How to Automate Sales Follow Ups

With dozens of opps in flight, reps can’t always remember every promised check-in. Dates slip, reminders get buried, and perfectly good prospects go cold.

Here’s how to put sales follow-up on autopilot, so every commitment to a buyer actually happens, right when it should.

How It's Usually Done

Here's how teams usually try to set up automatic follow-ups:

• CRM tasks & reminders (HubSpot, Salesforce) – great for logging, but reps still need to manually execute the outreach.
• Sales engagement platforms (Outreach, Salesloft) – powerful sequencing, but require reps to configure and can feel impersonal.
• Point solutions (AI notetakers, task managers) – capture follow-up notes but don’t always connect to outreach.

What Automated Follow-Up Systems Do

Tools that offer automated follow-up reminders for stalled deals usually focus on two things:

1. Reminder systems – automatically pinging reps when it’s time to re-engage based on what was said in the call.
2. Sequenced outreach – sending pre-scheduled emails or draft LinkedIn DMs if the rep doesn’t act.

This ensures that every stalled opportunity gets touched without manual tracking.

How Letterdrop Automates Follow-Up

Letterdrop integrates with your call software as well as with Apollo, Outreach, and any other outbound system.

That means:

• the rep responsible gets an email or Slack notification to follow up on the date the buyer mentioned in the call
• you can set up an automatic workflow that drafts and sends the follow up message via your outbound system
• if your rep forgets, there's a back-up option to route to another SDR or AE

We have a whole playbook on how to revive stalled opportunities or closed/lost deals.

‎

Ready to automate your follow-ups?

We can get you set up right away.

Talk to Us

Best Practices for Automated Follow-Ups

Even with automation, you’ll want to follow these guidelines:

• Always personalize – reference what the buyer said or the context of your last call.
• Don’t wait too long – if they said “3 months,” don’t let it drag to 6.
• Offer value – share a resource, insight, or update—not just “checking in.”

Final Word

If your reps are letting deals slip because they can’t keep track of every promised check-in, it’s time to put follow-up on autopilot.