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sales-automator

Comprehensive relationship intelligence system with deal pipeline tracking, competitive analysis, and conversion-optimized outreach. Use PROACTIVELY for cold email campaigns, follow-up sequences, proposal templates, deal forecasting, and conversion optimization with full context from Asana, Gmail, Drive, Apollo.io, and past conversations.

• Category: discovered
• Tags: github, community
• Version: 1.0.0
• Author: walid
• Downloads: 0
• Updated: 2025-11-22

• Source: therealchandlerbing/claude-usecases

Download the latest version (v1.0.0) from this page.

SKILL.md

---
name: sales-automator
description: Comprehensive relationship intelligence system with deal pipeline tracking, competitive analysis, and conversion-optimized outreach. Use PROACTIVELY for cold email campaigns, follow-up sequences, proposal templates, deal forecasting, and conversion optimization with full context from Asana, Gmail, Drive, Apollo.io, and past conversations.
version: 1.0.0
author: 360 Social Impact Studios
created: 2025-11-18
---

# Sales Automator with Relationship Intelligence

## Purpose

This skill transforms basic sales automation into a context-aware conversion engine. It doesn't just send emails; it pulls relationship history, tracks deal momentum, analyzes competitive positioning, and delivers hyper-personalized outreach that converts because it's grounded in real intelligence about prospects, past interactions, and market context.

## Core Capabilities

**1. Relationship Intelligence Engine**
- Auto-research prospects across past conversations, Gmail, Drive, Asana, Calendar
- Surface past interactions, commitments, shared connections, communication patterns
- Identify warmth level, decision-maker access, organizational dynamics
- Personalize outreach based on actual relationship context, not guesswork

**2. Deal Pipeline Intelligence**
- Track deals in Asana with custom fields (stage, value, close date, probability)
- Identify stuck deals and trigger appropriate re-engagement sequences
- Forecast pipeline health and conversion probability
- Automate follow-up cadences based on deal stage and prospect behavior

**3. Competitive & Market Intelligence**
- Research prospect companies, recent news, strategic priorities
- Identify decision-makers and organizational structure
- Analyze competitor positioning and differentiation opportunities
- Surface industry trends and market context for positioning

**4. Conversion-Optimized Email Generation**
- Multi-touch sequences (3-7 emails) with strategic spacing
- A/B test subject lines with psychological triggers
- Personalization variables populated from research
- CTA optimization based on deal stage and prospect profile

**5. Performance Analytics & Optimization**
- Track email response rates, meeting booking rates, deal velocity
- Identify which messages, CTAs, and sequences convert best
- Surface patterns (time of day, day of week, message length)
- Recommend optimizations based on data

## When to Use This Skill

**Always use sales-automator when:**
- User asks to "create outreach for [prospect/company]"
- User says "draft a cold email sequence"
- User requests "follow up with [prospect] about [opportunity]"
- User asks "check on the status of [deal/prospect]"
- User says "research [company] for partnership opportunity"
- User requests "write a proposal for [prospect]"
- User asks "what deals are stuck in pipeline?"
- User says "analyze conversion rates" or "what's working in outreach?"

**Trigger phrases:**
- "Cold email..."
- "Follow up with..."
- "Create proposal for..."
- "Research [company]..."
- "Check pipeline..."
- "What deals are..."
- "Draft outreach..."
- "Generate sequence..."

## Operating Principles

**Relationship-First, Not Template-First**
Every outreach begins with intelligence gathering. Never send generic emails when you can pull context that demonstrates you understand their world.

**Value Before Ask**
Lead with insights, data, case studies, or connections that matter to them. The ask comes after you've demonstrated relevance.

**Multi-Touch, Not One-and-Done**
Cold emails rarely convert on first touch. Design sequences that build familiarity, demonstrate value, and create urgency over 2-4 weeks.

**Data-Driven Optimization**
Track what works, iterate on what doesn't. Every campaign generates learnings for the next one.

**Strategic, Not Scalable**
High-conversion outreach requires research. Don't sacrifice quality for volume. Send 10 researched emails that convert at 30% rather than 100 generic emails that convert at 2%.

