AI & Infrastructure Migration Gate · CEO + CFO
The AI or infrastructure commitment is signed. The financial rules are not.
Your engineers have a migration timeline. A Snowflake deployment, a Databricks restructure, or an AI agent ecosystem built to run in parallel with your data team. Millions committed. A delivery date on the board. Without financial rules, the migration simply moves your legacy structural liabilities to faster, more expensive machinery.
I keep seeing one critical element missing from these implementation plans: nobody has defined what the new stack is obligated to return to the business. Which operational decisions it will speed up. What each individual asset inside it is permitted to cost. Who owns the decision to switch a capability off.
The commitment is already made. The month before delivery is the last clean point to define the return, the limits, and who can switch a capability off.
Scope
One month to set the rules, then quarterly review
Profile
CEO + CFO
Deliverables
Payback Rules, Keep-or-Kill Rules, Capacity Map
Format
Sessions + deliverables
No slides. Bring the migration brief and the budget approved.
01
Your engineers are building the stack. Nobody is building the financial rule set.
TL;DR
In 2026, code generation is effectively free. AI agents can spin up pipelines in hours. The carrying cost of every data asset you fail to govern correctly trends toward infinity, quietly, in payroll and in decisions that wait too long for a number nobody validated.
Read the full breakdownHide details
The engineering team presents pipeline latency figures, data freshness benchmarks, and cost-per-query projections. Every number is accurate. None of them answer the question your CFO is about to ask: what is this new stack obligated to return, product by product, and how do we know when it hasn't? The old playbook built a data team, then figured out what it was for. That sequence is how companies arrive at maintenance portfolios worth millions that nobody can shut down because nobody tracked what they were built to produce. You are about to run the same sequence at ten times the speed.
02
Three deliverables built in the foundation month, before your migration goes live.
TL;DR
Financial architecture, not a stack review. The three instruments your CEO and CFO use to evaluate every data hire, AI agent, technology decision, and product investment against a common standard, before anything is built.
Read the full breakdownHide details
- The Payback Rules. For every data product entering the new stack, we establish the explicit decision it serves, what it may cost to keep alive, and what it must return to the margin. This parameter is locked in before engineering begins, ensuring the kill decision is already defined on day one.
- The Keep-or-Kill Rules. Documented structural constraints that make build, keep, and kill choices systematic rather than political. Set now, while nobody has a favorite dashboard or tool to defend, these constraints cost a fraction of governance choices made after two years of unverified asset accumulation.
- The Capacity Map. A verified, objective picture of what your organization can actually sustain as the architecture changes: frontline skills confirmed, operational ownership defined, and fluency gaps made visible before capital is deployed, not months after adoption fails.
03
The Foundation Month
TL;DR
The engagement begins with a dedicated foundation month focused entirely on building your operational rule set: the payback rules established, the keep-or-kill constraints drafted alongside your finance and data leadership, and the capacity map verified against your actual team.
Read the full breakdownHide details
The engagement begins with a dedicated foundation month focused entirely on building your operational rule set: the payback rules established, the keep-or-kill constraints drafted alongside your finance and data leadership, and the capacity map verified against your actual team.
04
Quarterly Steering
TL;DR
Following the foundation month, we transition into a fixed-interval cadence of four strategic sessions per year. Each quarterly steering session addresses three structural questions.
Read the full breakdownHide details
Following the foundation month, we transition into a fixed-interval cadence of four strategic sessions per year. Each quarterly steering session addresses three structural questions: What capital allocation decisions did we execute this quarter and did the rules hold? What bypassed the system, and why? What requires calibration in the decision architecture for next quarter?
The output of each session is an updated set of decision criteria that the CEO and CFO use independently to govern the portfolio until the next review.
05
The Red Flag Commitment
TL;DR
At the end of month one, I provide an honest assessment of whether the operational capability transfer is taking root within your leadership team. If it is not, I tell you before you commit further capital.
Read the full breakdownHide details
At the end of month one, I provide an honest assessment of whether the operational capability transfer is taking root within your leadership team. If it is not, I tell you before you commit further capital. I put this boundary in writing because the engagement exists to protect your balance sheet, and that has to apply to my own line on it as well.
06
Built for CEOs and CFOs who have already committed to a major stack change.
TL;DR
Not for teams still deciding whether to migrate. This framework is designed exclusively for organizations where a major migration or AI stack overhaul is already fully committed.
Read the full breakdownHide details
This framework is designed exclusively for organizations where a major migration or AI stack overhaul is already fully committed: budgets are approved, engineering teams are scheduled, and infrastructure contracts are signed. If you are still in early vendor evaluation, this is not the correct moment. The operational rules we construct must match the reality of what is actively being deployed.
07
Engagement Structure
TL;DR
The scope is fixed: one foundation month, then quarterly steering. Commercial terms are set in the initial alignment call, sized to your portfolio and put in writing before any work begins.
Read the full breakdownHide details
The scope is fixed: one foundation month, then quarterly steering. The commercial terms are set in the initial alignment call, sized to your portfolio and put in writing before any work begins, including the conditions under which I will tell you to stop.
30 minutes. No slides. Bring the migration brief.
We will find the operational gap together and decide whether the financial architecture needs to be installed before your migration goes live.