Sales AI Skill

Sales Prospecting Outreach

Execute outbound sales prospecting including lead research, personalized outreach sequences, multi-channel campaigns, objection handling, and prospect engagement tracking. Use when building prospect lists, crafting outreach sequences, running cold campaigns...

Sales Prospecting & Outreach

Execute outbound sales prospecting including lead research, personalized outreach sequences, multi-channel campaigns, and prospect engagement tracking.

Workflow

1. Prospect Research & Targeting

PROSPECT RESEARCH FRAMEWORK
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Ideal Customer Profile (ICP):
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  Firmographics:
    → Industry: SaaS, FinTech, Healthcare Tech
    → Company size: 200-2,000 employees
    → Revenue: $20M - $200M
    → Geography: North America, Western Europe
    → Tech stack: Uses [competitive product], AWS/Azure
    → Growth stage: Scaling (Series B+)

  Decision Makers:
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  Role                  Title Examples            Pain Points          Influence
  ─────────────────────────────────────────────────────────────────────────────────────
  Economic Buyer        CEO, CFO, VP             Budget, ROI           HIGH (approves)
  Champion              Director, Manager        Pain point, solution  HIGH (advocates)
  Technical Buyer       CTO, Architect           Technical fit, security MEDIUM (evaluates)
  End Users             Team members             Usability, workflow   LOW (influences)

PROSPECTING DATA SOURCES:
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  Source                Data Available            Accuracy    Cost       Update Frequency
  ────────────────────────────────────────────────────────────────────────────────────────
  LinkedIn Sales Nav    Contact info, triggers    90%         $99/mo     Real-time
  ZoomInfo              Email, phone, org chart   85%         $15K/yr    Monthly
  Apollo                Email, phone, sequences   80%         $9K/yr     Monthly
  Clearbit              Tech stack, firmographics 85%         $5K/yr     Weekly
  Hunter                Email find/verify         80%         $35/mo     On-demand
  Crunchbase            Funding, M&A, growth      90%         $2K/yr     Daily
  BuiltWith             Tech stack                95%         $5K/yr     Daily

PROSPECT LIST BUILDING:
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  1. Define ICP criteria (firmographics, technographics)
  2. Pull list from data source (LinkedIn, ZoomInfo, Apollo)
  3. Enrich with additional data (Crunchbase, BuiltWith)
  4. Verify contact info (email, phone)
  5. Segment by priority (fit, timing, budget)
  6. Assign to reps (territory, industry, round-robin)
  7. Load into CRM (Salesforce, HubSpot, Pipedrive)

2. Outreach Sequence Design

MULTI-CHANNEL OUTREACH SEQUENCE (14 days, 8 touches)
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Day 1: Cold Email #1 — Value-First Introduction
  → Subject: "Quick question about [company] [challenge]"
  → Body: Personalized opener → Pain point → Social proof → Soft CTA
  → Length: 100-150 words
  → CTA: Reply with "yes" or schedule 15 min

Day 1: LinkedIn Connection Request
  → Note: "Hi [Name], noticed your work at [company]. Would love to connect"
  → No pitch in connection request

Day 3: Cold Email #2 — Social Proof
  → Subject: "How [similar company] solved [problem]"
  → Body: Case study reference → Results achieved → Relevance to prospect → CTA
  → CTA: "Interested in seeing how?"

Day 5: LinkedIn InMail / Message (if connected)
  → Content: Share relevant article or insight
  → CTA: "Thoughts on this approach?"

Day 7: Cold Call #1
  → Script: Introduction → Reason for calling → Value proposition → Question → Next step
  → Voicemail: 30 seconds, one ask, callback number

Day 9: Cold Email #3 — Direct Approach
  → Subject: "Worth exploring?"
  → Body: Direct value prop → Specific benefit → Social proof → CTA
  → CTA: "Open to a 15-min call this week?"

Day 11: Cold Call #2
  → Different angle (new insight, recent trigger)
  → Voicemail: Different message from first

Day 14: Breakup Email
  → Subject: "Should I close your file?"
  → Body: Polite, no pressure, leave door open
  → CTA: "If timing isn't right, no worries — just let me know"

SEQUENCE VARIATIONS:
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  By Persona:
    → Executive: Focus on ROI, strategy, competitive advantage
    → Technical: Focus on integration, security, architecture
    → Manager: Focus on team efficiency, workflow, reporting

  By Trigger:
    → Funding announcement: Congratulate + relevant use case
    → Hiring spree: Growing team → need for tools
    → New product launch: Complementary solution
    → Competitor switch: Migration story + benefits

3. Email Templates

COLD EMAIL #1 — VALUE-FIRST (100-150 words)
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Subject: Quick question about [company] [challenge]

Hi [First Name],

I noticed [specific observation about company — recent news, product launch,
LinkedIn post, hiring trend].

