Vistage Outreach Campaign Builder

Build a complete, ready-to-execute multi-touch outreach campaign for a specific Vistage prospect. Generates personalized emails, LinkedIn messages, value-bomb content, conversion messages, timing calendars, subject line options, objection responses, and tracking metrics — all in a copy-paste-ready playbook. Use whenever a Chair says "create an outreach campaign for [name]", "write outreach for this prospect", "help me reach [name]", "build a campaign", "draft messages for [name]", "write an email to this CEO", "LinkedIn message for a prospect", "follow-up sequence", "drip campaign for a prospect", "how should I reach out to [name]", or any request to create actual outreach messages for a specific executive. Works best when paired with the Prospect Intelligence Brief skill — run that first to research the prospect, then use this skill to operationalize the insights into a campaign. Also trigger when a Chair has already described a prospect in conversation and wants to create outreach.

If the prospect has already been researched in this conversation (via the Prospect Intelligence Brief or earlier discussion), pull from that context. Don't re-research — operationalize.

Step 2: Strategic Profile (Brief)

Before writing messages, synthesize a brief strategic profile of the prospect. This isn't the full intelligence brief — it's the messaging-relevant extract:

Current pain points (2-3 specific challenges based on their company stage and role) Communication style (DISC inference: how do they prefer to receive information?) Decision triggers (what would make them act nov ss later?) Likely objections (the 1-2 things they'll push back on) Emotional landscape (what are they feeling? Overwhelmed? Ambitious? Isolated? Skeptical?)

This profile drives every message decision — tone, length, evidence type, ask size.

Step 3: Campaign Architecture

Design the campaign structure before writing any messages.

The Standard 5-7 Touch Campaign (3-4 weeks)

Timing Principles

• Best days for executive email: Tuesday, Wednesday, Thursday
• Best times: 7:00-8:00 AM (pre-meeting scan) or 8:00-9:00 PM (evening review)
• Avoid: Monday morning (inbox triage mode), Friday afternoon (checked out)
• LinkedIn messages: Early morning or late evening — when they're scrolling, not working
• Space between touches: Never less than 2 days. Executives feel pressure quickly. Respect the cadence.

Channel Strategy

• Email: Best for substantive content, insights, and formal asks. Use when you have their email.
• LinkedIn: Best for relationship building, casual engagement, and visual presence. Lower barrier.
• Phone: Best for warm prospects after 2-3 touches, or when referred ("Sarah suggested I call"). Never cold call a CEO — it starts the relationship on their back foot.
• In-person: Best as the culmination, not the opening. "Coffee" or "guest day" is the close, not the outreach.

Customize the channel mix based on what you know about the prospect. A 40-year-old tech CEO lives on LinkedIn. A 60-year-old manufacturing owner checks email and takes phone calls.

Step 4: Write the Messages

Message 1: The Opening (Email)

This message determines whether they ever read another one. It must:

1. Open with a hyper-personalized, researched insight about THEIR specific situation
2. Create immediate relevance by connecting to their current context
3. Demonstrate understanding without presumption
4. Introduce a question or insight they haven't considered
5. Offer value without asking for anything
6. Close with a soft, no-commitment prompt

Framework: Noticed-Wondered-Hypothesis

• "I noticed [specific observation about their business/industry]..."
• "It made me wonder [a question or insight that connects to their situation]..."
• "My hypothesis is [a perspective they might not have considered]..."

Rules:

• Under 150 words. Executives scan — earn the read in the first line.
• No "Dear [Name]" — use their first name or just jump in.
• No "I'd love to introduce myself" — nobody cares about your introduction.
• No "I hope this email finds you well" — delete this from your vocabulary.
• No pitch. Not even a subtle one. Pure value.
• Subject line: Specific and intriguing, not clickbait. Reference their company or situation.

Subject line options: Provide 3 A/B test options:

• One referencing their specific business situation
• One asking a provocative question
• One referencing a peer pattern or trend

Example structure (adapt to the specific prospect):

Subject: [Specific to their situation]

[First name] —

[One sentence: specific observation about their business or industry — shows you've done homework]

[One sentence: the insight or question this raises]

[Two sentences: a relevant pattern you've seen across similar companies, or a framework that applies]

[One sentence: offering a resource, insight, or perspective — no strings]

[One sentence: soft close — "Curious whether you're seeing the same thing" or "Happy to share more if useful"]

[Signature — just name, no title block on first touch]

Message 2: LinkedIn Connection Request

300 characters maximum. Every character counts.

