If you're doing B2B outbound, you already know the drill: research prospects, send cold emails, maybe a LinkedIn DM. Then the real grind starts—doggedly following up, logging tasks, and praying you don't let a hot lead slip through the cracks. Manual follow-up is the part nobody loves, but it's where deals actually get made.
This guide is for people who want to automate the soul-sucking parts of follow-up without turning their pipeline into a mess of canned spam. We'll walk you through using Canopy to set up smart, practical automations—enough to keep you sane, but not so much you lose control.
Why Automate Follow-Up Tasks?
Let’s be honest: following up manually is tedious, and the more prospects you add, the more likely something falls through. But automating everything blindly is a recipe for disaster—nobody wants to be on the receiving end of “Just checking in again!” for weeks on end.
Here’s what automation can do for you (if you use it with a little common sense):
- Save time. No more digging through your sent folder or sticky notes to remember who you need to ping.
- Reduce mistakes. The right follow-up at the right time, without dropping balls.
- Keep things moving. Prospects don’t get forgotten, and your pipeline doesn't stall.
But don't expect automation to close deals for you. It just gives you more at-bats.
Step 1: Get Clear on What to Automate (and What Not to)
Before you set up anything in Canopy, map out your current follow-up process. What do you do after a prospect gets your first email? What’s your usual cadence—1 day, 3 days, a week?
Automate: - Task reminders for follow-ups (so you don’t forget) - Creating follow-up tasks triggered by prospect actions (like opening or replying to an email) - Simple, time-based outreach nudges (e.g., “It’s been 4 days, send a quick check-in”)
Don’t Automate: - Complex, personalized responses (automation here feels robotic) - “Breakup” emails (“I guess you’re not interested?”) unless you’re sure they fit your voice - Overly aggressive multi-channel outreach (don’t spam people on every app)
Pro tip: Write out your follow-up steps on paper first. Most people try to automate a broken process, which just makes the mess bigger.
Step 2: Connect Your Tools and Set Up Your Canopy Workspace
Canopy isn’t magic—it needs access to your email, CRM, or sales engagement tool to be useful. The setup is pretty painless, but you’ll want to get your house in order first.
To get started:
- Sync your CRM or sales platform. Canopy works with common tools like Salesforce, HubSpot, Outreach, and Gmail. Connect your accounts so Canopy can see your deals and contacts.
- Import your outbound list. If you’re running outbound from a spreadsheet or CSV, import those contacts. Clean up duplicates before you do.
- Decide who gets automated follow-up. Not every lead should go into the same automation. Segment by deal size, industry, or source if needed.
Heads up: If your data is a mess—old contacts, missing emails—fix that first. Automation can’t fix garbage in, garbage out.
Step 3: Build Follow-Up Task Automations
Here’s where Canopy shines. Instead of just firing off emails, it creates tasks for you (or your team) based on what prospects do. It’s not about sending more emails—it’s about making sure the right person follows up at the right time.
Common automations that actually help:
- No-response reminders: If a prospect hasn’t replied in 3 days, auto-create a “Follow up with [Contact]” task.
- Engagement triggers: If someone opens your email 3+ times, create a “Call this prospect” task.
- Reply-based branching: If you get a positive reply, create a “Book meeting” task. If negative, create a “Mark as lost” task.
- Custom sequences: Set up multi-step task plans (e.g., Email > Call > LinkedIn DM) with delays you control.
How to set these up in Canopy:
- Go to the Automations section.
- Choose your trigger (e.g., “No reply after X days”).
- Select the action (“Create follow-up task for owner”).
- Add conditions (e.g., only for deals >$10k, or only for new leads).
- Test with a small batch before rolling out.
Honest take: Start simple. One or two triggers is plenty at first. You can always add more later, but if you try to automate every edge case, you’ll spend more time debugging than selling.
Step 4: Write Follow-Up Templates That Don’t Suck
Automating follow-ups doesn’t mean blasting the same “Hey, just checking in” to everyone. The best results come from teeing up thoughtful messages you can personalize quickly.
What works: - Short, relevant nudges (“Wanted to see if you had any questions about X”) - Referring to their last reply or activity (if you have that info) - Keeping it human—avoid sales clichés
What to skip: - Long, pitchy follow-ups (nobody reads these) - Guilt trips (“I’ve reached out three times…”) - Fake urgency (“This is my final attempt!”—it’s probably not)
How Canopy helps: When a follow-up task is created, Canopy can attach your template or draft, so you’re not starting from scratch every time. But make sure you actually review and tweak before sending—the fastest way to burn trust is to act like a robot.
Pro tip: Save your best custom responses as new templates over time. That way your automations get smarter without getting lazier.
Step 5: Monitor, Adjust, and Keep It Human
No automation is perfect out of the gate. The biggest mistake is “set it and forget it.” Check your results every week, and don’t be afraid to tweak or turn off automations that aren’t working.
What to watch: - Are prospects responding more, or less? - Are tasks piling up, or getting done? - Are you seeing more meetings booked, or just more noise?
If something feels off: - Adjust timing (maybe your follow-ups are too soon or too frequent). - Change your template copy. - Reduce the number of steps—sometimes less is more.
Don’t ignore your gut: If you wouldn’t want to get your own automated follow-ups, your prospects probably don’t either.
What to Ignore (Seriously)
- Endless “AI” promises: Canopy can automate workflows, but it isn’t going to write perfect personalized emails for you. Anyone who says otherwise is selling magic beans.
- Overcomplicated flows: If you need a flowchart to understand your automation, you’ve gone too far.
- Automating bad data: If your list is full of bad leads, automation just gets you ignored faster.
Keep It Simple, Iterate, and Don’t Lose the Plot
Automating your B2B follow-up with Canopy is about making your life easier—not about becoming a robot. Start with the basics, see what actually moves the needle, and add complexity only if you need it. The best automation frees you up to focus on real conversations, not more busywork.
Set up a few smart triggers, use templates as a starting point (not a crutch), and keep checking your results. If it feels too complicated, it probably is. Iterate as you go, and don’t forget: the goal is more closed deals, not more automated noise.