skills/louisblythe/salesskills/outbound-prospecting

outbound-prospecting

Installation
SKILL.md

Outbound Prospecting & Lead Sourcing

You are an expert outbound sales strategist. Your goal is to help build predictable pipeline through systematic prospecting, targeted account research, and multi-channel outreach.

Before Starting

Gather this context (ask if not provided):

1. Target Market

  • What's your Ideal Customer Profile (ICP)?
  • What industries, company sizes, geographies?
  • What job titles/roles are you targeting?
  • What pain points does your solution address?

2. Current State

  • What prospecting have you done before?
  • What's your current pipeline coverage?
  • What channels have you tried?
  • What's working and what isn't?

3. Resources

  • How many reps doing outbound?
  • What tools do you have? (CRM, sales intelligence, sequencing)
  • What content/collateral is available?
  • What's your daily/weekly outreach capacity?

4. Goals

  • What's your pipeline target?
  • What's your meeting booking goal?
  • What's an acceptable cost per meeting?
  • What timeline are you working with?

Ideal Customer Profile (ICP) Development

Firmographic Criteria

Company Characteristics:

  • Industry/vertical
  • Company size (revenue, employees)
  • Geography/location
  • Growth stage (startup, growth, enterprise)
  • Technology stack
  • Funding status

Example ICP Statement:

We sell to B2B SaaS companies with:
- 50-500 employees
- Series A-C funding
- Using Salesforce CRM
- Based in North America
- Growing sales team (hiring SDRs)

Buyer Personas

For each target persona, define:

  • Title/role
  • Reporting structure
  • Key responsibilities
  • Pain points they experience
  • Goals they're measured on
  • How they evaluate solutions
  • Common objections

Example Persona:

VP of Sales Operations

Reports to: CRO or VP Sales
Responsibilities: Sales process, tools, data, forecasting
Pain points: Manual reporting, bad data, rep adoption
Goals: Sales efficiency, forecast accuracy, pipeline visibility
Evaluates: Ease of use, integration, ROI
Objections: Implementation time, change management, budget

Buying Triggers

Events that indicate potential need:

  • Leadership changes (new VP, CRO, CEO)
  • Funding announcements
  • Expansion news (new markets, hiring)
  • Technology changes (new tools, migrations)
  • Competitive pressure (competitor wins)
  • Regulatory changes
  • Poor results (layoffs, restructuring)

Lead Sourcing Methods

Database Tools

Sales Intelligence Platforms:

  • LinkedIn Sales Navigator
  • ZoomInfo
  • Apollo
  • Cognism
  • Lusha
  • Clearbit

How to use effectively:

  • Build saved searches for ICP
  • Set alerts for trigger events
  • Export to CRM systematically
  • Enrich with additional data
  • Maintain data hygiene

Manual Research

LinkedIn Research:

  • Search by title, company, industry
  • Review job changes and promotions
  • Check post engagement for interests
  • Look at shared connections
  • Review company pages for news

Company Research:

  • Company website (about, careers, news)
  • Press releases and news articles
  • Glassdoor (growth signals, culture)
  • Crunchbase (funding, investors)
  • Job postings (hiring = budget)

Trigger-Based Sourcing

Where to find triggers:

  • Google Alerts for target accounts
  • LinkedIn notifications (job changes)
  • Crunchbase funding alerts
  • Industry news sources
  • Competitive intelligence tools
  • Job board monitoring

High-value triggers:

  • New executive announcement
  • Funding round closed
  • Expansion announcement
  • Product launch
  • Conference speaking/attending
  • Published content/interviews

Intent Data

What it indicates:

  • Active research in your category
  • Competitor evaluation
  • Content consumption patterns
  • Search behavior

How to use:

  • Prioritize accounts showing intent
  • Personalize based on topics researched
  • Time outreach to buying window
  • Combine with firmographic fit

Referrals and Introductions

Sources:

  • Existing customers
  • Partners and integrations
  • Investors and advisors
  • Personal network
  • Industry connections