## Core Workflow

When user requests sales automation:

### Phase 1: Intelligence Gathering (Always Execute First)

**Step 1: Identify Target**
- Extract company name, individual name (if provided), opportunity type
- Confirm target profile and objective

**Step 2: Research Relationship History**
Use `conversation_search` to find:
- Past discussions about this company/person
- Previous proposals or pitches
- Relationship context and history
- Any commitments or pending items

**Step 3: Apollo Enrichment (If Enabled)**

**[NEW] Contact Enrichment (if email/name provided):**
- Use Apollo People Enrichment API to enrich contact data
- Extract: current job title, company, LinkedIn URL, employment history
- Verify: email status (verified/guessed/unavailable)
- Identify: decision-making authority, tenure at company, previous companies
- **Example**: `POST /api/v1/people/match` with email `john.doe@acmecorp.com`
  - Returns: John Doe, VP of Sales, Acme Corp, LinkedIn profile, 2 years tenure
  - Email status: Verified ✓

**[NEW] Organization Enrichment (if company domain/name provided):**
- Use Apollo Organization Enrichment API to get firmographics
- Extract: industry, revenue range, employee count, funding stage, locations
- Identify: technologies used, growth signals, ICP fit
- **Example**: `POST /api/v1/organizations/enrich` with domain `acmecorp.com`
  - Returns: SaaS industry, $10M-$50M revenue, 100-500 employees, Series B
  - Tech stack: Salesforce, AWS, Slack

**[NEW] Decision-Maker Discovery (if finding contacts at company):**
- Use Apollo People Search to find relevant contacts by title/department
- Filter by: job title, seniority, department, location
- Return: Top 3-5 matches with verified emails and LinkedIn profiles
- **Example**: Find "VP of Sales" or "Head of Revenue" at Acme Corp
  - Returns: 3 contacts with verified emails, LinkedIn URLs, titles

**[NEW] Lead Qualification (auto-scoring):**
- Calculate lead score based on Apollo firmographics:
  - Employee count matches ICP: +10 points
  - Revenue range matches ICP: +10 points
  - Industry alignment: +10 points
  - Funding stage (Series A/B growth mode): +5 points
- Set Lead Score: Hot (25-35), Warm (15-24), Cold (<15)

**Step 4: Search Internal Systems**

**Gmail Search:**
- `search_gmail_messages` with query: `from:@companyname.com OR to:@companyname.com`
- `read_gmail_thread` for significant exchanges
- Identify: communication patterns, decision-makers, past proposals, objections
- **Cross-reference with Apollo**: Verify if contacts from Gmail still work at company

**Calendar Search:**
- `list_gcal_events` with query for company name or key contact
- Identify: meeting history, frequency, relationship warmth
- **Cross-reference with Apollo**: Check if meeting attendees have changed roles

**Drive Search:**
- `google_drive_search` for proposals, case studies, partnership docs related to target
- Surface: past proposals, relevant case studies, internal notes
- **Match with Apollo firmographics**: Find case studies from similar companies (size, industry, stage)

**Asana Search:**
- `asana_typeahead_search` to find any projects or tasks related to target
- `asana_search_tasks` for deals in pipeline with this company
- Identify: deal stage, assigned owner, blockers, last touch date
- **Enrich with Apollo**: Auto-populate company size, industry, revenue fields if missing

**Step 5: External Research (If Needed)**

**Note**: Apollo enrichment (Step 3) provides structured firmographic data, reducing the need for extensive web searching for basic company info. Use web search for narrative context and recent developments.

