If you’re running sales or recruiting, you know the pain of sending the same email over and over—and getting nothing back. The fix? Automated email sequences. They’re not magic, but if you set them up right in Outreach, you’ll spend less time chasing ghosts and more time having real conversations. This guide is for anyone who’s tired of guesswork and wants a setup that actually gets replies.
Why Bother With Automated Sequences?
Let’s be blunt: Most cold emails get ignored. People are busy, and generic templates make them hit delete even faster. Automated sequences help you:
- Follow up without dropping the ball
- Personalize (a little) at scale
- Test what actually works instead of hoping
But—and it’s a big but—automation can backfire if you treat it as a spam cannon. The goal here is to use Outreach to make your life easier without annoying your prospects. Let’s get into the practical steps.
Step 1: Nail Down Your Goals (Don’t Skip This)
Before you even log in, ask yourself what you want from these emails. Seriously—writing “Book a demo” and “Just checking in!” isn’t a strategy.
- Pick one clear call to action. Are you asking for a meeting, feedback, or something else? Don’t try to do it all.
- Know your audience. Who are you emailing? What do they care about? (Hint: Not your quarterly targets.)
- Set realistic expectations. If you’re cold-emailing, a 10% reply rate is actually pretty good.
Pro Tip: Write your “ideal reply” on a sticky note. If your sequence doesn’t make it easy for someone to send that reply, start over.
Step 2: Organize Your Contacts
Garbage in, garbage out. If your contact list is messy, your results will be too.
- Clean your list. Remove bounced emails, duplicates, and people who’ve already replied.
- Segment by persona or stage. Outreach lets you create folders or tags. Use them. Don’t send the same message to a CEO and a junior analyst.
- Double-check opt-outs. Nothing will get you blocked faster than ignoring a “remove me” request.
What to skip: Don’t waste hours researching every single lead. Do enough to personalize the first line or mention something relevant—then move on.
Step 3: Build Your Sequence in Outreach
Here’s where you actually use the tool. Outreach calls these “Sequences.” Think of them as a set of emails (and possibly calls or tasks) that go out on a schedule.
A. Create a New Sequence
- Go to Sequences in Outreach.
- Click “New Sequence.”
- Name it something obvious, like “Q2 Demo Request - Cold.”
B. Add Steps
Each step is an action—usually an email, but you can add calls or manual tasks.
- Step 1: The initial email. Keep it short and relevant.
- Step 2: Wait 2-4 days, then a follow-up email. Reference your last message, but don’t guilt-trip them.
- Step 3: Wait another few days. Send a final nudge or ask a different question.
- Optional: Add a manual task to check LinkedIn or call if you want to go multi-channel.
Sequence length: 3-5 steps is plenty. More than that, and you’re probably annoying people.
C. Write Your Emails (But Don’t Sound Like a Robot)
- Use {{first_name}} and other merge fields, but don’t overdo it.
- Open with something specific (“Saw you just raised funding—congrats”) if you can.
- Make your ask clear. “Would you be open to a quick call next week?”
- Ditch the fluff (“Hope you’re well!”) and skip long intros.
What doesn’t work: Copying templates from Google. They’re overused and easy to spot. Write your own, even if they’re simple.
Step 4: Set Your Sending Schedule
Timing matters, but not as much as people claim. Most replies happen during business hours, Tuesday–Thursday. That said:
- Spread out your emails. Don’t send everything in one week.
- Use Outreach’s send windows. This avoids sending at weird times (like 2 a.m.) that scream “automation.”
- Randomize a bit. Outreach can stagger sends to avoid spam filters.
Don’t bother with: Obsessing over the perfect hour. Content trumps timing.
Step 5: Test, Review, and Adjust
Here’s where most people drop the ball. Launching a sequence is just the beginning.
- A/B test subject lines and body copy. Outreach makes this easy. Try different openings and see what lands.
- Watch reply and bounce rates. If you’re under 5% reply, something’s off. Over 10% bounce? Clean your list.
- Check for weird replies. If people are confused or annoyed, your messaging needs work.
Pro Tip: Don’t change everything at once. Tweak one thing, then wait a week.
Step 6: Respect the “Human” Part
Automation saves time, but it’s not an excuse to be lazy.
- Reply quickly to real people. The whole point is to start conversations, not blast and ghost.
- Remove folks who reply. Outreach can do this automatically, but double-check it’s working.
- Don’t over-automate. If you’re sending 10+ touches with zero engagement, step back and rethink.
Ignore: Anyone who tells you to just “crank up the volume.” Bad emails to more people won’t help.
Step 7: Stay Out of Trouble
A few things to keep you out of spam filters and off blacklists:
- Warm up your sending domain. If it’s new, start slow—Outreach can help with this.
- Avoid spammy words (“free,” “guaranteed,” ALL CAPS).
- Include a real unsubscribe link. Outreach handles this, but make sure it’s in there.
- Monitor your sender reputation. If open rates tank, pause and investigate.
Hard truth: Even with all this, some people will mark you as spam. That’s life. Just don’t make it easy for them.
What to Ignore (And What Actually Moves the Needle)
- Ignore: Fancy HTML templates. They look like marketing blasts and get flagged.
- Ignore: Over-complicated branching sequences. Most sales teams never use them right.
- Focus on: Short, honest emails. Clear call to action. Basic personalization.
Quick Checklist Before You Hit Send
- [ ] Contacts are clean and segmented
- [ ] Sequence has 3-5 steps, spaced out
- [ ] Emails are plain text, not graphics-heavy
- [ ] Merge fields are correct (no “Hi {{first_name}},” fails)
- [ ] Unsubscribe link is included
- [ ] You’ve tested with a small batch
Keep It Simple—and Iterate
Don’t overthink it. Start small, see what works, and tweak as you go. The best automated sequence is one you actually use—and improve over time. Hype comes and goes, but smart, respectful outreach always wins. Good luck, and don’t forget: if in doubt, write like a human.