What you might be doing wrong
Your default plan with LinkedIn is probably something like:
- upload list of contacts
- set up template messaging
- send them all connection requests, then DMs or InMails depending on whether or not they accept
This generally doesn’t work and you are very likely to fail if this is your strategy.
Why the above doesn’t work
- If you have Sales Navigator, you can send 50 InMails/mo
- You can send a max of ~600 connection requests/mo
- If 20% of those accept your connection request (which is a big if), that means you can send 120 DMs/mo
- In total, you can send 170 messages/mo per person on LinkedIn
That’s not a lot of messages.
If you compare to email, where good cold campaigns get a 1-2% reply rate, that would yield 1-3 replies in a month and possibly zero booked meetings
This means:
- you can’t really run cold outbound campaigns and instead should only act on warm leads
- to improve the number of messages you can send, you need to maximize your connect rate
- to get replies, you need to maximize your message quality
How to actually run LinkedIn outbound (using Letterdrop)
Step 1. Segment your Lists to only work Warm Leads
Reach out when you have a reason to believe there’s a reason to reach out. This is what Letterdrop gives you.
Rule of thumb: If your first line can’t clearly explain why them, why now, don’t send it.
The other way to use LinkedIn is to put a face to a name. When you’re struggling to reach someone via email or phone, LinkedIn is a good trust building channel.
Use LinkedIn with email + calls (not instead of them)
Don’t use LinkedIn as your only outbound channel for cold leads. It’s most effective when it supports your sequence.
Letterdrop can automatically pull leads from your existing sequences in from Outreach, Apollo.io, HubSpot Dynamic Lists, and Salesforce Campaigns.
So you’ll be reaching leads via call and email, but also putting a face to a name on LinkedIn.
The goal is not necessarily to pitch them on the platform, but just get them to recognize you.
Step 2. Improve your connect rate to cold outreach
Be someone prospects want to connect with
If your profile doesn’t clearly explain who you help + how, it directly affects your connect rate in turn reducing the number of people you can DM.
If you look like an SDR who is going to pitch slap them immediately after connecting, why would they want to connect?
Lookup Playbooks Improve the LinkedIn Profile for your Sellers
Comment before you send a connection request
People don’t want to accept connection requests from people they don’t know.
Do this instead:
- Before sending a connection request, check to see if the lead posts on LinkedIn
- If they’ve posted in the last week, select that post.
- If they have a history of posting, but not recently, wait until their next post.
- Leave a thoughtful comment to build a relationship:
- Call out a specific point
- Add a useful perspective
Goal: make your name familiar so your connection request doesn’t feel random
Letterdrop can automate finding posts to comment on for you.
Add a good connection request message
Things that you can include in a connection request message that dramatically improve your odds of it being accepted:
- Reference a post they made that you commented on: “Nice post on tax implications for new factories. Got me thinking about domestic vs international expansion”
- Reference a coworker or report of theirs that you chatted with: “Just spoke with Sam about your AR overhead and she thought we should connect”
- Add value: “I found a bug in your newsletter that’s impacting deliverability - just wanted to share so you can fix it”
Goal: give them a reason to accept
You can use your favourite AI model in Letterdrop to generate personalised comments and connection requests for you.
Send video DMs
Most LinkedIn inboxes are flooded, and at this point everyone can use AI to create a “personalised message”
Text messages get skimmed or ignored. A short video DM stands out because it signals effort.
How to do it well:
- Keep it under 60 seconds
- Mention one specific observation
- End with one simple question (easy to answer)
- Avoid pitching - pitch after they respond and qualify themselves
Voice notes also work, but video DMs are usually better to put a face to a name.
Use it for warm leads or for people you’re already reaching out to via email and calls to put a face to a name.
If it’s too much effort, you can segment your campaign so that the same video makes sense for everyone on the list. Record once and re-use everywhere.
Goal: stand out to get seen
Letterdrop can make it fast and easy to read a script and record video DMs.
Quick checklist (before you DM)
✅ Your profile is strong (headline, about, credibility, CTA)
✅ You attempt to engage first (comment meaningfully)
✅ This is a warm lead with a clear reason to reach out
✅ Message is short, personal, and asks one easy question
✅ Using LinkedIn in addition to email/call sequence