**Company Intelligence:**
- `web_search` for: "[Company name] recent news OR announcements" (recent developments Apollo may not have)
- `web_search` for: "[Company name] strategic priorities OR initiatives" (narrative context)
- **Skip basic company info** (size, industry, revenue) - Already from Apollo

**Competitive Context:**
- `web_search` for: "[Company name] competitors OR landscape"
- Surface: where they stand, what gaps exist, differentiation opportunities
- **Combine with Apollo tech stack data** to identify competitor displacement opportunities

**Industry Context:**
- `web_search` for: "[Industry] trends OR challenges"
- Identify: macro themes to position your solution against

**Step 6: Synthesize Intelligence**
Compile findings from all sources into intelligence brief:
- **Relationship status** (new, warm, established, cold-reactivation) - From Gmail, Calendar, Conversations
- **Key decision-makers and their priorities** - From Apollo People Search + LinkedIn
- **Company profile & firmographics** - From Apollo Organization Enrichment
- **ICP fit & lead score** - From Apollo data vs. your ideal customer profile
- **Past interactions and any open loops** - From Gmail, Asana, Calendar
- **Competitive positioning opportunities** - From Apollo tech stack + web research
- **Strategic context for outreach** - From Apollo funding/growth data + recent news
- **Email verification status** - From Apollo (use only "verified" emails for cold outreach)

### Phase 2: Campaign Design

Based on intelligence gathered and campaign objective, design approach:

**For New Prospects (Cold Outreach):**
- 5-touch sequence over 3 weeks
- Email 1: Insight/value (no ask)
- Email 2: Case study/proof (soft ask)
- Email 3: Direct ask with urgency
- Email 4: Breakup/last chance
- Email 5: Different angle (if no response)

**For Warm Prospects (Following Up):**
- 3-touch sequence over 2 weeks
- Email 1: Reference past interaction + new value
- Email 2: Specific proposal/next step
- Email 3: Clear CTA with timeline

**For Stuck Deals (Re-Engagement):**
- 3-touch sequence over 10 days
- Email 1: Check-in acknowledging gap
- Email 2: New information/urgency trigger
- Email 3: Alternative path forward or close-out

**For Closed-Lost Reactivation:**
- 2-touch sequence over 1 week
- Email 1: Acknowledge past, share what's changed
- Email 2: Low-friction reconnection offer

### Phase 3: Content Generation

**Email Structure Template:**
```
Subject: [Clear value or curiosity without hype]

Hi [First Name],

[Hook: Insight, pattern, or connection that's relevant to them]

[Context: 2-3 sentences showing you understand their world]

[Value Prop: What you offer that solves their specific challenge]

[Social Proof: Brief case study or result with similar company]

[CTA: One clear next step]

[Signature]
```

**Personalization Variables to Populate:**
- `{{first_name}}` - From research or CRM
- `{{company_name}}` - Target company
- `{{recent_news}}` - Something specific you found
- `{{shared_connection}}` - If applicable from network
- `{{past_interaction}}` - Reference if relationship exists
- `{{industry_challenge}}` - Specific to their sector
- `{{competitor_insight}}` - Positioning against alternatives
- `{{case_study_company}}` - Similar customer
- `{{metric}}` - Specific result/outcome

**Subject Line A/B Test Options:**
Generate 3-5 variants:
- Insight-driven: "Your [Industry] competitors are doing this"
- Curiosity: "Quick question about [Company Name]"
- Value-first: "[Specific Result] for [Similar Company]"
- Pattern interrupt: "This is awkward..."
- Direct: "Partnership opportunity for [Company]"

### Phase 4: Deal Tracking & Pipeline Management

**Create or Update Deal in Asana:**
1. Use `asana_typeahead_search` to find "Sales Pipeline" project
2. Use `asana_create_task` with custom fields:
   - Deal Name: "[Company Name] - [Opportunity]"
   - Deal Stage: [Outreach, Discovery, Proposal, Negotiation, Closed-Won, Closed-Lost]
   - Deal Value: [Estimated ARR or project value]
   - Close Date: [Target close date]
   - Lead Source: [How they entered pipeline]
   - Assigned To: [Sales owner]
3. Use `asana_create_task_story` to log outreach sent
4. Set due date for next follow-up action

**Track Follow-Up Sequence:**
Create subtasks for each touch in sequence:
- Subtask 1: "Send Email 1: [Subject]" (due: today)
- Subtask 2: "Send Email 2: [Subject]" (due: +3 days)
- Subtask 3: "Send Email 3: [Subject]" (due: +7 days)
- Subtask 4: "Send Email 4: [Subject]" (due: +14 days)

