Catch the upgrade-ready moment, not the next renewal call

Create an AI-derived attribute 'usage_capacity_used' on the Account object. For each metered usage dimension on the account's current plan (API calls / contacts / events / seats / storage / sends), compute current_usage / plan_limit as a fraction. Output: the maximum across all dimensions (the bottleneck), with which dimension is at threshold. Flag thresholds: 0.8 = approaching, 0.95 = near-limit, 1.0+ = over-limit (overage charges or service throttling).

Build a segment 'Upgrade-ready accounts' capturing paying accounts where usage_capacity_used >= 0.8 AND the account isn't already on the highest plan AND no upgrade conversation occurred in last 30 days. Splits implicitly: (a) approaching (0.8-0.94) → in-app prompt, (b) near-limit (0.95-1.0) → in-app prompt + AE task, (c) over-limit → urgent AE task + customer notification.

Generate in-app upgrade prompt content. Personalized to which dimension is approaching limit: 'You've used 84% of your monthly events on the Starter plan. Upgrade to Pro for 10x capacity + advanced reporting.' Include current usage stat, plan comparison, and a one-click upgrade CTA. Tone: helpful (we noticed) not pushy (we're charging you). Suppress display for users not in plan-decision-maker role (avoid spamming end users about upgrades they can't approve).

Create a workflow firing when usage_capacity_used crosses 0.8 (and on each subsequent threshold). Step sequence: (1) trigger in-app upgrade prompt for plan-decision-makers on the account; (2) for accounts with MRR > $500/month, create AE expansion task immediately (don't wait for prompt-clickthrough — these are high-value, deserve human outreach); (3) for over-limit cases, additionally send an email notification to billing-contact about overage; (4) emit upgrade_signal event for analytics tracking. Throttle: don't re-fire for the same account within 14 days even if it's still over threshold (avoid prompt fatigue).

Compose an upgrade conversion dashboard: usage-trigger volume per week (accounts crossing 0.8 threshold), in-app-prompt-to-upgrade conversion rate, AE-task-to-upgrade conversion rate (for high-MRR cohort), ARR uplift from usage-based expansion this quarter, and median time from threshold-cross to upgrade-completed. Compare upgrade-via-prompt vs. upgrade-via-AE-outreach as motion-effectiveness signal.