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Automating Follow-Up Messages: Streamlining Your Sales Process

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Automating follow-up messages with AI I identified a good pitch that converts well, the general flow:

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Send connection request
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Once they accepted, send my pitch and ask if I can send more information
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Often they reply, “Yes, send it over. I’m curious”
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Next, I send over a similar message each time, and asking for a meeting to discuss further with 2 relevant dates
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When they reply, I want to schedule something in my calendar i.e. using Calendly.

Since all of this is 90% of the times the same, only some small things are changed in the copy, I want to automate the whole follow-up sequence up until booking an actual call with AI. What would be the best, cheapest and fault proof way to approach this? Also, in case the reply of the lead is not something like: “Yeah I’m interested”, I want to escalate it to a human. So I can remain in control and 90% of the repetitive work gets automated. In case escalating to a human makes it much too complex to build, can also leave it out for now and just leave it 100% to the AI. Thanks in advance 🙏🏻

2 comments

Channeled
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For automating your LinkedIn follow-up sequence, I recommend using Clay with Twain integration. This allows you to: 1. Create multi-step sequences (up to 4 steps) that maintain consistency while personalizing each message 2. Set up automated workflows that span different platforms (LinkedIn, email) for comprehensive outreach 3. Use AI to generate personalized messages based on prospect data For non-standard responses requiring human intervention, you can implement lead scoring to filter qualified leads and automate responses only for standard replies. For scheduling integration, you can connect Clay to your email tools and CRM through native integrations with platforms like Smartlead, Instantly, and others.
Sources: Create Multi-Step Sequence Messaging with Twain - Clay University Claybooks: Automate multi-step sequence messaging with Twain | Clay.com Automated Omnichannel Outreach Via Social Media and Emails With La Growth Machine [Automated Outbound] - Clay University FAQ | Clay.com Reply.io x Clay integration | Clay.com
Bo (.
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Hey — for this kind of workflow, tools like Heyreach or Growth Machine are solid options. They’re built to handle connection requests, automated follow-ups, conditional logic based on replies, and booking flows with tools like Calendly. They also let you set rules to escalate replies to a human when the response doesn’t match your “interested” intent. Might be worth testing one of them to see which fits best with your process. Let me know if you want help thinking through the setup.

Automating Follow-Up Messages: Streamlining Your Sales Process | Clay