If you run a sales team, you know the follow-up game is where deals are won or lost. But who has time to chase every lead manually? This guide is for anyone who's tired of mixing up reminders, dropping the ball on prospects, or just wants to stop nagging reps to send their follow-ups. Let's get your follow-up emails off your to-do list and into a system that actually works—without drowning in features you won't use.
We'll walk through automating follow-up sequences in Mailscale. I'll cover what works, what doesn't, and how to avoid the rookie mistakes that make automated emails feel like spam. If you're looking for magic shortcuts, look elsewhere. If you want practical steps that save real time, read on.
1. Get Clear on Your Follow-Up Goals
Before you jump into templates and triggers, be honest: What do you actually want your follow-ups to do? Is it about booking calls, nudging deals forward, or just making sure leads don't go cold?
Start with these: - Define the main outcome for each follow-up sequence (e.g., “Book a demo,” “Get a reply,” “Nudge for contract signature”). - Think about timing—how many follow-ups make sense before you back off? - Decide how personal you want to get. Some sequences can be generic, but others need to sound like a real human wrote them.
Pro tip: If you can't sum up your goal in one sentence, your sequence is probably too complicated.
2. Map Out Your Sequence (On Paper First)
Don’t let the software dictate your process. Grab a pen or open a doc and sketch the bones of your sequence:
- Number of steps: How many emails, and how far apart?
- Branching: What happens if someone replies? What if they click a link but don’t respond?
- Stop conditions: When do you stop following up? (Unsubscribed, replied, bounced, etc.)
Example: 1. Day 1: Intro email 2. Day 3: Quick check-in (“Did you see my last note?”) 3. Day 7: Share a relevant case study 4. Day 12: Final nudge (“Should I close your file?”)
You don’t need fancy logic to start. Complicated flows look impressive in diagrams but often just confuse your team (and annoy your leads).
3. Set Up Your Follow-Up Sequence in Mailscale
Now that you know what you want to send and when, it’s time to build it in Mailscale. Let’s keep it simple but effective.
Step 3.1: Create a New Sequence
- Log in to your Mailscale dashboard.
- Go to “Sequences” (sometimes called “Campaigns”).
- Click “New Sequence.”
Give it a clear name—something like “Demo Request Follow-Ups.” Avoid clever names that only make sense to you. You’ll thank yourself later.
Step 3.2: Add Your Steps
- For each email step, paste your draft content.
- Set the delay (e.g., “Send 2 days after previous email”).
- Use placeholders for customization (e.g.,
{{First Name}},{{Company}}). But don’t overdo it—too much personalization can get awkward or break if your data’s messy.
Step 3.3: Set Stop Conditions
This is where most people mess up. If you keep emailing people who reply (or worse, unsubscribe), you’ll kill your credibility.
- In Mailscale, set rules to pause or stop the sequence if:
- The contact replies
- The email bounces
- The contact unsubscribes or marks you as spam
Double-check these settings. Automation is great until it embarrasses you.
Step 3.4: Test Before You Go Live
Send the sequence to yourself and a teammate. Check: - Spelling and formatting - That placeholders fill in correctly - That the timing feels right (don’t wait a week between emails if your sales cycle is short)
Catch anything weird before prospects do.
4. Add Contacts and Launch
You’ve got your sequence, now you need people to send it to.
Step 4.1: Import or Add Contacts
- Upload a CSV or connect your CRM if you’re feeling fancy.
- Double-check that fields like name and company line up with your placeholders.
Step 4.2: Assign to Sequence
- Select the contacts and add them to your sequence.
- Choose whether to start immediately or on a specific date.
Heads up: Don’t dump your entire lead list into a new sequence on Day 1. Start with a small batch so you can spot issues before they snowball.
5. Make Your Follow-Ups Sound Human (and Not Like a Robot)
Automation makes things easier, but it’s also how you end up in the spam folder. Here’s how to keep your emails from feeling canned:
- Write like you talk. Ditch the “Hope this email finds you well…” and get to the point.
- Short and clear wins. No one reads a wall of text from a stranger.
- Don’t fake personalization. If you don’t know something about the prospect, don’t pretend you do.
- Change up your subject lines. If every email is “Checking in,” it screams automation.
What to skip: Gimmicky merge fields (like mentioning the weather in their city) are more likely to backfire than impress.
6. Track Results and Tweak As You Go
No automation is “set it and forget it.” Even the best-written sequences get stale.
- Check your open, reply, and unsubscribe rates. If people aren’t opening, try new subject lines. If no one replies, your ask might be off.
- Watch for spam complaints. If these tick up, it’s a sign you’re being too aggressive or your list is bad.
- Ask your team for feedback. If they keep getting confused or prospects mention weird emails, something’s up.
Don’t be afraid to kill a sequence that isn’t working. Better to have one solid sequence than five mediocre ones clogging up inboxes.
7. What Works, What Doesn’t, and What to Ignore
Works: - Keeping sequences short (three to five emails max) - Clear, direct asks (“Can we set up a 15-minute call?”) - Stopping when people reply or unsubscribe
Doesn’t Work: - Writing a novel in each email - Sending more than five follow-ups (you just look desperate) - Scheduling emails at weird hours (unless you’re sure it fits your audience)
Ignore: - Over-engineering with conditional logic before you need it - Chasing every new feature Mailscale rolls out—stick to the basics until you’ve mastered them
Final Thoughts: Start Simple, Iterate Often
Automating your sales follow-ups in Mailscale isn’t rocket science, but it does take some upfront work. Build a sequence you’d actually want to receive. Launch with a small group, watch what happens, and keep tweaking. Most teams get bogged down trying to perfect things up front. Instead, just get started and improve as you go.
The best automation is the kind your leads never notice. Keep it human, keep it honest, and let the robots handle the boring stuff—so your team can focus on closing deals, not chasing reminders.