners, to expand its AI data center buildout. (TechCrunch, September 17, 2026: https://techcrunch.com/2026/09/17/crusoe-raises-3-9b-to-build-massive-data-centers-and-small-modular-ai-factories/) The detail that matters is not the valuation. It is how Crusoe intends to deploy the capital: manufacturing modular data centers, called Spark, at its own facilities so it can install compute capacity quickly without staffing up a large construction workforce at every new site. That is Pillar 3 at industrial scale. The company turned building a data center into a documented, repeatable, manufactured process instead of a headcount problem.
  2. KKR emerged as the preferred bidder for Logoplaste, a Portuguese packaging manufacturer, in a deal that could value the company at more than 1.7 billion euros, after Ontario Teachers’ Pension Plan Board, which holds 60% of the company, moved to sell its stake. (Bloomberg, via Investing.com, September 16, 2026: https://au.investing.com/news/stock-market-news/kkr-emerges-as-preferred-bidder-for-portugals-logoplaste–bloomberg-93CH-4645082) A packaging manufacturer commands that price because its production lines run the same way regardless of which plant or which shift is running them. Consistency across a manufacturing footprint is not a nice to have here. It is the asset being priced.
  3. Family offices, managing an estimated $5.5 trillion in assets, are increasingly bypassing traditional venture funds to make direct investments and buy secondary stakes in AI companies, chasing deals that promise faster returns than a standard fund commitment. (TechCrunch, September 18, 2026: https://techcrunch.com/2026/09/18/family-offices-are-clamoring-for-ai-investments/) One family office advisor put the logic bluntly: offered a choice between a fund that triples an investment in three years and a deal that could do it in three months, the choice is easy. That speed comes at the cost of the process discipline a fund’s own diligence machinery normally provides. Pillar 3 does not disappear because the check gets written faster. It just moves the exposure from the fund manager’s desk to the family office’s, without the documented process to catch it.

ONLY 100 PEOPLE WILL EVER GET THIS

Starting this month, I am building a second home for this work on Substack, with a new Enterprise Value Playbook focus and a paid tier alongside the free issues you already receive.

The paid tier is called From the Tip of the Spear: Executive Briefings. Every month I release one Executive Briefing Framework, thirteen in total, each a board-ready deck answering the only question my work is built around: how you scale the organization and maximize enterprise value. Membership also includes a monthly Insider group briefing with live Q&A.

Founding Member seats are capped at 100, priced once at $1,200 for lifetime access. Annual access is $400. Seats will not reopen once the cap is reached.

Reply “Briefings” for early access before the general list opens, and I will send you the first one free. The free weekly edition continues without interruption either way.

FROM THE TIP OF THE SPEAR

Two out of three (67%) leaders think their own organization is too complex to run well. McKinsey published that number this year, and the instinct it produces almost every time is to redesign the org chart. Fewer layers. Cleaner reporting lines. A new structure that looks better in a slide than the old one did.

None of that touches the actual problem. A process that lives in one person’s head is not simplified by moving a box on an org chart. It is still undocumented. It still breaks the same way, the day that person is out sick, promoted, or gone.

Crusoe raised close to four billion dollars this week building a company on the opposite premise: manufacture the process, do not staff it. KKR is paying more than 1.7 billion euros for a packaging company priced on the fact that its production runs the same way no matter which plant is running it. Family offices are moving capital faster than the diligence process that used to slow them down, and every advisor quoted admits they know exactly what they are giving up to do it.

Pillar 3 is not a technology upgrade and it is not a reorganization. It is the discipline of writing down what your best people already know how to do, so the business does not depend on them remembering to show up. Ask yourself the Chairman’s question this week. If your best operations person took two weeks off tomorrow, would the business struggle? If the honest answer is yes, you do not have a process. You have a person, and people leave.

I WANT YOUR SCAR TISSUE IN MY NYU CLASSROOM

The discipline behind this newsletter is the same discipline I teach at NYU, across two courses: Scaling and Exiting the Business for Maximum Value, and Funding and Legal Approaches for Start-Ups. Each semester I bring operators into the classroom, live in NYC or virtual, to sit with graduate students working through the same problem from the practitioner side.

If you have scaled a company, exited one, raised capital, negotiated the legal terms of a deal, or sat across the table at the moment it was won or lost, I want to hear from you.

Reach me @NYU: swp6951@nyu.edu​

UNTIL NEXT TUESDAY

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.

Sam Palazzolo, Tip of the Spear Ventures sp@tipofthespearventures.com +1 702.970.8847

Operator. Investor. Educator. Enterprise Value Strategist.​
Scaling organizations. Maximizing enterprise value.

Built with Kit​

Filed Under: Blog

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