What does this feature do?
Letterdrop helps you identify potential leads posting or engaging with content around topics you care about - like your company, competitors, or pain points. It can then automate personalized outbound to them on LinkedIn.
Why use it?
Timing is everything. Outreach tied to a recent post or relevant topic sees 3-4x better response rates than cold outreach. With this feature, you:
- Monitor conversations about your company, competitors, or related problems
- Engage leads while the topic is still top-of-mind
- Automate outbound while maintaining context and relevance
How do I get setup?
To set this up, go to Leads → Keyword Monitoring.
We recommend creating three main keyword groups:
- Your Company Name
- Competitors
- Customer Problems or Initiatives
Each keyword group includes:
- Keywords: What to track
- Prompts: Logic to evaluate if the post is worth engaging with (TRUE/FALSE)
Why Prompts?
Each keyword group can have a simple yes/no (TRUE/FALSE) prompt to help Letterdrop decide if a post is worth your attention. Think of this like giving instructions on what kinds of posts matter to you.
Keyword Best Practices
Letterdrop only scrapes the 50 most recent posts for each keyword everyday. So don’t put in super broad keywords like “engineering” or “salesforce” - there are too many people talking about them (probably a post every minute on these topics). To be sure your keywords will work, try to manually search for them on LinkedIn and look which gives you a manageable number of relevant results.
✅ Good keywords:
"zoominfo alternative", “zoominfo competitors”, “switching from zoominfo”, “hate zoominfo”, “churning zoominfo”
→ Fewer and targets high-intent users looking for a solution like yours.
❌ Bad keyword:
"zoominfo"
→ Too broad; results in noisy, less relevant posts.
Keyword Group Examples
🔹 1. Your Company
Track all posts that mention your brand-positive, negative, or neutral.
Example keyword: "Letterdrop" , any aliases/short names of your company are also important
Prompt:
If the post is not talking about [your company], the social selling platform solution, return FALSE. If the post seems to be from a current customer, return FALSE. Else return TRUE. Do not return anything except TRUE/FALSE
🔹 2. Competitors
Identify prospects exploring or comparing other solutions.
Examples:
"apollo alternatives"
"unhappy with zoominfo"
"gong vs clari"
Prompt:
If the post is complaining about them, return TRUE. If the post indicates the author is shopping around, comparing vendors, migrating away from their existing solution, or asking for suggestions, return TRUE. If the post is praising a competitor, return TRUE because we can still see where the competitor falls flat. Return FALSE in all other scenarios where there isn’t room for us to pitch and approach them, like if they are an employee at a competitor or if the post is announcing a partnership with a competitor or that they just signed on. Do not return anything except TRUE/FALSE
🔹 3. Problems Your ICP Faces
Monitor language related to pain points your product solves.
Examples:
"social selling"
"missed quota"
"pipeline visibility"
If there is either a direct or indirect way to tie the priorities in the post to the problems that [your company] solves and an executive in a real-world business context could plausibly connect the post to the solution provided by [your company] without needing a leap in logic, return TRUE. Else, return FALSE. Do not return anything except TRUE/FALSE
🔹 4. Events (Optional)
Track attendees of industry events your team is targeting.
Examples:
"SaaStr"
"Dreamforce"
"Pavilion GTM"
If the author looks like they're attending the conference or event, return TRUE. Else, return FALSE.
Advanced Tips
- Use quotes (
" ") for exact matches
- Use AND / OR operators to combine conditions
- Example:
(Zendesk AND ("unhappy" OR "alternative" OR "customer support"))
Automating Outreach via Workflows
Once keyword monitoring is active, automate prospect engagement from posts
Steps:
- Go to Workflows
- Create or edit a workflow
- Add Source: "Posted about a relevant topic"
- (Recommended) Add ICP filters
- (Optional) Filter by specific keyword groups
- (Optional) Add post filter: Only posts where prompt returned TRUE
- Add Actions: Like, Comment, Connect, DM, Slack, Webhook alert, etc.
Example setup:
Final Note
Start small-set up 5–8 keywords in each group, refine over time, and review engagement weekly. With the right setup, this becomes a powerful engine for timely, relevant prospecting.
Need help choosing keywords or writing prompts? Reach out to our team and we’re happy to assist.