Working notes from the engagement.
Hypotheses, frames, and questions I'm working through — enterprise AI, customer success, Salesforce, software M&A, fractional leadership, and the operating decisions tech-enabled businesses actually face. Long versions ship in the newsletter.
Enterprise AI is a customer problem before it's a model problem.
Most AI strategies I read inside tech-enabled businesses start in the wrong place. They start with the model, the platform, or the vendor — when the question that actually compounds is which customer outcome the company is trying to change.
The four conditions that have to be true before any model goes live in a customer-facing process — and the part of the org chart that almost always gets skipped — go in the next dispatch. Subscribe below for the long version.
// In the newsletterWorking perspectives, drawn from two decades of the work itself.
Each entry is a working take — a frame I'd talk through with a CEO, sponsor, or operating team. Drawn from real engagements; long versions ship in the newsletter.
// TOPICS COVERED: AI & Data · Customer & GTM · Salesforce · M&A · Vendor Diligence · Sales Enablement · Principal POV
AI readiness is a customer-process question, not a model question.
The 12 questions I run before any AI use case gets modeled — covering data trust, decision rights, change capacity, and the operating cadence that catches drift before it ships.
// In the newsletter →Renewals and CSAT are the floor. Revenue lift is the ceiling.
What CFOs are now asking customer-success leaders to prove — and how the strongest CS teams are answering with productivity, expansion, and operating-leverage metrics.
// In the newsletter →The Salesforce second wave in energy isn't more dashboards — it's customer-record ownership.
Trading, services, and retail are still arguing about who owns the customer. Data Cloud and Agentforce only matter once that fight is settled inside the org chart.
// In the newsletter →TSA failures aren't legal. They're knowledge-transfer failures dressed in legal language.
A working list of what actually has to be written down before day one — organized by what survives the asset transition versus what evaporates the moment the email aliases turn off.
// In the newsletter →How you pick a vendor reveals your operating discipline. Treat selection as the strategy itself.
What I look at on systems-integrator and AI-partner scorecards. What I no longer trust on first read. Why the RFP isn't the diligence — it's the tell.
// In the newsletter →Three signals leadership teams should watch — six months before they call a fractional executive.
Most teams call too late. The early indicators surface in revenue forecasting accuracy, customer-escalation patterns, and the half-life of executive decisions before they're re-litigated.
// In the newsletter →The 90-day seller window is fixed. Curriculum design is what determines time-to-revenue.
Why most onboarding programs fail the seller's calendar — and the placemat architecture that turns hire-date into revenue-date inside 12 weeks, harmonized with the firm's broader transformation.
// In the newsletter →Marketing, sales, and CS still operate as three companies inside one P&L.
The case for collapsing them on the way to scale — what changes in incentives, what changes in tooling, and what changes in the customer experience when the seams disappear.
// In the newsletter →Saying no is the operating decision that keeps an independent practice useful.
Two-thirds of inbound declined isn't a brand value — it's the only way the calendar stays open enough to do real work for the engagements that pass the bar.
// In the newsletter →