Structure:

• Ultra-personalized reference to their work, achievement, or content
• Subtle signal of shared interest or relevant perspective
• No pitch, no "I'd like to tell you about..."

Example structure: "[First name], your [specific thing — post, achievement, company milestone] caught my eye. I work with CEOs in [their region/industry] navigating similar [challenge/opportunity]. Would welcome the connection."

Message 3: LinkedIn First Message (After Connection)

Warm, conversational, value-forward. This arrives in their LinkedIn inbox after they've accepted your connection.

Structure:

• Thank them for connecting (one sentence, not obsequious)
• Share a relevant insight or resource — genuinely useful, no strings
• Reference a specific challenge in their industry
• Mention an anonymized peer success story that mirrors their situation
• Invite their perspective, not a meeting

Rules:

• Brief and scannable — break into 2-3 short paragraphs
• Value in every sentence
• Ask for their OPINION, not their TIME
• Position yourself as a peer resource

Messages 4-5: Value Bombs

These are pure value delivery — no ask, no pitch, no agenda. Each one builds your authority and creates reciprocity.

Each value bomb delivers:

1. A counterintuitive insight about their specific business challenge
2. A framework or tool they can immediately apply
3. An anonymized case study of a peer company solving a similar issue
4. A provocative question that reframes their thinking

Format options (choose based on the prospect's communication style):

• "Quick thought on [specific company initiative]" — for D-types who want directness
• "Saw this and thought of your [specific challenge]" — for I/S-types who value connection
• "3 things CEOs in [their industry] are doing differently" — for C-types who want substance

Rules:

• Takes less than 30 seconds to consume
• Provides standalone value (even if they never respond, they got something useful)
• Builds authority without claiming it (show, don't tell)
• Creates a breadcrumb trail toward peer advisory value (the insights naturally lead to "I get this kind of thinking from my peer group")

Message 6: The Pivot Message (Conversion)

This is the pivotal message that moves from value delivery to a specific ask. It only works because value has been established.

Structure:

1. Reference the value already shared —""I've enjoyed sharing perspectives on [topic]..."
2. Introduce controlled urgency — an upcoming event, a group forming, a specific relevant topic at the next meeting
3. Make the ask incredibly specific and easy —" no "Would you like to meet?" but "I'm hosting a 90-minute roundtable on [topic] on [date]. Six CEOs, no pitch, real conversation. Would that interest you?"
4. Offer multiple response options — "You could join the roundtable, or if you'd prefer, I'd be happy to share the key insights afterward." Multiple options increase the probability of a yes.
5. Include a negative option that still provides value — "And if the timing doesn't work, I'll send you the summary — it'll be worth 5 minutes of reading."

Psychclogical triggers (deployed subtly, not manipulatively):

• Loss aversion: "The CEOs who figure out [challenge] this year will have a 2-3 year lead on those who don't"
• Social proof: "Several CEOs in your space are already working through this"
• Scarcity: "I keep the group to [number] so everyone gets airtime"
• Authority: Demonstrated through the value you've already delivered, not claimed
• Consistency: "Based on your thinking about [topic they've discussed], this seems like natural next step"

Message 7: The Graceful Close (If No Response)

Never end a sequence on a desperate note. End with dignity, value, and an open door.

Structure:

• Acknowledge you've been in touch and respect their time
• Offer one final piece of value
• Make clear there's no hard feelings
• Leave the door explicitly open
• Optional: Ask for a referral ("Who else in your network might find value in this kind of peer exchange?")

The key line: "If the timing isn't right, I completely understand. I'll stay in your orbit and share things I think you'd find valuable. No agenda."

Step 5: Contingency Responses

Prepare responses for common prospect replies:

"Thanks, but I'm too busy right now." Response: Acknowledge, validate, offer minimum-commitment alternative. "Completely understand — the leaders I work with are all in the same boat. That's actually part of what makes [a 90-minute roundtable / a quick call] valuable — it forces strategic thinking time that gets squeezed out. But timing matters. When would be better to revisit — Q2 or Q3?"

"How much does it cost?" Response: Don't dodge it, but contextualize. "Annual investment is [amount]. Most members tell me the ROI is 5-10x within the first year, usually from one or two decisions they made differently because of the group. Happy to share some specifics. But honestly, I wouldn't want you to evaluate cost until you've experienced a meeting — would a guest day help you assess whether the value is there?"