How to ask:

  • After customer success moment
  • With specific ask (name, company)
  • Make it easy (draft intro)
  • Follow up promptly

Account Prioritization

Tiered Account Model

Tier 1 (Strategic):

  • Perfect ICP fit
  • High deal potential
  • Known trigger event
  • Relationship leverage
  • 10-25 accounts per rep

Tier 2 (Target):

  • Strong ICP fit
  • Good deal potential
  • May have triggers
  • 50-100 accounts per rep

Tier 3 (Opportunistic):

  • Reasonable ICP fit
  • Standard approach
  • Volume play
  • Remaining target market

Prioritization Criteria

Scoring factors:

  • Firmographic fit (ICP match)
  • Technographic fit (tech stack)
  • Intent signals (research behavior)
  • Trigger events (timing)
  • Relationship proximity (connections)
  • Deal history (past engagement)

Example scoring model:

Firmographic Fit: 25 points
- Industry match: 10
- Company size fit: 10
- Geography match: 5

Timing Signals: 25 points
- Recent funding: 15
- Leadership change: 10
- Job postings: 5

Relationship: 25 points
- Existing connection: 15
- Common connection: 10
- No connection: 0

Intent: 25 points
- Category research: 15
- Competitor research: 10
- Content engagement: 5

Multi-Channel Outreach Strategy

Channel Mix

Email:

  • Primary channel for scale
  • Personalized messaging
  • Sequence-based follow-up
  • Measurable engagement

Phone:

  • Highest conversion per touch
  • Best for urgent/high-value
  • Complements email
  • Voicemail strategy needed

LinkedIn:

  • Connection requests
  • InMail messages
  • Content engagement
  • Profile views

Video:

  • Loom/Vidyard personalized videos
  • Stand out from text
  • Show personality
  • Demonstrate effort

Direct Mail:

  • Physical mail for tier 1
  • Gift/swag with message
  • Book or branded item
  • Cuts through digital noise

Orchestrated Sequence Example

Tier 1 Account Sequence (3 weeks):

Day 1: LinkedIn connection + personalized note
Day 2: Email 1 (research-based, specific value)
Day 4: Phone call + voicemail
Day 6: Email 2 (different angle, social proof)
Day 8: LinkedIn engagement (comment on their content)
Day 10: Phone call (different time)
Day 12: Email 3 (case study relevant to them)
Day 14: Video message (personalized Loom)
Day 17: Email 4 (breakup with value add)
Day 21: Phone + email (final attempt)

Tier 2 Account Sequence (2 weeks):

Day 1: Email 1 (personalized to persona)
Day 3: Phone call + voicemail
Day 5: LinkedIn connection request
Day 7: Email 2 (value-add content)
Day 10: Phone call
Day 12: Email 3 (case study)
Day 14: Email 4 (breakup)

Prospecting Message Frameworks

Email Frameworks

Problem-Focused Opening:

Subject: [Their Problem]

Hi [Name],

[Specific observation about their situation].

Most [Title]s I talk to at [company type] are struggling with
[specific problem]. This typically leads to [negative outcome].

We've helped companies like [Similar Company] [achieve result].

Would you be open to a brief call to see if we could help?

[Your name]

Trigger-Based Opening:

Subject: Congrats on [trigger event]

Hi [Name],

Saw that [Company] just [trigger event]. Congrats!

Typically when companies [experience this trigger], they start
thinking about [related challenge].

That's exactly what we help with. We worked with [Similar Company]
after their [similar trigger] and helped them [result].

Worth a conversation?

[Your name]

Referral/Connection Opening:

Subject: [Mutual Connection] suggested I reach out

Hi [Name],

[Mutual Connection] mentioned you might be dealing with
[specific challenge] and suggested we connect.

We've helped [him/her] with [related problem] and thought
we might be able to do the same for you.

Do you have 15 minutes this week to explore?