We recently helped [similar company] [achieve specific result — reduce X by Y%,
increase Z by $amount] in [timeframe].

Given [relevant context], I thought there might be a fit.

Would you be open to a brief 15-minute call this week to explore? If not, no
worries — just reply and I'll keep you in mind for the future.

Best,
[Your Name]
[Title] | [Company]

COLD EMAIL #2 — SOCIAL PROOF (100-150 words)
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Subject: How [similar company] solved [problem]

Hi [First Name],

[Similar company] was struggling with [specific pain point]. Sound familiar?

They implemented [solution] and saw:
  → [Result 1: metric improved by X%]
  → [Result 2: time saved by Y hours/week]
  → [Result 3: revenue impact of $Z]

I think [Prospect's company] could see similar results.

Can I share a quick 5-minute walkthrough of how it works?

Best,
[Your Name]

BREAKUP EMAIL (50-75 words)
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Subject: Should I close your file?

Hi [First Name],

I've reached out a few times about [topic], but I don't want to be a nuisance.

Should I close your file for now? If [problem] becomes a priority down the road,
feel free to reach out.

Best,
[Your Name]

NOTE: Breakup emails have 2-3x response rate of regular emails

4. Cold Calling Framework

COLD CALL SCRIPT FRAMEWORK
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Opening (10 seconds):
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  "Hi [Name], this is [Your Name] from [Company]. I know I'm catching you
  out of the blue — do you have 30 seconds?"

  If yes → Continue
  If no → "No problem, when's a better time?" → Schedule callback

Reason for Calling (20 seconds):
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  "The reason I'm calling is we help companies like [Prospect's Company]
  solve [specific pain point]. We recently helped [Similar Company] achieve
  [specific result]."

Discovery Question (15 seconds):
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  "How are you currently handling [related process]?"
  OR
  "Are you currently looking into solutions for [pain point]?"

Next Step (15 seconds):
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  "Based on what you've shared, I think there's a strong fit. Can I schedule
  a 15-minute call with our solutions team this [day]?"

  → If yes → Schedule on calendar
  → If no → "No worries — mind if I send a quick email with more info?"

VOICEMAIL SCRIPT (30 seconds):
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  "Hi [Name], this is [Your Name] from [Company]. We help companies like
  yours [specific benefit]. I'd love to share how [Similar Company] achieved
  [result]. Call me at [number] or reply to my email. Thanks!"

OBJECTION HANDLING:
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  Objection: "Not interested"
  Response: "I understand. Is it timing, or doesn't this align with your priorities?"

  Objection: "We're happy with current solution"
  Response: "That's great. What's working well? Many of our customers came from [competitor] because of [differentiator]."

  Objection: "Send me info"
  Response: "Happy to. What specifically are you looking for? I'll make sure it's relevant."

  Objection: "Too expensive"
  Response: "Understood. What's your budget range? We have flexible options."

5. Prospecting Metrics & Tracking

PROSPECTING METRICS DASHBOARD
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Activity Metrics (Weekly per Rep):
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Metric              Target        Current      Status
───────────────────────────────────────────────────────────────
Cold emails sent    150           165          ✓ Above target
Cold calls made     80            72           Below target
LinkedIn messages   40            45           ✓ Above target
Connections sent    30            28           Near target
Follow-ups          100           95           Near target

Outcome Metrics (Monthly):
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Metric              Target        Current      Status
───────────────────────────────────────────────────────────────
Email open rate     ≥ 45%         52%          ✓ Good
Email reply rate    ≥ 5%          6.8%         ✓ Good
Calls connected     ≥ 25%         28%          ✓ Good
Meetings booked     20            24           ✓ Above target
SQLs generated      8             10           ✓ Above target
Revenue influenced  $50K          $68K         ✓ Above target

CONVERSION FUNNEL:
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  Prospects contacted: 500
    → Engaged (reply/call connected): 125 (25%)
      → Qualified: 50 (10%)
        → Meeting booked: 24 (4.8%)
          → Demo completed: 18 (3.6%)
            → Proposal sent: 12 (2.4%)
              → Closed-won: 5 (1.0%)

  Overall conversion: 500 → 5 (1.0%)
  Target conversion: 1.5% (improvement needed)
  Average deal size: $25,000
  Revenue per prospect: $500

Edge Cases

Integration Points

Output

Prospecting Status

PROSPECTING — Q4 2024
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Prospects contacted: 1,850
Meetings booked: 89 (4.8% conversion)
SQLs: 34 (1.8% conversion)
Revenue influenced: $256,000
Avg reply rate: 6.8% (target: ≥5%) ✓
Top channel: Cold email (62% of meetings)
Best performing sequence: 14-day, 8-touch
Next priority: Improve cold call connect rate (28% → 35%)