Hypotheses, frames, and questions I'm working through across enterprise AI, customer success, and tech-enabled M&A. Long versions ship in the newsletter.
Most AI strategies I read inside tech-enabled businesses start in the wrong place. They start with the model, the platform, or the vendor. 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. The part of the org chart that almost always gets skipped, go in the next dispatch. Subscribe below for the long version.
// In the newsletterEach 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
Before a vendor scorecard, six questions that quietly disqualify two-thirds of the demo deck: data ownership, model provenance, deployment shape, change-management capacity, ROI defensibility, and exit cost.
// In the newsletter →A 5-factor rubric I use to defend AI use cases at the next ELT review: value bar, data readiness, operational fit, change capacity, and reversibility. Sorts decks into things you should build and things you should sequence away.
// In the newsletter →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 12 questions I run before any AI use case gets modeled: data trust, decision rights, change capacity, and the operating cadence that catches drift before it ships.
// In the newsletter →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 →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 →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 →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 →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 →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 →Two-thirds of inbound declined isn't a brand value: it's the only way the calendar stays open for engagements that pass the bar.
// In the newsletter →