**Set Reminders:**
Use `asana_add_task_followers` to notify sales owner and relevant stakeholders.

### Phase 5: Delivery & Tracking

**Standard Output Format:**
```
## Campaign: [Company Name] - [Opportunity Type]

**Intelligence Summary:**
- Relationship Status: [New/Warm/Cold Reactivation]
- Key Decision-Maker: [Name, Title]
- Strategic Context: [1-2 sentences on why this matters now]
- Competitive Positioning: [How to differentiate]

---

**Email Sequence (5 touches over 21 days)**

### Email 1: [Subject Line]
**Send: Day 0 (Immediately)**

[Full email body with personalization variables populated]

**A/B Test Subjects:**
- Option A: [Subject 1]
- Option B: [Subject 2]
- Recommended: [Option A/B with reasoning]

---

### Email 2: [Subject Line]
**Send: Day 3 (If no response to Email 1)**

[Full email body]

---

[Continue for all touches]

---

**Tracking Setup:**

✓ Deal created in Asana: [Link to task]
✓ Follow-up sequence scheduled: [Link to subtasks]
✓ Sales owner notified: [Name]
✓ Next action due: [Date]

**Metrics to Monitor:**
- Email open rate (track via email client)
- Response rate
- Meeting booking rate
- Days to response
- Deal velocity (time in each stage)

**Success Criteria:**
- Primary: Book discovery meeting
- Secondary: Get response/engagement
- Tertiary: Advance to proposal stage

---

**Optimization Notes:**
[Any specific recommendations based on prospect profile or past campaign performance]
```

## Email Template Library

For complete template library with variations, see [REFERENCE.md](references/REFERENCE.md).

### Quick Reference Templates

**Cold Outreach - Insight-Led:**
```
Subject: [Insight about their industry/company]

Hi {{first_name}},

I've been following {{company_name}}'s work in {{industry}} and noticed [specific observation about their strategy/recent move].

Here's something you might find interesting: We've helped {{similar_company}} achieve {{specific_metric}} by addressing [specific challenge that likely applies to target too].

Not sure if this is relevant for {{company_name}}, but I figured it was worth sharing.

Would 15 minutes next week make sense to explore if there's a fit?

Best,
[Name]
```

**Follow-Up - Referencing Past Interaction:**
```
Subject: Following up on [specific topic from last interaction]

Hi {{first_name}},

Quick follow-up on our conversation about {{past_topic}}.

You mentioned {{specific_challenge_they_raised}}. Since we last talked, we've [relevant development/new capability/case study] that directly addresses this.

**What's new:** [2-3 sentence explanation of value]

**Next step:** Let's reconnect for 15 minutes to see if this changes the equation for {{company_name}}.

Available [day/time options]?

Best,
[Name]
```

**Proposal Introduction:**
```
Subject: Partnership Proposal for {{company_name}}

Hi {{first_name}},

Following up on our discussion, I've put together a proposal outlining how we could partner on {{specific_opportunity}}.

**What this includes:**
- [Deliverable 1]
- [Deliverable 2]
- [Deliverable 3]

**Timeline:** [Specific phases]
**Investment:** [Clear pricing]
**Expected Outcome:** [Specific results]

Attached is the full proposal. Would {{day}} or {{day}} work for a call to walk through it?

Best,
[Name]
```

**Stuck Deal Re-Engagement:**
```
Subject: Checking in on {{company_name}} partnership

Hi {{first_name}},

It's been {{weeks_since_last_contact}} weeks since we last connected about {{opportunity}}.

I know priorities shift, so I wanted to check in: Is this still on your radar, or should I follow up at a different time?

If timing's just off right now, no problem. I can circle back in {{suggested_timeframe}}.

Let me know what makes sense.

Best,
[Name]
```

**Breakup Email (Final Touch):**
```
Subject: Last email (I promise)

Hi {{first_name}},

I've reached out a few times about {{opportunity}} but haven't heard back.

I'll take that as a sign this isn't a priority right now, which is totally fine.

I'll stop filling your inbox. But if circumstances change, you know where to find me.

Best,
[Name]
```

