Actively AI vs Letterdrop
At their core, sales intelligence tools like Actively usually attempt two things:
- Find contacts worth reaching: instead of spraying a huge list, filter for people who show signals of interest (web behavior, mentions, CRM data, call cues)
- Automate outreach + follow-ups: generate personalized message drafts, schedule follow-ups, trigger actions based on responses, reduce manual sequence setup
Actively raised $22.5M in funding in April 2025, positioning itself as a challenger to prior AI SDR models by emphasizing reasoning over volume.
How does it compare to Letterdrop? Let's review.
Actively AI
Instead of reps trying to guess which companies to call or who might respond, Actively AI looks at all your existing data - CRM records, past calls, emails, public signals - and figures out which accounts or people are most likely to reply or buy.
It then hands your reps a prioritized “to-do list” with suggestions for who to reach out to, when, and with what message.
Over time, it watches which plays work and which don’t, and gets smarter so its recommendations improve as you use it.
Key Features
- Surfaces the right accounts and contacts
- Suggests timing and message ideas
- Learns from your own data for tailored results
- Integrates with CRM and sales tools
- Improves over time with feedback
- Automates busy work like list cleanup and enrichment
- Meets enterprise security standards (GDPR, SOC 2)
Letterdrop
Letterdrop similarly addresses the challenge of helping teams identify contact-level prospects to reach out to, and adds a layer of execution.
Instead of stopping at recommendations, it actually moves contacts through automated workflows, drafting and delivering outreach inside the tools reps already use.
To summarize, Letterdrop:
- Surfaces real contacts showing intent from CRM, sales calls, web activity, and social signals
- Adds context before outreach so messages tie back to what the contact actually said or searched
- Auto-drafts tailored messages using that context (including live web search), so outreach feels personal and relevant
- Pushes into Apollo, Outreach, and other systems automatically, turning intent into actual outbound.
It also can also automatically revive closed-lost deals if you're interested in that.
Actively AI vs Letterdrop
| Feature | Actively | Letterdrop |
|---|---|---|
| Contact-level enrichment | Surfaces high-propensity accounts and contacts based on CRM, call logs, and external signals | Surfaces real contacts showing intent across CRM, calls, web, and social activity |
| Context for outreach | Provides “why now” reasoning and suggestions for next steps | Adds detailed context from signals + live web search to inform outreach |
| Message drafting | Suggests timing and message ideas | Auto-drafts tailored outreach rooted in actual signals and context |
| Workflow automation | Reps must act on recommendations manually | Automates outreach workflows directly into Apollo, Outreach, HubSpot, etc. |
| Follow up management | Continuous learning from outcomes, but follow-ups handled by reps | Automates reminders and follow-ups so reps don’t miss promised check-ins |
| Nurture | Focused on outbound execution and reasoning | Blends outbound with content/thought leadership automation to warm leads over time |
| Integrations | Connects into CRM, engagement platforms, call recording tools | Connects into CRM and outbound tools; workflows run in existing rep systems |
| Data learning | Custom model learns from past wins/losses to refine targeting | Learns from contact engagement and adjusts outreach + content suggestions |
| Security | SOC 2 Type II, GDPR, CCPA compliance | SOC 2 Type II, GDPR, CCPA compliance |
In all honesty, it's a close one.
Both Actively and Letterdrop promise to help your team find the right people to reach and automate parts of the outbound process. The difference is in how far they actually take you from “signal” to action.
If you want to take your outreach from signal to execution all the way through, let us know.
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