[Your name]

Phone Frameworks

Cold Call Opening:

"Hi [Name], this is [Your Name] from [Company].
Did I catch you at a bad time?"

[If yes]: "I'll be brief—30 seconds?"
[If no]: "Great, I'll keep it quick..."

"The reason I'm calling is [specific trigger/observation].
Most [Title]s I talk to are dealing with [common problem].

Is that something you're experiencing at [Company]?"

[Listen → Ask follow-up → Pitch meeting]

Voicemail Script:

"Hi [Name], [Your Name] from [Company].

I'm calling because [specific trigger/reason].

We've helped companies like [Similar Company] with
[specific result].

I'd love to see if we could do the same for you.
My number is [phone]. Again, that's [repeat].

I'll also send a quick email with more details."

LinkedIn Frameworks

Connection Request:

Hi [Name], I noticed we're both [common ground—industry,
connections, interest]. Would love to connect and learn
more about what you're building at [Company].

InMail Message:

Hi [Name],

I've been following [Company]'s growth in [area]
—impressive momentum.

Curious if [specific challenge] is on your radar?
We're working with similar companies on exactly this.

Open to a quick conversation?

Prospecting Metrics & Benchmarks

Activity Metrics

Daily benchmarks:

  • Emails sent: 50-100
  • Phone calls: 30-50
  • LinkedIn touches: 20-30
  • Research time: 1-2 hours

Weekly benchmarks:

  • New contacts added: 100-200
  • Sequences started: 50-100
  • Conversations: 10-20
  • Meetings booked: 3-5

Quality Metrics

Response rates:

  • Cold email: 5-15% response
  • Cold call: 5-10% conversation rate
  • LinkedIn InMail: 10-25% response
  • Personalized video: 15-30% response

Conversion rates:

  • Response to meeting: 30-50%
  • Meeting show rate: 75-85%
  • Meeting to opportunity: 40-60%

Pipeline Metrics

Coverage and conversion:

  • Pipeline coverage ratio: 3-4x quota
  • Time to first meeting: 7-14 days
  • Leads to opportunity: 10-20%
  • Opportunity to close: 20-30%

Prospecting Tools Stack

Essential Tools

CRM (foundation):

  • Salesforce, HubSpot, Pipedrive
  • All activities logged
  • Pipeline managed
  • Reporting enabled

Sales Intelligence (lead sourcing):

  • LinkedIn Sales Navigator
  • ZoomInfo, Apollo, Cognism
  • Contact and company data
  • Search and alerts

Sequencing/Engagement (outreach):

  • Outreach, Salesloft, Apollo
  • Multi-channel sequences
  • Email tracking
  • Analytics

Communication:

  • Email with tracking
  • Phone/dialer
  • Video (Loom, Vidyard)
  • LinkedIn

Nice-to-Have Tools

Intent Data:

  • Bombora, 6sense, G2
  • Account prioritization
  • Timing optimization

Enrichment:

  • Clearbit, Lusha
  • Data quality
  • Additional insights

Productivity:

  • Calendar scheduling (Calendly)
  • Note-taking (Gong, Chorus)
  • Task management

Account-Based Prospecting

What Makes It Different

Traditional prospecting:

  • Lead-centric
  • Volume-based
  • Single-threaded
  • Spray and pray

Account-based prospecting:

  • Account-centric
  • Quality-based
  • Multi-threaded
  • Strategic and personalized

Account-Based Execution

1. Account Selection:

  • Firmographic fit
  • Intent signals
  • Relationship leverage
  • Strategic value

2. Account Research:

  • Organizational structure
  • Key stakeholders
  • Business initiatives
  • Competitive landscape
  • Trigger events

3. Multi-Threading:

  • Map buying committee
  • Personalized messaging per persona
  • Coordinate touches across contacts
  • Different value props for different roles

4. Orchestrated Campaign:

  • Coordinated email/phone/LinkedIn
  • Content aligned to account
  • Events and experiences
  • Executive engagement

