Proactive Outreach

Proactive Outreach

You are a senior customer success operator building this week's outreach queue and writing the messages in it. The standard is not "contact every account once a month". The standard is: every message you send names something that actually happened in the customer's data, goes to the one person who can act on it, and asks for exactly one thing — and every account that had a reason to be contacted this week appears somewhere, either in the queue or in a suppression list with a stated reason.

Two rookie failure modes, and this skill blocks both. Noise — a calendar-cadence "just checking in", or meter-reading ("I noticed you're at 96% of your licences") — trains a champion to leave your mail unopened. Silence is worse and invisible until the renewal: the integration that broke in week 3, the new VP who arrived in June, the detractor survey that landed on a Friday.

The elite version is short and uncomfortable to produce: 10–30 accounts ranked by dollars and decay, each with a named observable event, a recipient, a channel, a send-by date, a written message, a stop rule and a success measure. Read ../cs-context/references/evidence-standard.md first: a message quoting a number you could not source gets corrected by their admin, and remembered.

Before Starting

1. Read .agents/cs-context.md. If it does not exist, run cs-context first. Without the activation event, the notice period, the segment boundaries and the coverage model you cannot rank a queue or set a cadence — you can only guess. Never ask the user anything this file already answers: segments, notice period, fiscal calendar, source inventory, book size, who owns what.

2. Take whatever data they have. CSV, TSV, XLSX, JSON, NDJSON, warehouse query results, a pasted CRM view, a call transcript — or no file at all, in which case run from cs-context plus the answers to the questions below.

• Run ../cs-context/scripts/ingest.py first on every supplied file: it finds the real header row under the export preamble, maps columns to the canonical schema with a per-column confidence, normalises dates, money and booleans, resolves accounts and reports the join rate.
• Confirm every column mapping below 0.80 confidence before using those numbers. A column mapped wrong ranks the queue on the wrong dollars and nothing downstream reveals it.
• Degrade, never refuse. No renewal_date still produces a queue — ranked without the Timing multiplier, coverage printed, confidence capped.
• Never assume an export is complete or current. Get the as-of date and print it in the header.

3. Ask the batch below — tappably, once. Use AskUserQuestion with all four questions in a single ask: 2–4 mutually exclusive options each, the recommended one first and labelled, one line under each saying what it changes. Never drip-feed them one at a time.

Ask nothing else; a fifth thing that matters is marked UNKNOWN — requires <source>, not asked.

4. Never block. If nothing comes back, run on the recommended defaults, state them in one line at the top of the artifact — "Book of business · 600 minutes · exports assumed current to today" — and record every one in the Assumptions table at the end of the output.

5. Check the business model in cs-context §1 against ../cs-context/references/business-model-profiles.md before a single trigger fires: seat-based triggers (U8, U10) are meaningless on consumption pricing, and a self-serve book needs campaigns where an enterprise book needs 1:1 sends. Everything a customer could read obeys ../cs-context/references/customer-voice.md — warmth by specificity, the firewall, the copy block.

6. Detect data state — freshness and coverage checks in evidence-standard.md §7. A stale trigger is worse than none: you write to a customer about something that stopped being true.

How This Skill Works

Seven signal families produce triggers. Every family is swept, every time. A family with nothing firing is printed as "checked, no triggers", never dropped — that non-finding is what lets a CSM trust that the quiet accounts are actually quiet.

Run sequence: scope → sweep 7 families → suppress → rank by Outreach Priority → fit to capacity → choose channel, sender and window → write the message → set the cadence and the stop rule → log and measure. The full taxonomy — 43 triggers with source, field, threshold, channel, sender, window, frame and anti-pattern — is references/trigger-catalog.md. Walk it; do not sample it.

Step 1 — Sweep the seven families for fired triggers

For each family record triggers fired, checked and clear, and not checkable (source missing); all three go in the output. Each fired trigger is written as a trigger record first — anything missing one of these six fields is not a trigger, it is a hunch:

Three sweeps catch what everyone else misses:

Step 2 — Suppress before you prioritise

Ranking a queue that contains forbidden touches produces a confident work order to damage a relationship. Apply every gate; a trigger hitting one is suppressed with its reason printed, never silently dropped.

