If you’re tired of sending emails into the void and chasing responses by hand, you’re not alone. Most people don’t reply to the first message—usually, it’s the polite nudge that gets their attention. That’s where automating follow-up reminders in Overloop comes in. This guide is for sales reps, founders, recruiters, or frankly anyone who needs more replies without living in their inbox. I’ll walk you through setting up actual, useful automations—plus what to skip, and how to keep things human.
Why bother automating follow-ups?
Here’s the reality: most of your first cold emails won’t get a response. It’s not personal. People are busy, forgetful, distracted, or just not ready—until you remind them.
Relying on your memory or a sticky note system is a recipe for missed deals and wasted effort. Automating reminders means:
- You don’t drop the ball, even when you’re swamped.
- Prospects get timely nudges—without you hovering.
- You get data on what works (and what’s just annoying).
But automation isn’t magic. If your follow-ups are robotic or too frequent, people will tune out—or worse, hit “report spam.” Balance is key.
Step 1: Get your basics set up in Overloop
Before you even think about automating, make sure your Overloop account is ready for action.
- Import your contacts: Make sure your list is clean. Bad emails = bounces = trouble.
- Connect your email account: Overloop can send from your real inbox (Gmail, Outlook, etc.), which helps with deliverability. Do this first.
- Organize prospects: Use tags or segments. The more organized you are, the easier it is to target follow-ups.
Pro tip: Don’t overthink your lists at the start. You can always tidy up as you go. Start with your warmest leads, or the batch you care most about.
Step 2: Build your first campaign (don’t get fancy yet)
Overloop calls automated outreach “campaigns.” This is where you’ll set up your initial email and the follow-up reminders.
Here’s how to start:
- Create a new campaign.
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Give it a name that actually means something. “Q2 Warm Leads” beats “Campaign 14.”
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Add your contacts.
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Select the segment or tag you want to target.
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Write your first email.
- Keep it short and clear. Skip the fluff.
- Personalize with merge fields (like {{first_name}}) but don’t go overboard. If it reads like a robot filled in the blanks, people notice.
What to ignore: Those “AI rewrite” buttons can be tempting, but they often spit out generic nonsense. Trust your own words.
Step 3: Set up automated follow-up reminders
Here’s where the magic happens: adding scheduled follow-ups that only send if you haven’t received a reply.
How to do it in Overloop:
- Add a follow-up step.
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In your campaign builder, click “Add Step” after your first email.
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Choose the trigger:
- Set it to send “if no reply” after X days.
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Standard timing: 2–4 business days is safe. Shorter feels pushy; longer gets forgotten.
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Write your follow-up message.
- Be direct. Reference your last email.
- Keep it friendly and low-pressure.
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Example:
> “Just checking in to see if you had a chance to look at my earlier note. Let me know if you have questions.” -
Repeat for more follow-ups (optional).
- Most effective campaigns have 1–2 follow-ups. Three max. After that, you’re just pestering.
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Change up your wording each time. Don’t send the same message twice.
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Set time and days.
- Only send during business hours, and avoid weekends. Overloop lets you schedule sending windows. Use them.
Pro tip: If you’re worried about being annoying, you probably aren’t. It’s the people who never think about it who send twelve emails in a row.
Step 4: Use tasks for manual reminders (when automation isn’t enough)
Automated emails work for the bulk of follow-ups, but some situations call for a human touch. Overloop lets you set up tasks as reminders for yourself.
- When to use tasks:
- High-value leads
- Deals that have gone cold after multiple emails
- When you want to call, send a LinkedIn message, or do something more personal
How to add a reminder task:
- In your campaign, add a “Create Task” step after a follow-up.
- Set the task type (call, LinkedIn, custom) and due date.
- You’ll see these pop up in your Overloop dashboard so you don’t forget.
Don’t over-automate. If you treat everyone the same, your results will tank. Use tasks for the important stuff.
Step 5: Review, tweak, and don’t set-and-forget
Automation is only useful if it’s actually getting you more replies. Don’t just activate your campaign and walk away for a month.
- Check your reply rates weekly. Overloop will show you:
- Who replied (and when)
- Which follow-up got the response
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Who’s ignoring you entirely
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If response rates are low:
- Shorten your emails.
- Change your subject lines.
- Space out your follow-ups more.
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Try a different call-to-action (“Is this interesting?” vs. “Are you the right person?”).
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If you get angry replies:
- Shorten your sequence.
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Make opt-out easy.
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Don’t obsess over open rates.
With privacy changes, open rates are less reliable than ever. Focus on actual replies.
What works, what doesn’t, and what to ignore
What actually works: - Short, clear emails. - 1–2 friendly, spaced-out follow-ups. - Personalization, but only where it makes sense. - Manual tasks for big deals.
What doesn’t: - Sending five-plus follow-ups. You’ll just annoy people. - Spammy subject lines (“Quick question!” three times in a row). - Relying only on automation for complex sales—relationships still matter.
Ignore: - “Growth hacks” that sound too good to be true. They usually are. - Templates that make your emails sound like everyone else’s. - Over-complicating your workflows. Simple beats fancy nine times out of ten.
Keep it simple and iterate
Automating your follow-ups in Overloop isn’t about tricking people into replying—it’s about not letting opportunities fall through the cracks. Start with one campaign, keep your messages human, and pay attention to what actually gets responses. You can always add bells and whistles later, but don’t let complexity slow you down.
Set it up, send it, watch what happens, and tweak as you go. That’s really all there is to it.
Good luck out there—and don’t let automation turn you into a robot.