📁 Sales

LinkedIn Outreach Prompt: Connection Note and DM Sequence

Write LinkedIn sales outreach from real prospect research: a short connection note, a first DM, two follow-ups, reply handling and a personalization audit.

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October 22, 2026

Prompt

Act as a B2B sales development rep who writes LinkedIn outreach by hand from real prospect research. Every line you write must trace back to something the user gave you, you never fake familiarity or invent results, and the messages are meant to be sent manually, not by automation tools.

Inputs:
- Prospect's name, title, company, and what the company does: [ProspectProfile]
- Something recent they posted, shared, or announced: [RecentActivity]
- What I sell, in one sentence: [MyOffer]
- One true proof point I am allowed to share: [ProofPoint]
- Any shared context (mutual connection, event, group, past contact): [SharedContext]
- What I want them to do next: [CallToAction]
- Limits (tone, words to avoid, industry rules): [Constraints]

Generate:
1. Relevance check: one or two lines on whether there is a real reason to reach out. If RecentActivity and MyOffer do not connect, say so and suggest what to research instead.
2. Connection note: under 200 characters, no pitch, tied to RecentActivity or SharedContext. Show the count.
3. First message after they accept: under 80 words, one question, no link.
4. Follow-up 1 (about 5 business days later): adds the ProofPoint and a low effort CallToAction.
5. Follow-up 2 (about 7 business days after that): a short, polite close that makes it easy to say no.
6. Reply handling: short answers for Interested, Not now, Wrong person, and Not interested.
7. Personalization audit: each specific detail in the messages, with the Input it came from.

Rules:
- Stop after two follow-ups.
- No fake compliments, no "I came across your profile," no invented mutual friends or numbers.
- If they say no or ask you to stop, the only reply is a thank you.

Instructions

Fill in a real recent post or announcement for each prospect, use one true proof point, and send each message yourself. Stop after the second follow-up. No scraping or automation tools; if you switch to email, follow CAN-SPAM.

Generated Output

This image was generated using the prompt above.

LinkedIn Outreach Prompt: Connection Note and DM Sequence - Result

Examples

Example Input

ProspectProfile: Jordan Lee, Head of Operations at Tarheel Movers, a regional moving company in Raleigh, NC with about 40 trucks.
RecentActivity: Jordan posted last week that they are hiring two dispatchers because Saturday moves keep overbooking crews.
MyOffer: Crew scheduling software for moving companies that books jobs against real crew and truck availability.
ProofPoint: a 25 truck mover in Charlotte uses us to plan Saturday crews, and their ops lead agreed to take reference calls.
SharedContext: we were both at the regional movers association meetup in Greensboro in September, but did not talk.
CallToAction: a 15 minute call, or I can send a 2 minute video of a Saturday schedule.
Constraints: friendly and plain, no hype words, never mention competitors by name.

Example Output

1. RELEVANCE CHECK
Real reason: Jordan is hiring dispatchers because Saturday moves overbook crews, and the software books jobs against real crew and truck availability. Worth reaching out.

2. CONNECTION NOTE (168 characters)
Hi Jordan, saw your post about Saturday moves overbooking crews. I work with moving companies on crew scheduling and was at the Greensboro meetup too. Happy to connect.

3. FIRST MESSAGE AFTER ACCEPT (56 words)
Thanks for connecting, Jordan. Your post about hiring two dispatchers stuck with me, since Saturday overbooking is the problem I hear most from movers. I work on crew scheduling software that books jobs against the crews and trucks you actually have that day. Is Saturday overbooking mostly a booking problem or a staffing problem for you?

4. FOLLOW-UP 1 (about 5 business days later)
Hi Jordan, one more thought on Saturdays. A 25 truck mover in Charlotte uses our software to plan their Saturday crews, and their ops lead is open to a quick reference call if that would help. If it is easier, I can send a 2 minute video of a Saturday schedule instead. Want me to send it?

5. FOLLOW-UP 2 (about 7 business days later)
Hi Jordan, I will leave it here so I am not cluttering your inbox. If Saturday crew scheduling comes up again while you are hiring dispatchers, I am glad to share that 2 minute video or set up 15 minutes. Good luck with the hiring.

6. REPLY HANDLING
- Interested: "Great. Does Tuesday or Wednesday work for 15 minutes? I can also send the 2 minute video first."
- Not now: "Understood. Would it help if I checked back after your new dispatchers start?"
- Wrong person: "Thanks, Jordan. Who handles crew scheduling at Tarheel Movers? I am happy to mention you pointed me their way, or not, your call."
- Not interested: "Thanks for letting me know, Jordan. All the best."

7. PERSONALIZATION AUDIT
| Detail used | Source |
|---|---|
| Saturday moves overbooking crews | RecentActivity |
| Hiring two dispatchers | RecentActivity |
| Greensboro meetup | SharedContext |
| Books jobs against real crews and trucks | MyOffer |
| 25 truck mover in Charlotte, reference call | ProofPoint |
| 15 minute call, 2 minute video | CallToAction |
| Tarheel Movers | ProspectProfile |

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