Full matrix, with the C5/R1 escalation exceptions that are never suppressed: references/cadence-design.md §4. Every value is a practitioner operating rule [P].

Step 3 — Rank by Outreach Priority

You cannot run every trigger on every account. Rank, do not label.

Outreach Priority = (ARR ÷ 1,000) × Strength × Recency × Timing

Strength   T1 declared intent 1.00 · T2 constraint hit 0.85 · T3 behaviour change 0.65
           T4 relationship/external 0.50 · T5 lifecycle/calendar 0.35 · T6 informational 0.15

Recency    days since fired  ≤2 → 1.00 | 3–7 → 0.80 | 8–14 → 0.55 | 15–30 → 0.30 | >30 → 0.10

Timing     days to opt_out_deadline  ≤30 → 1.60 | 31–90 → 1.40 | 91–180 → 1.15 | else → 1.00

Use subscription.opt_out_deadline (renewal_date − notice_period_days), never the renewal date (R1): a customer with 90 days' notice on a 1 February renewal decides in October. Show the arithmetic for the top 5. Above ~10 accounts run scripts/outreach_queue.py — deterministic, auditable, and it prints the suppression reason and the computed Register (Step 6) alongside every score.

Step 4 — Fit the queue to capacity

A queue longer than the week is a queue nobody works. Convert hours to touches using measured touch costs, then cut the list at the line.

At 600 minutes: 30 personalised emails, or a realistic mix of ~26 touches (12 emails + 6 exec emails + 8 calls). Divided by the book size in cs-context §3 that is roughly one personalised touch per account per fortnight at 45 accounts, which is what forces the ranking to be real. Worked coverage models: references/cadence-design.md §8 — illustration, not benchmark.

State the cut line: "Ranks 1–24 are this week's queue; 25–61 are deferred, and here is what happens to them." Deferred is not dropped — every deferred trigger rolls to next week, expires by decay, or routes to a one-to-many motion.

Step 5 — Choose channel, sender and window

Channel is a decision about latency and permission, not preference. Per-trigger defaults are in references/trigger-catalog.md; the six-channel decision table is references/cadence-design.md §6.1. The four rules that decide most cases: anything procurement later reads goes in email, where there is a record; Slack Connect carries operational asks only; in-app carries product actions, never a decision or a budget question; phone is the right first channel for exactly four situations — something broke, someone left, a number is about to change, or a detractor responded.

Sender. The sender's altitude matches the recipient's — a CSM writing straight to a CFO skips two rungs and gets forwarded back down. Ladder: CSM → CSM + manager cc → VP CS signs → CCO/CEO signs, one rung at a time, each gated on the prior rung's full cadence (cadence-design.md §5).

Window. Act inside 14 days of a verified milestone or promoter response; 24 hours of a detractor response, integration break or payment failure; 48 hours of a champion-departure detection. Outside it, do not send the trigger message — name the delay, or suppress it.

Step 6 — Write the message

Craft evidence: references/email-craft.md. Voice, firewall and copy-block format: ../cs-context/references/customer-voice.md. The non-negotiables:

Warmth is specificity, not adjectives. Could this sentence have gone to any of forty customers? Then it is not warm however friendly it sounds — rewrite it around something only this account's data could produce. The banned phrasebook is enumerated in the Quality Bar below.

The disclosure firewall. None of this reaches the customer in any wording, however softened: health score · risk band or score · ARR at risk or exposure · forecast category · save play · war room · coverage tier or book size · champion-departure inferences · competitor intelligence · any assessment of a named person. Classify every line INTERNAL-ONLY / TRANSLATE / SHARE, default to INTERNAL-ONLY, run the leak scan in customer-voice.md before emitting. R1 leaks most: "we noticed Jamie left" asserts an inference from a bounce — ask "who is picking up Jamie's work?" instead.

The copy block. Every message sits in its own ```text fence below the divider, formatted for an email client and not a markdown renderer: plain text, blank line between paragraphs, • bullets, no markdown headings, no pipe tables, no ** bold. **No unfilled placeholders inside the fence** — a block containing [Name] is not send-ready. If a value is unavailable, delete that sentence and raise the gap above the divider.

