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Blog

Sales promised it. Operations never agreed to it.

October 20, 2026 By Tip of the Spear

ISSUE XXIX

FROM THE TIP OF THE SPEAR

SAM PALAZZOLO

Grant Thornton’s 2026 AI Impact Survey asked 950 senior executives across 10 industries whether their workforce is fully ready to adopt AI. 39% of CIOs and CTOs said yes. 7% of COOs said the same. (Grant Thornton, July 2026: https://www.grantthornton.com/insights/articles/advisory/2026/without-c-suite-alignment-ai-performance-sputters)

Same question. Same survey. A 32-point spread between the leader who deploys the capability and the leader who runs the operation it lands in. Neither is wrong from inside their own function. Each is working from different information, on a different timeline, with a different definition of the word “ready.” Nothing forces the two answers into the same room. Eventually a customer does.

This is the second Pillar 2 concept in the Enterprise Value Playbook. Concept 1 gave every leader a named deliverable and a KPI. This concept asks what happens where those deliverables meet. A documented strategy, accountable leaders, documented processes, trusted numbers, a shared growth plan, and better decision tools still break at the handoff when no forum exists to confirm a commitment before it crosses a functional boundary.

EVERY FUNCTION HIT ITS PLAN.​
​THE CUSTOMER STILL LEFT.

Most broken commitments do not start with a bad team. They start between two good ones, at a handoff nobody owns.

The Enterprise Value Playbook is the diagnostic I use with leadership teams to find those handoffs before a customer does. Five pillars. Twenty concepts. Each one names the signal to score, the failure pattern to look for, and the condition that tells you it is fixed.

Download the Playbook: https://sampalazzolo.kit.com/8b67fefc9f

Score Pillar 2 with your leadership team before your 2027 plan goes to the board. Reply “Playbook” with your lowest score and I will tell you where I would start.

THE PRINCIPLE

This week’s concept sits in Pillar 2, Leadership + Talent: your leadership team communicates, aligns, and coordinates across functions before a commitment ever reaches the customer.

Where You Stand

Pull the last ten commitments your company made to a customer that took two or more functions to deliver: a delivery date, a custom term, a feature, a price. For each one, ask whether every function that had to deliver it confirmed it before the customer heard it. Then count how many of the ten broke. If nobody in the room can produce the list, that is your actual score.

The Failure Pattern

Sales commits to a delivery timeline operations never agreed to. Product ships a feature finance never priced. Each function is executing competently within its own silo, and the coordination failure only becomes visible once it reaches the customer, at which point it is significantly more expensive to fix than it would have been to prevent.

The Kotter Principle at Work

Kotter’s Step 5, Empower Broad-Based Action, is the fix. Silos persist because the structural barriers between functions, misaligned incentives, no shared forum, no shared vocabulary, are never actually removed. Removing the barrier is the work. A memo asking functions to communicate better is not. Establish a standing cross-functional sync at the leadership level, focused specifically on dependencies and handoffs, not general status updates. Every commitment that crosses a functional boundary gets confirmed by both functions before it becomes a customer-facing commitment. Planning season is when every function writes its 2027 commitments at the same time: put each one that depends on another function in front of both before the plan is final.

The Win Condition

Cross-functional commitments are confirmed by both sides before they reach the customer. When a dependency conflict does surface, it surfaces in the standing sync internally, not in a customer escalation.

FROM THE CHAIRMAN

“How many customer commitments have broken because two of your functions found out about each other’s decisions after the customer did? I do not want a culture answer. I want a number.”

MARKET INTELLIGENCE

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

  1. Thoma Bravo / Proofpoint / Varonis. Proofpoint, a Thoma Bravo portfolio company, agreed to buy data security company Varonis for about $6.3 billion in cash, a 52% premium to its June 22 close. After closing, Proofpoint plans to integrate capabilities, align go-to-market efforts, and deliver a combined platform to more than 16,000 enterprises. (Thoma Bravo press release, October 15, 2026: https://www.thomabravo.com/press-releases/proofpoint-to-acquire-varonis-in-a-6.3-billion-transaction) My read: “Align go-to-market efforts” is one line in a press release. It is also where most combinations break. Two sales organizations will be selling a combined platform while two product teams are still building it and finance is still pricing it. That is this week’s failure pattern at $6.3 billion. The test for Proofpoint’s leadership is not whether the platform ships. It is whether every promise made to those 16,000 enterprises is confirmed by the function that has to keep it.
  2. GTCR + Elliott / CCC Intelligent Solutions. A GTCR-led group, with Elliott Investment Management, agreed to take CCC Intelligent Solutions private for about $6.1 billion, or $7.75 per share in cash. CCC sells software to the property and casualty insurance industry. Earlier this year, investors raised concerns about slowing growth and a slower-than-expected rollout of some newer products. (Reuters, via Insurance Journal, October 16, 2026: https://www.insurancejournal.com/news/national/2026/10/16/889163.htm) My read: A slow product rollout is rarely a product problem alone. A new product reaches a customer only when product, sales, implementation, and support all move on the same date. When one of them learns the date late, the rollout slips, and the customer is the first to notice. GTCR bought the platform. The first hundred days will show whether CCC’s leadership has a standing forum where those dates get confirmed before they become promises.
  3. Penske Corporation + Mitsui / Penske Automotive Group. Penske Corporation and Mitsui & Co. agreed to take Penske Automotive Group private at $212 per share, an enterprise value of about $16.3 billion. After closing, Penske will own about 64% and Mitsui about 36%. Roger Penske noted Mitsui has been a shareholder for 25 years. (Penske Automotive Group press release, SEC filing, October 15, 2026: https://www.sec.gov/Archives/edgar/data/0001019849/000114036126039664/ef20083688_ex99-1.htm) My read: Two owners with a quarter-century of working together now hold the entire company. That is the shared forum and shared vocabulary Kotter’s Step 5 asks for, built at the ownership level over decades. Private ownership also removes one competing timeline: the quarterly public market. The harder test sits below the board. The group runs 362 dealerships on both sides of the Atlantic, and the owners’ alignment only creates value if those operations confirm commitments with the same discipline.

SAM SPEAKS

This week I delivered “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

Thirty-nine percent (39%) of CIOs and CTOs say their workforce is fully ready to adopt AI. Seven percent (7%) of COOs say the same. Thirty-two (32) points separate the leader who deploys the capability from the leader who runs the operation it lands in.

Alignment is not a culture trait. It is a structure. A standing forum where leaders confirm dependencies and handoffs, and a rule that no commitment crosses a functional boundary until both functions have confirmed it. Without that structure, every function executes competently, and the customer is the first to see the gap.

Every deal on this week’s tape carries the same exposure. Proofpoint has promised 16,000 enterprises a combined platform and an aligned go-to-market. GTCR is buying a company whose newer products rolled out slower than investors expected. Penske and Mitsui bring a quarter-century of alignment at the ownership level to 362 dealerships that now have to coordinate below it.

Planning season puts every function’s 2027 commitments on paper at the same moment. That is the cheapest moment the year offers to reconcile them. Ask the Chairman’s question this week: How many customer commitments have broken because two of your functions found out about each other’s decisions after the customer did? If nobody in the room can give you a number, the next broken commitment is already on its way to a customer.

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

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​

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