upsell-sequencer

name	upsell-sequencer
description	Design usage-triggered upsell / expansion sequences (in-app + email) that fire when a customer hits a plan boundary, usage milestone, or expansion-ready signal. Use when the user says "upsell sequence", "expansion revenue", "upgrade prompts", or is designing a higher tier.
status	new

Upsell Sequencer (Revenue Squad)

Triggers expansion revenue from paid customers based on real usage signals — not calendar sends.

Triggers

• "design upsell sequence"
• "expansion revenue flow"
• "upgrade prompts based on usage"
• "we launched a new tier — how do we move existing customers"

Inputs required

1. Plan boundary definitions — seats, volume, feature-gate edges
2. Plan ladder — what's above the current plan, what's included
3. Usage event data — to fire triggers
4. Existing customer segmentation — plan, tenure, NPS, CSM assigned
5. Trigger thresholds — where does each signal fire

Process

Step 1 — Map expansion triggers

Catalog every signal that says "this customer is ready for more":

• Usage-based — approaching seat/volume limit (80%, 90%, 100%)
• Feature-locked — they tried to use a Business-tier feature on Pro
• Value-realized — hit N activations or milestones (happy = willing to pay more)
• Team growth — 2+ new users added in 30 days
• Case study worthy — NPS 9+ AND 90+ days retained

Each trigger fires its own sub-sequence.

Step 2 — Design by trigger type

Usage approaching limit:

• Day 0 (80%): in-app banner "you're at 80% of your monthly quota"
• Day 3 (90% or still climbing): email "here's what you'll save on the annual Business plan"
• Day 7 (100%): hard gate + direct upgrade CTA + chat option

Feature-locked:

• In-product: locked feature modal with preview + "upgrade to unlock" CTA
• Email 3 days later if they haven't upgraded: "here's what that feature unlocks — a case study"

Value-realized (happy signal):

• Email: "you're in the top 20% of users. Teams at this usage level often upgrade to X for Y. Want to try free for 14 days?"

Team growth:

• In-app to admin: "your team grew from 3 → 5 seats. Pro charges per seat; Business is flat-rate past 10 — math attached."

Step 3 — Write the copy

For every message:

• Lead with value shown, not feature listed
• Include the math — explicit saving or capability gain
• One CTA, one path, no branching

Step 4 — Rules of the road

• Never upsell someone in their first 30 days (they haven't earned the right to be asked)
• Never upsell someone with an open support ticket > 48h
• Never upsell right after a pricing change — 60-day cool-off
• Cap: no more than 2 upsell messages in a 30-day window per customer

Step 5 — Instrumentation + metrics

• upsell_trigger_fired (type, user_id, plan_from, plan_to)
• upsell_cta_clicked
• upsell_converted
• expansion_arr

Primary metric: expansion MRR from this flow. Guardrails: churn rate in users who received upsells, unsubscribe rate.

Output artifact

upsell-sequences.md with:

• Trigger catalog
• Per-trigger flow + copy
• Rules of the road
• Metrics spec
• Hypothesis per sequence

Handoff

• In-app → product
• Emails → Lifecycle Email Designer
• Expansion ARR → Revenue Dashboard Builder
• Hypotheses → A/B Test Designer

Example call

"Build our upsell sequences. We have Pro ($29/seat) → Business ($99/flat up to 25 seats, then custom). Trigger on 80% seat utilization and when team hits 10+ seats. Usage data in events.csv."