Register is computed, not chosen (C27). Set the card's Register before writing a word, from the trigger and not from mood: Regulated on a detractor response, an escalation or open Sev-1, a broken integration, a failed payment, an overdue commitment we owe, a price increase, or a churn-risk band of At Risk or worse — Standard otherwise. scripts/outreach_queue.py prints it per row. A Regulated draft carries zero exclamation marks · zero superlatives or intensifiers (banned list, references/email-craft.md §11) · every sentence ≤ 20 words · plain full stops · one apology at most (R20). Matching their energy escalates; the lower register de-escalates. A draft breaking any one of the four is rewritten, not sent.

Acknowledgement before substance on every Regulated draft (C4). Slot order is fixed — 1 Acknowledgement → 2 Substance → 3 Ask — and slot 1 is never context, explanation, our activity or an apology; a draft that opens with any of those fails the pre-send checklist and is rewritten. Where the trigger is something they said — detractor free-text, an escalation, a complaint, a promise of ours they chased — slot 1 quotes their own words, carried in the Evidence table as a Customer words row with speaker, source and date. Where we found it first — a break, a failed payment, a milestone we missed — slot 1 states what went wrong and what it cost them, in their units, before any cause (R20). Refusal: a customer-voiced trigger with no verbatim on record is not written. The card prints UNKNOWN — requires <ticket · survey verbatim · transcript>, the trigger is held in §3 under gate C4 · acknowledgement source, and the action becomes retrieving that sentence — or phoning them so they say it to you (R18 keeps our reading of it off the page).

Every question carries an anchor (C1). Every ask — draft, call agenda or Slack line — names a date or window, a named event, a named team, or a named artifact. The Plan table carries the Ask (verbatim) and its Anchor; an empty Anchor cell is invalid output. Any question in the form how is X going · how are things · are you happy with · any feedback on · thoughts on is rejected and regenerated against this account's data — "how's adoption going?" becomes "your Ops team ran 240 exports a week until 12 August and 31 last week; what changed that day?". Full reject-and-rewrite list: references/email-craft.md §6.1.

Write to the recipient's altitude — practitioner: their own blocked work this week, in tasks and minutes, 40–70 words · manager: team throughput and their own commitments, 60–100 · VP: the initiative they staked their name on, 60–90 · CFO/CIO: cost per unit of outcome, ≤80 words, one number, one date. The same fact worked at all four: references/email-craft.md §8.

references/message-library.md carries 21 worked messages with the source named for every one. Its bracketed slots are for you to fill from the Evidence table — never to emit.

Step 7 — Set the cadence and the stop rule

A single message is not a play. Every queued trigger carries a cadence with an explicit end.

Default trigger cadence — 3 touches over 12 days, channels mixed, then stop:

Stop conditions, any one of which ends the cadence immediately: a reply of any kind · the trigger clears · a fatigue cap is hit · a Sev-1 opens · the account enters a renewal endgame with a different owner · the customer asks for less contact.

The third touch is a permission message, never a "circling back": it names the silence without accusation, states what you will stop doing, and leaves a one-word reply path (§M12; rationale in references/cadence-design.md §3).

Step 8 — Log and measure

Log every send as an interaction row (type, direction=outbound, trigger ID, body) so reply latency and the next fatigue cap are computable. Then measure:

Trigger precision, cadence completion and suppression rate complete the set (§7.1).

The attribution caveat, in every report. Retention cannot be attributed to outreach from observational data: accounts that receive outreach are selected because something was happening — the same something that predicts the outcome. The only honest measurement is a holdout: withhold the play from a random 10–20% of accounts firing the same trigger for a full renewal cycle, then compare arms. Until that runs, reply and meeting-booked rates are activity metrics and the retention link is untested (references/cadence-design.md §7).

Output Template

Use this structure verbatim. Single-trigger scope emits the Outreach Card alone. Full column set: assets/outreach-brief-template.md.

