Sales is mostly follow-up. The top reps aren’t magic—they’re just consistent. But let’s be honest: manual follow-up is a slog. You forget. Prospects slip through the cracks. It’s tedious, and nobody’s got time for that.
This guide is for anyone using Prosp who wants to automate follow-up emails without making it weird or robotic. We’ll walk through the nuts and bolts—what actually works, and what’s just marketing fluff.
Why bother automating follow-ups?
- Most deals need multiple touches. If you only email once, you’re missing out. Persistence wins.
- Manual follow-up sucks up hours. Reps should be selling, not sending “Just checking in!” emails all day.
- Consistency beats creativity. Automation makes sure your prospects don’t fall off your radar, even when you’re busy.
That said, automation isn’t magic. If your emails are boring or obviously canned, people will ignore you. The trick is to automate the process, not the personality.
Step 1: Get your follow-up content ready
Before you even touch Prosp’s automation features, nail down your follow-up messages. Don’t wing it.
What works: - Short, direct emails. Skip the fluff. No one reads a novel from a stranger. - Value in every message. Don’t just “circle back.” Offer a new insight, answer a question, or point to something useful. - A light touch. “Thoughts?” is sometimes all you need. Don’t guilt-trip or badger.
What to skip: - The “just bumping this up” approach, over and over. If you don’t add value, you’re training people to ignore you. - Templates that sound like templates. Write like a human, not a robot.
Pro Tip: Write 3-4 follow-ups in advance. Mix up the tone and content, but keep them consistent with your voice.
Step 2: Set up your pipeline in Prosp
Now, let’s get your follow-up sequence running in Prosp.
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Log in and head to Sequences.
In Prosp’s dashboard, find the “Sequences” or “Campaigns” tab—whichever your version has. This is where the magic happens. -
Create a new sequence.
Click “New Sequence.” Name it something obvious (e.g., “Inbound Demo Request Follow-up”). -
Add your emails.
For each follow-up, add a step: - Email 1: Your initial reach-out.
- Email 2: Scheduled to go out X days later (usually 2-3 days is fine).
- Email 3: Another 3-5 days later.
- Email 4: Final nudge, maybe a week later.
You can drag and drop the order, adjust timing, and tweak content as you go.
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Set the timing.
Don’t bombard people. Space your emails out. The default gaps in Prosp are usually fine—just double-check. -
Add conditions (if needed).
If you want to skip someone who replies, or only send certain emails to specific segments, set the rules now. Prosp has these options, but don’t overcomplicate it unless you need to.
What to watch out for: - Don’t set the sequence to run endlessly. Four to five emails is plenty. After that, let it go. - Make sure your sending window isn’t 24/7. Nobody wants a follow-up at 2am.
Step 3: Personalize…without making it a chore
The reason most automated emails flop? Zero personalization. The good news: Prosp lets you add merge tags (like {{first_name}} or {{company}}), so you can keep your messages feeling human.
How to do it: - Use merge tags for basics—name, company, maybe a recent activity. - Add a one-line custom note field if you want to drop in something specific about the prospect.
But… - Don’t try to fake deep personalization at scale. “I saw you went to Harvard” is creepy if you don’t actually care. - Always send yourself a test email. Make sure the merge tags work and your formatting isn’t weird.
Pro Tip: Batch your list, but add one little human touch to each. Even just referencing the last call or a detail from LinkedIn can make a difference.
Step 4: Add your leads and kick off the sequence
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Import your contacts.
You can do this by uploading a CSV or syncing your CRM. Map the fields (name, email, etc.) carefully—otherwise, your merge tags will break. -
Review before launching.
Double-check the list. Remove any bad-fit leads or people who’ve already replied. -
Start the sequence.
Hit “Start” or “Enroll Contacts.” Sit back and let Prosp do its thing.
What to skip:
Uploading a cold list scraped off the internet. That’s asking for spam complaints (and a bad sender reputation). Stick to warm or opted-in leads.
Step 5: Monitor replies (and actually respond)
Automation does the grunt work, but real sales still need a human touch. Make sure you’re tracking replies and jumping in fast.
- Prosp should pull replies into your inbox or CRM. Check daily.
- As soon as someone responds, stop the sequence for that contact—Prosp can do this automatically if you set it up right.
- Don’t keep automating after someone is engaging. Nothing kills deals faster than ignoring a real reply because “the system” kept running.
Pro Tip: Block 20 minutes a day to check and reply to follow-ups. The best automation is invisible—your prospects shouldn’t feel like they’re talking to a bot.
Step 6: Track your results and tweak
Here’s the honest part: your first sequence probably won’t be perfect. That’s fine. The beauty of automation is you can iterate quickly.
- Open and reply rates: Prosp tracks these for you. If nobody’s opening, try new subject lines. If nobody replies, your content needs work.
- A/B test subject lines or steps: But keep it simple. Don’t run five tests at once.
- Remove dead weight: If a follow-up step never gets replies, cut it.
- Watch your deliverability: If you see a spike in bounces or spam reports, pause and review your list and content.
What to ignore:
Don’t obsess over tiny percentage changes. Focus on big issues—getting more replies and conversations, not just opens.
What doesn’t work (and why)
- Aggressive follow-ups: Getting pushy just burns bridges. The “breakup email” works for some, but it can backfire.
- Over-automating: If you try to automate every touchpoint, you’ll end up sounding like a robot.
- Ignoring replies: If you don’t jump on real responses, all the automation in the world can’t help.
Keep it simple and iterate
Automating follow-up emails in Prosp isn’t rocket science, but it does take some thought. Set up a basic sequence, personalize lightly, and actually respond to people who engage. Don’t get lost in the weeds—start simple, see what works, and tweak as you go.
Automation’s job is to get you in more conversations, not to replace them. Keep things human, and let the software handle the boring parts. That’s how you boost real sales engagement—no hype required.