"I'm already in [EO/YPO/advisory board/coaching]." Response: Complementary, not competitive. "That's great — [EO/coaching/etc.] provides [specific value]. This is different because [specific differentiator]. Most members have both because they serve different needs. The best way to feel the difference is a guest visit. Open to it?"

"Send me some information." Response: This is usually a polite deflection. Don't just send a brochure. "I'd be happy to. But I've found that information about peer advisory doesn't really convey the experience — it's like reading about exercise vs. actually working out. Would you be open to a 20-minute call where I can learn about your situation and share what's most relevant? If not, I'll send a few things I think you'd find genuinely useful."

"Let me think about it." Response: Respect it, but get specific. "Of course — this is a significant commitment and it should feel right. What specifically would help you decide? Is it a question about [time/fit/value/members]? Happy to address whatever would be most helpful."

"I don't think this is for me." Response: Graceful exit with future optionality. "I appreciate you being direct — I respect that. If anything changes, the door is always open. And if you know someone who IS wrestling with [specific challenge you've discussed], I'd welcome an introduction. Either way, it's been good connecting."

Step 6: Assemble the Campaign Playbook

Output Format

Compile everything into a single, action-ready document:

1. CAMPAIGN OVERVIEW

• Prospect name and key facts (one paragraph)
• Campaign strategy summary (what we're doing and why)
• Expected timeline (start to close)
• Success metrics

2. COMPLETE MESSAGE TEXTS All messages, fully written, copy-paste ready:

• Email 1: The Opening (with 3 subject line options)
• LinkedIn Connection Request
• LinkedIn First Message
• Value Bomb 1
• Value Bomb 2
• The Pivot/Conversion Message (with 3 subject line options)
• The Graceful Close (with 3 subject line options)

3. TIMING CALENDAR Specific dates/days for each touch, based on when the campaign starts:

• "Day 1 (Tuesday): Send Email 1 at 7:15 AM"
• "Day 3 (Thursday): Send LinkedIn connection request"
• etc.

4. CONTINGENCY RESPONSES Pre-written responses for the 5-6 most likely prospect replies, customized to this specific prospect.

5. PERSONALIZATION NOTES [Brackets] around anything the Chair should verify or customize further. Flag spots where personal knowledge of the prospect could sharpen the message.

6. TRACKING GUIDE What to measure:

• Open rates (if email tool supports it)
• Response rates by touch
• LinkedIn profile views after touches
• Time from first touch to conversation
• Conversation to guest day conversion

7. QUICK START GUIDE

• First 3 actions to take today
• Key success indicators to watch for
• Common pitfalls to avoid (e.g., "Don't follow up the same day if no response," "Don't connect on LinkedIn and message simultaneously")

8. CONFIDENCE SCORE Rate the campaign 1-10 based on:

• Prospect fit quality
• Personalization depth
• Channel-message match
• Timing appropriateness
• Overall likelihood of response

Explain your reasoning. Honest assessment helps the Chair calibrate expectations.

Principles

1. Peer-to-peer or nothing. The moment a message smells like a sales pitch, it's dead. Write as if one CEO is sharing a thought with another. No "I'd love the opportunity" or "I think you'd benefit from..." — these are vendor phrases.

2. Specificity is credibility. Generic messages get generic responses (or none). Reference THEIR company, THEIR industry, THEIR situation. The specificity proves you've done the work.

3. Value first, ask later. The first 3-4 touches should deliver genuine value with zero strings. The ask only earns the right to exist because value preceded it.

4. Every message earns the next one. Each touch should make the prospect WANT to hear from you again. If any message feels like an interruption rather than a contribution, rewrite it.

5. Brevity is respect. Executives have 30 seconds for your message. Under 150 words for emails. Under 100 for LinkedIn messages. Say more with less.

6. The close is an invitation, not a pitch. You're not selling a product. You're offering membership in something exclusive. The posture should be: "I think you'd add value to this group AND get value from it. Let me show you."

7. Dignity in the exit. How you handle rejection determines whether they refer. A graceful "no hard feelings" close generates more future pipeline than a pushy "but wait" follow-up.

8. Write for THIS person. Campaign templates are starting points. The value is in the customization. If a message could be sent to any CEO without changes, it's not good enough.