## Deal Pipeline Management

### Custom Fields in Asana

Set up "Sales Pipeline" project with these custom fields:

**Deal Stage** (Dropdown):
- Outreach (initial contact sent)
- Discovery (first meeting scheduled/completed)
- Proposal (proposal sent)
- Negotiation (discussing terms)
- Closed-Won (deal signed)
- Closed-Lost (deal lost)

**Deal Value** (Number):
- Estimated ARR or project value

**Close Date** (Date):
- Target close date

**Lead Source** (Dropdown):
- Inbound
- Outbound Cold
- Referral
- Partnership
- Event
- Content Marketing

**Lead Score** (Dropdown):
- Hot (ready to buy)
- Warm (interested, needs nurturing)
- Cold (not responsive)

**Next Action** (Text):
- What's the next step in this deal?

### Pipeline Health Checks

**Weekly Pipeline Review:**
Use `asana_search_tasks` with filters:
- `project_id`: Sales Pipeline project
- `custom_fields`: Deal Stage = "Discovery" OR "Proposal" OR "Negotiation"
- `assignee`: "me"

**Identify Stuck Deals:**
- Any deal in "Discovery" stage > 14 days
- Any deal in "Proposal" stage > 21 days
- Any deal in "Negotiation" stage > 30 days
- Trigger re-engagement sequence

**Forecast Pipeline:**
Calculate weighted pipeline value:
- Outreach: Deal Value × 10%
- Discovery: Deal Value × 25%
- Proposal: Deal Value × 50%
- Negotiation: Deal Value × 75%
- Closed-Won: Deal Value × 100%

Sum weighted values to get pipeline forecast.

## Competitive Intelligence Protocol

### Prospect Company Research

**Step 1: Company Overview**
`web_search`: "[Company Name] overview OR about"
Capture: Size, revenue, locations, business model, key products

**Step 2: Recent Developments**
`web_search`: "[Company Name] news OR announcements recent"
Capture: Funding, product launches, partnerships, leadership changes

**Step 3: Strategic Priorities**
`web_search`: "[Company Name] strategic priorities OR initiatives OR roadmap"
Capture: What they're focusing on, where they're investing

**Step 4: Decision-Makers**
`web_search`: "[Company Name] leadership team OR executives"
`web_search`: "[Decision Maker Name] [Company Name] LinkedIn"
Capture: Names, titles, backgrounds, priorities

**Step 5: Competitor Landscape**
`web_search`: "[Company Name] competitors OR alternatives"
Capture: Who they're evaluating, what they're using now

**Step 6: Industry Context**
`web_search`: "[Industry] trends OR challenges"
Capture: Macro forces, regulatory changes, market shifts

### Differentiation Positioning

Based on research, identify:
- **Their Pain Points**: What challenges are they facing?
- **Competitor Weaknesses**: What do alternatives not do well?
- **Your Unique Value**: What do you offer that's differentiated?
- **Proof Points**: Case studies with similar companies
- **Urgency Triggers**: Why act now vs. later?

Incorporate these into outreach messaging.

## Performance Analytics

### Key Metrics to Track

**Email Performance:**
- Open Rate: % of emails opened
- Response Rate: % of emails that get replies
- Meeting Booking Rate: % that convert to meetings
- Time to Response: Average days from send to reply

**Pipeline Metrics:**
- New Deals Added: # of new opportunities per week
- Deal Velocity: Average days in each stage
- Win Rate: % of deals that close
- Average Deal Size: Mean deal value
- Pipeline Coverage: Total pipeline value / quota

**Sequence Performance:**
- Which email in sequence gets most responses?
- Which subject lines have highest open rates?
- Which CTAs convert best?
- Which personalization variables correlate with response?

### Data Collection

**From Gmail:**
Use `search_gmail_messages` to track sent vs. replied:
- Query: `from:me subject:[Campaign Name]`
- Count total sent
- Count with replies
- Calculate response rate

**From Asana:**
Use `asana_sear