Chase

SKILL.md

Available Context & Tools

@_platform-references/org-variables.md @_platform-references/capabilities.md

Chase

Instructions

You are executing the /chase skill. Your job is to craft a re-engagement message that breaks the silence without damaging the relationship. The message must feel human, add genuine value, and give the prospect a low-friction reason to respond. Use the 5-Layer Intelligence Model below to gather maximum context before composing.

Goal

Produce a multi-channel chase strategy that re-opens a stalled conversation. The primary output is a message tailored to the optimal channel, informed by transcript history, enrichment data, and silence duration analysis. Every recommendation must be grounded in data from the layers below.

References

Consult references/chase-templates.md for duration-specific email templates, channel-specific message formats, tone variations, and annotated good vs bad examples.

Consult references/reengagement-playbook.md for the psychology of silence, multi-channel chase sequences, when to stop chasing, multi-threading strategies, and trigger event monitoring.

The 5-Layer Intelligence Model

Work through these layers in order. Each layer informs the next.

Layer 1: Contact & Deal Context

Data to gather:

  • Contact: name, title, company, last activity date, communication preferences
  • Deal: stage, value, close date, days in current stage, owner
  • Activity timeline: last 20 activities across all channels
  • Last touchpoint: date, channel, topic, who initiated
  • Open commitments: next steps promised by either side

Via execute_action:

  • If deal_id: get_deal, get_deal_contacts, get_deal_activities (limit: 20), get_meetings
  • If contact_id: get_contact, get_contact_activities (limit: 20)

Layer 2: Enrichment

Web search for trigger events:

  • Prospect company news (funding, acquisitions, leadership changes, product launches) in last 90 days
  • Industry developments relevant to the deal context
  • Contact's recent LinkedIn activity or role changes
  • Competitor moves that create urgency

Contact enrichment:

  • Check client_fact_profiles for existing research (if research_completed_at within 7 days, use cached data)
  • Updated role, title, or company changes since last contact
  • New decision-makers or stakeholders at the account

Layer 3: Historical Context (RAG)

Search meeting transcripts for:

  • Last conversation topics and key themes with this contact
  • Commitments made by both sides ("I will send you...", "We agreed to...")
  • What excited the prospect (features, outcomes, ROI numbers they reacted to)
  • What concerned them (objections, hesitations, questions they raised)
  • Mentioned timelines or deadlines ("We need this by Q2", "Budget resets in April")
  • Competitive mentions ("We are also looking at...", "Your competitor offered...")

Use RAG results to:

  • Ground the chase message in real conversation history
  • Reference specific moments that resonated
  • Avoid re-asking questions already answered
  • Flag if no transcripts exist (first interaction vs. data gap)

Layer 4: Intelligence Signals

Silence analysis:

  • Days since last contact
  • Silence category: cooling (5-14 days), ghost (15-30 days), dormant (30+ days)
  • Risk level: low (under 7 days), medium (8-14), high (15-21), critical (22+)
  • Pattern check: Is this silence normal for deals at this stage and value?

Multi-threading status:

  • Are there other contacts at this account?
  • Has anyone else at the company engaged recently?
  • Is there a champion, economic buyer, or technical evaluator we have not contacted?

Competitive risk signals:

  • Did transcripts mention competitor evaluations?
  • Has the prospect's company posted job listings suggesting they chose another vendor?
  • Any trigger events that suggest the window is closing?

Layer 5: Re-engagement Strategy

Synthesize layers 1-4 into the optimal approach:

  • Select template tier based on silence duration (see below)
  • Choose primary channel based on engagement history and contact preferences
  • Determine tone based on relationship depth and deal stage
  • Craft the value-add based on enrichment findings (Layer 2) and transcript context (Layer 3)
  • Build escalation path if this chase does not get a response

Silence Duration Template Selection

Select the approach based on days since last contact. See references/chase-templates.md for full templates.

Duration Category Approach Tone
5-7 days Light touch Value-add nudge, share a resource or insight Warm, helpful
8-14 days Pattern break New angle, different value prop, fresh information Curious, direct
15-21 days Direct check-in Acknowledge the gap, ask if priorities shifted Respectful, clear
22-30 days Breakup Permission-to-close, last-chance framing Direct, professional
30+ days Re-activation Only if trigger event found; otherwise graceful exit Event-driven

Critical rule: Never send a 5-7 day template when 22+ days have passed. The approach must match the silence duration.

Multi-Channel Strategy

Choose the primary channel based on where the prospect previously engaged best. See references/reengagement-playbook.md for full sequences.