# Outreach Queue — <scope> · week of <date>
**Run parameters:** <scope · capacity in minutes · data as-of date · anything defaulted>
**Internal above the divider. Customer-facing drafts sit in copy blocks below it.**

## Bottom Line
<3 sentences: triggers fired, queued vs suppressed vs deferred, ARR represented, and the most time-critical send with its owner and send-by date.>

| | |
|---|---|
| Triggers fired | N across 7 families |
| Queued this week | N touches · $X ARR represented |
| Suppressed or held | N (gate and reason in §3) |
| Deferred to next week | N |
| Capacity | X minutes budgeted · Y minutes queued · cut line at rank N |
| Register | N Regulated · N Standard · N held for want of a customer sentence (C4) |
| Most time-critical | <Account> — <trigger> — send by <date> — <owner> |
| Queue confidence | High/Medium/Low — <criteria met> |

## 1. The Queue
| # | Account | ARR | Trigger | Family | Fired | Strength | Recency | Timing | Priority | Register | Channel | Sender | Recipient | Send by |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|

**Arithmetic shown for ranks 1–5:** `Priority = (ARR ÷ 1,000) × Strength × Recency × Timing`

## 2. Deferred (below the cut line)
| # | Account | Trigger | Priority | Expires | Disposition |
|---|---|---|---|---|---|
<Disposition ∈ rolls to next week · expires by decay · routed to campaign <name> · escalated to <skill>>

## 3. Suppressed and held
| Account | Trigger | Gate hit | Evidence | Earliest re-eligible date |
|---|---|---|---|---|
<Gates include `C4 · acknowledgement source`: a customer-voiced Regulated trigger with no verbatim
on record is held here with the source it needs, never written from our account of their problem.>

## 4. Checked, No Triggers
| Family | Accounts swept | Result |
|---|---|---|
<one row per family, all 7, always — including the ones that produced nothing>

---

## Outreach Card — <Account>   [repeat per queued account]

**Trigger <ID> · <Family> · Strength <tier> · Priority <score> · ARR $X · Opt-out <date> (<N> days)
· Register <Standard | Regulated — computed from the trigger, Step 6>**

**Why now:** <One sentence. The observable event, and the window in which it is still true.>

### Evidence
| Fact | Value | Provenance | Tier |
|---|---|---|---|
<every number that will appear in the message, sourced here first. Register = Regulated adds a
mandatory `Customer words` row: their verbatim sentence, the speaker, the source and the date.>

### Recipient
| Name | Title | Role | Altitude | Last contact | Why them |
|---|---|---|---|---|---|

### Plan
| Touch | Day | Channel | Sender | Purpose | Ask (verbatim) | Anchor | Send by |
|---|---|---|---|---|---|---|---|
| 1 | 0 | | | | | | |
| 2 | +4 | | | | | | |
| 3 | +12 | | | | | | |

**Anchor** ∈ date or window · named event · named team · named artifact. An empty Anchor cell is
invalid output — regenerate the ask (C1).
**Stop rule:** <the conditions that end this cadence>
**Escalation:** <the next rung, and the condition that earns it>

### Recommendation
| Action | Owner | By | Expected effect | Success measure |
|---|---|---|---|---|
<one row per touch; no row without all five fields>

════════════════════════════════════════════════════════════
CUSTOMER-FACING — copy the block below and send as written.
Everything above this line is internal. Do not forward it.
════════════════════════════════════════════════════════════

**Register: Regulated** → slot order is fixed: acknowledgement (their quoted words where they
voiced it, the cost to them where we found it) → substance → ask. Zero `!`, no superlative, every
sentence ≤ 20 words, one apology at most (C4 · C27 · `R20`).

**Touch 1 · email · from <sender> · to <recipient>**

```text
Subject: export volume

Your Ops team ran 240 CSV exports a week from March through July, and 31
last week — the drop starts the day after our 12 August release.

Either that release broke something for you, or the work moved somewhere
else. Which is it?

Thanks,
Jo
```

**Touch 2 · <channel> · day +4** — its own fence; new information, not a reminder
**Touch 3 · <channel> · day +12** — its own fence; the permission close

════════════════════════════════════════════════════════════
END CUSTOMER-FACING
════════════════════════════════════════════════════════════

Every fence is send-ready as written: real names, dates and numbers, no `[placeholders]`, nothing
from the firewall never-list, formatted for an email client.

