Sales AI Skill

Prospecting Playbook

Build and execute prospecting playbooks for outbound sales including target account identification, prospect research, multi-channel outreach, cadence design, and prospect engagement tracking. Use when developing prospecting strategies, designing outreach s...

Prospecting Playbook & Targeting

Systematic approach to identifying, researching, and engaging target accounts and prospects for outbound sales.

Workflow

1. Ideal Customer Profile & Targeting

ICP definition and refinement:

Firmographic criteria: industry, company size, revenue, geography
Technographic criteria: current technology stack, integration requirements
Behavioral criteria: growth signals, funding events, hiring patterns
Pain point alignment: challenges your solution addresses
Buying timeline and trigger events

Target account list building:

Strategic account identification (top 100-500 accounts)
Vertical and horizontal list building
Prospect database enrichment and cleansing
Account tiering (tier 1: strategic, tier 2: high potential, tier 3: standard)
Continuous list refresh and expansion

Buying committee mapping:

Economic buyer identification (budget authority)
Champion/advocate identification (internal sponsor)
Technical evaluator identification
End user and influence mapping
Blocker/risk taker identification

2. Prospect Research & Intelligence

Account-level research:

Company overview: business model, strategy, competitive position
Financial health: revenue, growth, funding, profitability
Recent events: earnings calls, press releases, leadership changes
Technology stack: current vendors, upgrade cycles, gaps
Strategic initiatives: digital transformation, expansion, consolidation

Contact-level research:

Professional background and career trajectory
Current role and responsibilities
Personal interests and background (for personalization)
Social media presence and content
Pain points and priorities for role

Intelligence synthesis and personalization:

Account briefing document creation
Personalized value hypothesis development
Relevant case study and reference identification
Conversation starter development
Multi-threading opportunity identification

3. Outreach Cadence & Multi-Channel Strategy

Cadence design:

Touch count and sequencing (12-20 touches over 4-6 weeks)
Channel mix: email, phone, LinkedIn, video, direct mail, events
Timing and spacing between touches
Escalation logic (increase intensity if no response)
Break/stop criteria (explicit not interested, voicemail after X attempts)

Email outreach optimization:

Subject line strategy (curiosity, relevance, personalization, brevity)
Email body structure: hook, relevance, value, CTA
Personalization tokens and data-driven customization
Send time optimization by prospect profile
Follow-up sequencing and variation

Phone and social outreach:

Cold call script framework (not rigid script, conversation guide)
Voicemail strategy (leave value, not just "call me back")
LinkedIn engagement strategy (connection, content share, InMail)
Social selling best practices
Cross-channel message alignment

4. Engagement & Qualification

Response handling:

Positive response: next step scheduling and qualification
"Not interested": objection handling and re-engagement path
"Send information": value delivery and follow-up scheduling
"Too busy": rescheduling and alternate contact suggestion
Gatekeeper navigation: receptionist, EA, assistant engagement

Discovery and qualification:

Transition from outreach to discovery
MEDDPICC/BANT qualification criteria validation
Pain and impact exploration
Decision process and timeline understanding
Next step commitment and scheduling

Multi-threading strategy:

Additional stakeholder identification
Referral request within account
Parallel outreach to multiple contacts
Relationship mapping and influence network
Risk mitigation through multiple relationships

5. Prospecting Analytics & Optimization

Performance measurement:

Outreach volume metrics (emails sent, calls made, connections)
Response rate by channel and cadence
Meeting booking rate
SQL conversion rate from prospecting
Revenue attribution from outbound

Optimization experiments:

A/B testing: subject lines, email body, CTA, send time
Channel effectiveness testing
Message testing by ICP segment
Cadence length and intensity testing
Personalization depth testing

Continuous improvement:

Top performer analysis and technique extraction
Prospecting playbook quarterly review
ICP refinement based on conversion data
Message refinement based on response data
Tool and technology evaluation

Templates & Frameworks

Prospecting Cadence Template

OUTBOUND PROSPECTING CADENCE — 6-Week, 18-Touch
=================================================

WEEK 1: Introduction & Awareness
  Day 1: Email 1 — Personalized intro, value proposition
  Day 1: LinkedIn connection request — no note
  Day 2: Call 1 — Voicemail if no answer
  Day 3: Email 2 — Case study relevant to prospect's industry
  Day 3: LinkedIn engagement — comment on prospect's post

WEEK 2: Value & Engagement
  Day 4: Call 2 — Different time of day
  Day 5: Email 3 — Personalized video (2 min max)
  Day 6: LinkedIn InMail — Reference mutual connection or event
  Day 8: Direct mail — relevant industry report or book

WEEK 3: Social Proof & Urgency
  Day 9: Email 4 — Customer testimonial + ROI data
  Day 10: Call 3 — Final phone attempt
  Day 11: Email 5 — Industry trend insight + relevance
  Day 12: LinkedIn content share — value-driven (not salesy)

WEEK 4-5: Persistence & Break Attempt
  Day 14: Email 6 — "Is this a priority?" break-up email
  Day 16: Call 4 — Voicemail with alternative suggestion
  Day 18: Email 7 — Last attempt, value summary
  Day 20: LinkedIn check-in — casual engagement

WEEK 6: Final Attempt & Nurture Handoff
  Day 22: Email 8 — Final value email, nurture opt-in offer
  Day 24: If no response → add to nurture program
  Day 24: If positive response → schedule discovery call

BREAK CRITERIA:
  Explicit "not interested" → remove from active cadence, add to nurture
  "Contact in X months" → calendar reminder, re-engage at specified time
  "Wrong person" → request redirect to correct contact
  Gatekeeper blocks all channels → pause 30 days, try alternate approach