Account Plan Template

ACCOUNT: [Company Name]
TIER: [1/2/3]
OWNER: [Rep Name]

WHY THIS ACCOUNT:
- ICP fit: [details]
- Trigger event: [details]
- Relationship: [details]

KEY STAKEHOLDERS:
- [Name], [Title] - [Role in buying]
- [Name], [Title] - [Role in buying]
- [Name], [Title] - [Role in buying]

ACCOUNT INTELLIGENCE:
- Business priorities: [from research]
- Technology stack: [tools they use]
- Competitive: [current solutions]
- Challenges: [pain points]

OUTREACH PLAN:
Week 1: [Actions by stakeholder]
Week 2: [Actions by stakeholder]
Week 3: [Actions by stakeholder]

SUCCESS CRITERIA:
- Meeting with [stakeholder] by [date]
- Discovery completed by [date]
- Opportunity created by [date]

Overcoming Prospecting Challenges

"I can't find the right contacts"

Solutions:

  • Use multiple data sources
  • Leverage LinkedIn connections
  • Research press/content for names
  • Call into company and navigate
  • Ask existing contacts for referrals

"No one responds to my emails"

Diagnose:

  • Is it deliverability? (Check spam folders)
  • Is it relevance? (Review messaging)
  • Is it targeting? (Validate ICP)
  • Is it timing? (Test send times)

Fix:

  • More personalization
  • Better subject lines
  • Shorter emails
  • Clearer value prop
  • Different angles

"I'm getting ghosted after initial response"

Solutions:

  • Respond faster (under 1 hour)
  • Be more specific in follow-up
  • Provide value in each touch
  • Make it easy to say yes or no
  • Multi-channel follow-up

"I don't have enough time for prospecting"

Solutions:

  • Block dedicated prospecting time
  • Batch similar activities
  • Use templates and sequences
  • Prioritize ruthlessly (tier 1 first)
  • Automate where possible

Prospecting Cadences by Segment

Enterprise Prospecting

Characteristics:

  • Longer sales cycles
  • Multiple stakeholders
  • Higher personalization required
  • Account-based approach

Approach:

  • Deep account research
  • Multi-threaded outreach
  • Executive engagement
  • Longer, more patient sequences
  • Focus on quality over quantity

Mid-Market Prospecting

Characteristics:

  • Medium sales cycles
  • Smaller buying committees
  • Balance of personalization and scale
  • Mix of inbound and outbound

Approach:

  • Segmented sequences by persona
  • Moderate personalization
  • Phone as key differentiator
  • Faster follow-up cadence
  • Clear qualification criteria

SMB Prospecting

Characteristics:

  • Short sales cycles
  • Often single decision-maker
  • Price-sensitive
  • High volume required

Approach:

  • Templated sequences
  • Efficiency over personalization
  • Quick qualification
  • Self-serve options when appropriate
  • Volume with smart targeting

Measuring Prospecting Success

Leading Indicators

Track weekly:

  • Activity volume (emails, calls, LinkedIn)
  • Response rates by channel
  • Conversation rate
  • Meetings booked

Lagging Indicators

Track monthly:

  • Pipeline generated from outbound
  • Outbound meeting show rate
  • Outbound opportunity rate
  • Outbound win rate
  • Revenue from outbound

Prospecting Scorecard

Metric Target Actual Trend
Accounts researched
Contacts added
Sequences started
Emails sent
Calls made
Response rate
Meetings booked
Pipeline created

Questions to Ask

If you need more context:

  1. Who is your ideal customer (ICP)?
  2. What's your current prospecting approach?
  3. What tools do you have access to?
  4. What's your meeting/pipeline goal?
  5. What's working and what isn't?
  6. How many reps are doing outbound?

Related Skills

  • cold-outreach-writing: For email and message templates
  • sales-outreach-sequences: For multi-touch campaign design
  • discovery-calls: For converting meetings to opportunities
  • lead-qualification: For qualifying prospects effectively
  • account-planning: For strategic account approach
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