Channel selection logic:

  1. Check which channel the prospect last responded on -- start there
  2. If email has failed twice, switch to LinkedIn or phone
  3. If no channel history, default sequence: email (day 0) -> LinkedIn (day 3) -> call (day 5) -> text (day 7)

Channel-specific guidelines:

  • Email: 80-120 words, subject under 50 chars, single CTA
  • LinkedIn: 40-60 words, reference a shared connection or their content, no attachments
  • Call: 30-second voicemail script, reference one specific thing, leave a reason to call back
  • Text: 20-30 words, only if prior text relationship exists, ultra-casual

Email Composition

Subject Line Rules

  • Under 50 characters
  • No "Re:" tricks or fake threads
  • No "Just checking in" or "Following up"
  • Options by type:
    • Reference-based: "Quick thought on [topic from last call]"
    • Value-based: "[Relevant insight] for [their company]"
    • Trigger-event: "[Company news] -- thought of you"
    • Direct: "[First name] -- still make sense?"

Email Body Structure

Opening (1 sentence): Reference the last conversation specifically. Use RAG transcript findings. Never open with "I hope this email finds you well."

Value add (2-3 sentences): Must be grounded in Layer 2 or Layer 3 data:

  • Trigger event from web search + how it relates to their stated problem
  • Insight from transcript context (something they cared about + new development)
  • Resource, case study, or data point relevant to their specific situation

Graceful acknowledgment (1 sentence): Acknowledge the gap without blame. Tailor to the season or known context.

Soft CTA (1 sentence): Low-friction, appropriate to silence duration:

  • 5-7 days: "Would a quick call this week be useful?"
  • 8-14 days: "Happy to send over [specific resource] if helpful"
  • 15-21 days: "Has the priority shifted? Either way, no pressure"
  • 22-30 days: "Should I close this out, or is there still interest?"

Total length: 80-120 words. Chase emails must be short.

Tone Variations

Warm (default): Friendly, helpful, no pressure. Best for most situations.

Direct: Respectful but clear ask. Best when the deal was progressing well and silence is unexpected. "I want to respect your time -- is this still something you are exploring, or has the priority shifted?"

Humorous: Light, self-aware. Only for prospects with established rapport. Use sparingly.

Quality Checklist

Before returning results, verify every item:

  • Silence duration matches template tier. A 22-day gap must not use a "light touch" template.
  • Email references specific context from transcripts or CRM (not generic).
  • Value-add is grounded in data -- enrichment finding, trigger event, or transcript insight.
  • Subject line is under 50 characters and non-pushy.
  • Body is 80-120 words (not a wall of text).
  • CTA matches silence duration -- escalating directness over time.
  • Channel recommendation has a rationale tied to engagement history.
  • No guilt-tripping, desperation signals, or passive aggression.
  • Escalation path is defined -- what happens if this chase gets no response.
  • Confidence level is honest -- low if missing RAG/enrichment data, high if all layers populated.

Graceful Degradation

Failure Impact Fallback
No CRM data No deal/contact context General re-engagement email, flag as "unlinked chase"
RAG returns nothing No transcript history Use CRM activity notes only, note "no transcript context"
Web search fails No trigger events Proceed without, use CRM context for value-add
Contact not enriched No role/company updates Use last-known CRM data, suggest enrichment
No activity history Cannot calculate silence duration Ask user for context, default to "warm" 8-14 day template
Multiple contacts on deal Unclear who to chase Choose champion or last engaged, present alternatives
Contact went dark < 3 days Too soon to chase Advise waiting at least 5 business days
Conflicting signals RAG says positive, deal health says risk Surface both, let user decide approach
No email address Cannot send email Recommend LinkedIn or phone as primary channel
All channels exhausted Multiple chase attempts failed Recommend graceful exit or multi-thread to new contact

Output Contract

Return a SkillResult with:

  • data.email_subject: string (subject line, under 50 characters)
  • data.email_body: string (full message body, 80-120 words, with greeting and sign-off)
  • data.timing_suggestion: object with { best_day, best_time, timezone, wait_until, rationale }
  • data.silence_analysis: object with { days_silent, silence_category, risk_level, pattern_normal }
  • data.channel_recommendation: object with { primary_channel, rationale, secondary_channel, sequence }
  • data.multi_thread_option: object with { alternative_contact, relationship, rationale } or null
  • data.rag_context_used: array of { source, finding, relevance } objects from transcript search
  • data.confidence_level: string ("high" / "medium" / "low") with data.confidence_rationale
  • data.escalation_path: object with { next_action, timeline_days, channel, fallback_strategy }
  • data.context_used: object with { last_contact_date, days_since_contact, last_topic, contact_name }
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