RESPONSE HANDLING:
  Positive → Schedule discovery within 48 hours, send calendar link
  "Send info" → Send targeted one-pager, schedule follow-up for 1 week later
  "Too expensive" → Value reinforcement, request discovery to quantify ROI
  "Competitor" → Competitive differentiation, request comparison meeting

Account Briefing Document

ACCOUNT BRIEFING — [Account Name]
==================================

COMPANY OVERVIEW:
  Industry: [sector] | Size: [employees] | Revenue: [$amount]
  Headquarters: [location] | Public/Private: [status]
  Business model: [description]
  Strategic priorities: [from earnings call/press releases]

TECHNOLOGY STACK:
  Current [product category]: [vendor, version, contract end]
  Related technologies: [list]
  Technology gaps/opportunities: [identified gaps]
  Recent tech investments: [from press, job postings, filings]

KEY CONTACTS:
  Economic buyer: [Name, Title, LinkedIn, email, phone]
  Champion: [Name, Title, relationship level]
  Technical evaluator: [Name, Title]
  End users: [Names, Titles]
  Additional stakeholders: [Names, Titles]

PAIN HYPOTHESIS:
  Primary pain: [based on research, industry trends, job postings]
  Secondary pain: [additional challenges]
  Business impact: [quantified if possible]
  Current workaround: [what they're using/doing now]

VALUE PROPOSITION:
  Relevant use case: [specific to their situation]
  ROI estimate: [based on similar customer results]
  Key differentiators: [vs their current solution/competitors]
  Relevant case study: [similar company/industry]

CONVERSATION STARTERS:
  "I saw [recent news/event] — how is that impacting [relevant area]?"
  "Many [industry] companies are seeing [trend]. Are you experiencing that?"
  "Your [initiative] caught my attention — we helped [similar company] achieve [result]"

COMPETITIVE LANDSCAPE:
  Incumbent vendor: [name] — [strengths, weaknesses, contract status]
  Alternatives evaluated: [if known]
  Switching factors: [triggers, timing, budget cycle]

NEXT STEPS:
  [ ] Begin cadence (recommended start date)
  [ ] Prepare personalized email sequence
  [ ] Schedule account team briefing
  [ ] Prepare discovery call agenda

Integration Points

CRM platforms (Salesforce, HubSpot): Account and contact management
Prospecting tools (ZoomInfo, LinkedIn Sales Navigator, Lusha): Contact discovery
Intent data platforms (6sense, Demandbase, G2): Buying signals
Email outreach platforms (Outreach, Salesloft, Apollo): Cadence execution
Sales engagement platforms: Activity tracking and coaching
Social selling (LinkedIn, Twitter): Social outreach
Account intelligence (Clearbit, Owler, Crunchbase): Company data
Conversation intelligence (Gong, Chorus): Call analysis and coaching

Edge Cases

No visible pain or trigger event: Create awareness through educational outreach; industry trend insight sharing; problem-space messaging; nurture until trigger occurs
Long sales cycles (6+ months): Extended cadence with nurture integration; periodic re-engagement; relationship building before direct ask; multi-touchpoint presence
Highly competitive accounts: Competitive intelligence deep dive; unique value differentiation; champion development; executive sponsorship alignment
Regulated industries with strict procurement: Procurement process understanding early; compliance value articulation; security review preparation; extended stakeholder mapping
Global accounts with distributed decision-making: Multi-region stakeholder mapping; local champion development; regional customization; time-zone-aware outreach

Output

Prospecting Performance Dashboard

PROSPECTING PERFORMANCE — April 2025
======================================

ACTIVITY METRICS:
  Total prospects in active cadences: 847
  Emails sent: 6,234 (avg 7.4/prospect)
  Calls made: 3,102 (avg 3.7/prospect)
  LinkedIn connections: 1,203
  Total touches: 14,539

RESPONSE METRICS:
  Overall response rate: 12.4% ✓
  Email response rate: 8.7%
  Phone response rate: 21.3%
  LinkedIn response rate: 6.2%
  Positive response rate: 6.8%

CONVERSION METRICS:
  Meetings booked: 127 (15.0% of responders)
  Discovery calls completed: 108
  SQLs generated: 47 (5.5% of prospects)
  Opportunities created: 23
  Pipeline generated: $1.87M

CADENCE EFFECTIVENESS:
  Avg touches before response: 4.2
  Best response touch: Email 3 (personalized video) — 14.3% response
  Best response day: Tuesday — 15.2% response
  Best response time: 10:00-11:00 AM — 13.8% response
  Cadence completion rate: 78%

TOP PERFORMERS:
  Rep #1: 23 SQLs, 34% response rate
  Rep #2: 18 SQLs, 28% response rate
  Rep #3: 15 SQLs, 26% response rate
  Team avg: 9.4 SQLs, 12.4% response rate

ICP CONVERSION BY SEGMENT:
  Tier 1 (strategic): 8.2% SQL rate (higher effort, higher value)
  Tier 2 (high potential): 6.1% SQL rate
  Tier 3 (standard): 4.3% SQL rate
  Non-ICP (control): 2.1% SQL rate (validates ICP effectiveness)

A/B TEST RESULTS:
  Test 1: Video vs text email — Video won (+34% response)
  Test 2: Morning vs afternoon — Morning won (+18% response)
  Test 3: Personalization depth — Moderate won (vs light or heavy)
  Active tests: 3 more running

Trigger Phrases

"prospecting", "outbound", "target account", "cold outreach", "prospecting cadence", "ICP targeting", "account research", "prospect list", "sales development", "SDR playbook", "multi-channel outreach", "account mapping", "buying committee", "discovery call", "qualification"