What success looks like at 30, 60 and 90 days
Define success before the engagement starts, in observable milestones: by day thirty the ICP and pipeline stages exist and the forecast is real; by day sixty discovery is installed and a founding deal is moving on the new playbook; by day ninety the cadence runs without the founder in the room.
Day 30. A written ICP with disqualifiers and the trigger event. Pipeline stages with exit criteria in the CRM. A forecast built bottom-up from the deals, with a confidence rating per deal. A weekly pipeline review that happened three times.
Day 60. A discovery question set the whole team uses. Qualification discipline that has already killed at least one no-decision deal. Positioning a prospect has repeated back unprompted. One founding enterprise deal advanced through the new stages, with the founder watching rather than driving.
Day 90. The same deal won twice more on the same playbook, or a clear diagnosis of why not. A hiring scorecard and the first account-executive interviews under way. Board reporting that Finance signs. The cadence run by someone other than the founder or me for two consecutive weeks.
The number. Pipeline coverage and win rate move before revenue does. I commit to leading indicators at ninety days and to the revenue outcome at the horizon the sales cycle allows; a promise of bookings at ninety days on a nine-month enterprise cycle is a promise nobody can keep.
How it is measured. One page, three columns: the milestone, the evidence, the date. The same page is the basis for the hand-off to a full-time leader when the time comes.
How I work
Three ways to engage — the two-week diagnostic, the ninety-day foundation, the retained seat — and the terms in one paragraph.
Open »The Revenue Diagnostic
Thirty questions across six pillars, including the one nobody else scores: the AI agents already in your revenue engine. A score, three findings and a ninety-day plan.
Run the diagnostic »New essays and operator tools, as they publish.
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