If you’re sending outbound emails, you already know: the first email rarely gets a reply. If you want real results, you need well-timed, relevant follow-ups—without losing your mind managing them. This guide is for anyone using outbound email, whether you’re in sales, recruiting, or just hustling for responses, and want to automate the “nudge” part of your outreach. We’ll walk through setting up automated follow up emails in Tryleap, keep it honest about what works, and help you avoid the rookie mistakes.
Why Bother With Automated Follow Ups?
Here’s the truth: most people ignore the first cold email. Not always because they’re not interested—life’s just busy, and inboxes are a mess. A smart follow-up feels human, shows persistence, and often gets the reply that would’ve otherwise slipped through.
Doing this by hand? Tedious and error-prone. That’s why tools like Tryleap exist. But before you dive in, know this: automation can help, but it won’t fix a bad message or a bad list. Get those right first.
Step 1: Get the Basics Sorted First
Before you even touch Tryleap, make sure you’re ready to automate. Here’s what you need:
- A clean, targeted list. Don’t blast everyone. Make sure your contacts are actually relevant.
- A clear goal. Are you booking demos? Chasing replies? Know what you want so your follow-ups aren’t just nagging.
- Your first email ready. Automation is for follow-ups, not the initial cold email. Nail that message first.
Pro tip: If your response rate is below 5% on the first email, work on your targeting and messaging before automating anything. Automation can make bad outreach worse, faster.
Step 2: Setting Up Your Tryleap Account
If you haven’t already, sign up for Tryleap. It’s pretty straightforward:
- Sign up or log in. Go to the Tryleap site and create an account.
- Connect your email. You’ll need to link your email provider (Gmail, Outlook, or whatever you use for outbound). Give it the necessary permissions.
- Set your sending limits. Don’t go wild—start small to avoid spam filters. Tryleap usually recommends something like 50-100 emails per day per inbox.
Heads up: If you’re sending big batches, warm up your sending domain (send lower volume for a couple of weeks first) or you’ll end up in spam, fast.
Step 3: Build Your Outbound Campaign
Now comes the meat of it.
3.1 Create a New Campaign
- In Tryleap, click “New Campaign.”
- Name your campaign something clear—trust me, you’ll thank yourself later when you’re running more than one.
3.2 Import Your Contact List
- Upload a CSV or connect your CRM (if you use one).
- Make sure your columns (First Name, Company, Email, etc.) match up—misaligned columns lead to embarrassing mail merges (“Hi , ”).
3.3 Set Up Your First Email
- Paste in your initial email template.
- Use personalization tags, but don’t overdo it. Nobody’s fooled by “{{FirstName}}” if the rest of your email is generic.
Step 4: Add Automated Follow Up Steps
Here’s where automation does its thing.
4.1 Decide on Your Follow Up Logic
You can set up several types of follow-ups in Tryleap:
- Time-based: Send X days after the last email if you haven’t received a reply.
- Conditional: Only send if the contact hasn’t replied or clicked.
- Sequenced: Build a series (e.g., 3-5 follow-ups, spaced a few days apart).
What works? Two or three follow-ups is plenty for most outbound. More than that and you risk being marked as spam—or just annoying people.
4.2 Write Your Follow Up Emails
Some honest advice:
- Keep them short. No one wants to read a novel, especially as a reminder.
- Don’t guilt-trip. “Did you get my last email?” is fine once, but gets old fast.
- Add value or context. Each follow-up should give a new reason to reply, not just “bumping this up.”
- Change your ask. If you’re not getting replies, maybe your ask is too big. Try a softer CTA in later follow-ups.
Example schedule:
- Day 0: Initial email.
- Day 3: First follow-up (quick nudge, maybe rephrase your value).
- Day 7: Second follow-up (share a resource or case study).
- Day 14: Last follow-up (polite close, “Let me know if now’s not a fit.”)
4.3 Set the Triggers in Tryleap
- In your campaign builder, add a new step for each follow-up.
- Choose the trigger (e.g., “3 days after no reply”).
- Paste your follow-up message.
- Review the sequencing and timing—don’t stack messages too close together.
Don’t overthink it: The default timing in Tryleap is usually fine. Tweaking an hour here or there rarely makes a big difference.
Step 5: Test Everything Before You Hit Send
This is where most people mess up.
- Send test emails to yourself (and a friend). Check for merge errors, formatting weirdness, and broken links.
- Check the unsubscribe link. It’s not just polite, it’s legally required in many places.
- Watch for spammy language. Avoid all-caps, too many links, or words like “FREE!!!”
Pro tip: Open your test emails on your phone. Half your audience will, and ugly formatting kills replies.
Step 6: Turn On the Campaign and Monitor Replies
Once you’re confident everything’s working:
- Activate the campaign. Tryleap will start sending based on your schedule.
- Monitor replies within Tryleap or your inbox. Make sure you reply personally to anyone who responds—you don’t want to automate those.
- Watch your stats: open rate, reply rate, bounce rate. If something looks off (way too few opens or lots of bounces), pause and investigate.
What not to obsess over: Open rates are getting less reliable thanks to privacy rules. Focus on actual replies.
Step 7: Fine-Tune and Iterate
No campaign is perfect out of the gate. Here’s what to tweak:
- Subject lines: If opens are low, try simpler, more human subject lines.
- Message content: If replies are low, is your ask clear and reasonable? Are your follow-ups adding value?
- Timing: If you’re getting marked as spam, space out your messages more.
Ignore the hype: There’s no “perfect” number of follow-ups or magic template. What works in one industry bombs in another. Don’t copy-and-paste guru advice—test small, see what works for your audience.
What to Watch Out For
A few ways outbound automation goes off the rails:
- Over-automation: If someone replies, make sure all further follow-ups stop. Nobody likes getting “just checking in” after they already responded.
- Personalization gone wrong: Double-check merge tags. “Hi {{FirstName}}” with blanks or misspellings is a dead giveaway you’re using a bot.
- Sending too much, too fast: Ramp up slowly. Sudden spikes look spammy to email providers.
Keep It Simple, Keep It Human
Setting up automated follow up emails in Tryleap isn’t hard, but it’s easy to make it more complicated than it needs to be. Focus on clear, honest messages, a reasonable schedule, and always reply personally when you get a real response. Start small, watch your results, and iterate. You’ll improve faster by sending a few thoughtful emails than by blasting a thousand templates.
Now go set up your campaign, and—just like your best follow-ups—don’t forget to check back in and see how it’s working.