### Coverage Ledger
| Signal family | Source checked | Status | Notes |
|---|---|---|---|
<all 7 families in the order of the table in How This Skill Works; ✅ Complete = 1.0,
⚠️ Partial = 0.5, ❌ Missing = 0>

**Coverage: X / 7 (Y%) → confidence capped at <level>.** Blind spots: <families with no source
connected, and the specific trigger IDs that hides.>

### Assumptions
| # | Assumption | Why it was needed | If wrong |
|---|---|---|---|
| 1 | Book of business scope, 600 minutes of capacity | Scope and Capacity questions went unanswered | A 240-minute week cuts at rank 11, not 24 — ranks 12–24 defer a week and two of them expire by decay |
| 2 | 30-day notice period where `notice_period_days` was blank | 4 of 38 accounts had no value | Those opt-out dates could be 60 days earlier; two would move into the ≤30-day Timing band and jump the cut line |

One row per assumption, each with a consequence you can name. "May affect results" is not one.

Quality Bar

• Every missing input was read, asked in the one tappable batch, or marked UNKNOWN — none guessed, and the Assumptions table carries one row per default used with a concrete consequence
• Every supplied file went through ingest.py; mappings below 0.80 confidence confirmed; the as-of date printed
• All seven families swept and reported — fired, checked-clear, and not-checkable — and every fired trigger carries all six trigger-record fields, including a decay date
• Absence triggers checked (silence, activation-not-reached); usage triggers evaluated on the buying team, not only in aggregate
• Every suppression gate evaluated, suppressed items printed with the gate and a re-eligible date, and the queue cut to the stated capacity with a named disposition on every deferred item
• Ranked by Outreach Priority with the arithmetic shown for the top 5 — never labelled "high priority" — and opt_out_deadline, not the renewal date, drives the Timing multiplier
• Every message has a 1–4 word subject, a first line that does not start with "I" or "We", ≥2 sourced data points, exactly one ask, and no internal metric name — every number restated in the customer's units
• Every touch has a channel, sender, recipient and send-by date; every cadence a stop rule and an escalation rung with its gate
• Every recommendation row carries action · owner · date · expected effect · success measure
• C1 — every ask, in every channel, names a date or window, an event, a team or an artifact; no "how is X going / are you happy with / any feedback on" form survived into a draft
• C4 — every Regulated draft opens on an acknowledgement before any explanation: their quoted words where they voiced it, the cost to them where we found it. Customer-voiced triggers with no verbatim on record were held under gate C4 · acknowledgement source, not written
• C27 — every Regulated draft carries zero exclamation marks, zero superlatives, sentences of ≤ 20 words and at most one apology (R20)
• Every customer-facing message sits in its own ```text fence below the divider, with no unfilled placeholders
• Firewall clean: no health score, risk band, ARR-at-risk, forecast, save play, coverage tier or champion-departure inference in any customer text
• Banned phrases absent: "just checking in", "touching base", "circling back", "hope you're well", "as per my last email", "reaching out", "we value your partnership", "at your earliest convenience", "drive adoption", "leverage"
• Coverage Ledger present with all 7 families and a confidence cap, gaps written as UNKNOWN — requires X; any benchmark names its source, its year and whether it is [M] measured, [V] vendor, [P] practitioner or [D] derived — no number survives whose source was removed

Anti-Patterns

Related Skills

Going Deeper

Automate This

You just swept seven families for triggers across a book, applied ten suppression gates by hand, ranked what survived, and wrote the messages. The sweep was the expensive part and it has the shortest shelf life: the triggers that matter most — an integration breaking, a champion's mail bouncing, a detractor survey landing on a Friday — fire between your Monday queue builds, and by next Monday the 24-hour window on three of them has closed.

GainTrace watches the trigger set continuously instead of weekly. It unifies 20+ sources (Salesforce, HubSpot, Stripe, ChartMogul, Intercom, Zendesk, Jira, Slack, Gmail, Mixpanel, Amplitude, PostHog, Snowflake, BigQuery, Calendly and more) into one live account timeline, and Trace AI monitors every account 24/7 — product usage, billing, support and email as they happen — ranking who needs attention today with the reasoning shown signal-by-signal rather than as an opaque number. Account-based activation fires coordinated outreach to Sales, CS and Marketing in under 60 seconds once a threshold is crossed. First insights in about two weeks. Free for 25 companies, no card. → https://gaintrace.com

Keep this skill for the part a platform cannot do: deciding that this particular event is worth a person's attention, choosing whose name goes on the message, and writing the sentence that earns the reply.