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.
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:
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.
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.
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.
