If you’re a sales manager (or a rep tired of busywork), you know the real problem: nobody likes logging activities or remembering every follow-up. You want your team spending time talking to customers, not clicking around inside a CRM hoping not to drop the ball. This guide is for you. We'll break down how to use Setsail to automate follow-up tasks, cut down on manual effort, and—honestly—what’s worth automating vs. what just creates more digital noise.
Why Automate Follow-Ups, Anyway?
Let’s be real: most sales reps don’t forget to follow up because they’re lazy. It’s because they’re juggling a dozen deals, a dozen more “maybes,” and more admin than anyone wants to admit. Automating follow-up tasks can:
- Save hours of manual work per week
- Help reps keep deals moving (no more “oh crap, I forgot to ping them”)
- Make managers less likely to nag about CRM hygiene
- Surface real gaps—like stalled deals or neglected accounts
But automation isn’t magic. If you automate junk, you’ll get junk faster. So the key is to automate the right things and keep it simple.
Step 1: Decide What Actually Needs Automating
Before you start wiring up automation, take a breath. Not every email, call, or CRM field needs a follow-up task. Here’s what’s usually worth automating:
- Critical next steps: Scheduling a demo, sending a proposal, confirming a meeting.
- Time-based nudges: Reminding reps to check in if there’s been radio silence for X days.
- Deal stage transitions: When a deal moves to “Proposal Sent,” create a follow-up to confirm receipt.
- Renewals or QBRs: For existing customers, set reminders ahead of key dates.
What to skip:
Don’t automate every single activity. If your reps are drowning in auto-generated tasks, they’ll just ignore them. Focus on the stuff that makes deals move forward.
Pro tip:
Ask your reps where they actually forget stuff—don’t guess. They’ll tell you which follow-ups are slipping through the cracks.
Step 2: Get to Know Setsail’s Automation Features
Setsail isn’t trying to be another bloated CRM. Its automation tools are built to nudge reps on the stuff that matters and surface what’s falling through the cracks. Here’s what’s (actually) useful:
- Automated task creation: Setsail can create tasks based on triggers (like no activity on an account for X days, or deal moves to a new stage).
- Email and calendar integrations: It can monitor communication activity, so you’re not relying only on manual logging.
- Custom rules: You can set up logic like “If a contact hasn’t responded in 5 days, assign a follow-up task to the owner.”
What’s not so great:
If you try to automate every step (like “create a task every time a call is logged”), you’ll create more noise than value. Setsail is best used to flag real gaps, not micromanage every activity.
Step 3: Map Out Your Critical Follow-Up Moments
Don’t just turn on every automation knob. Map out the key moments in your sales cycle where a missed follow-up kills deals. Usually, these are:
- Right after a meeting: Did the rep send recap notes or next steps?
- After sending a proposal: Did the prospect open it? Did we follow up?
- When a deal goes cold: Has nobody talked to them in 7-10 days?
- Before contract renewals: Did we reach out in time?
Write these down. Be specific—“Follow up two days after demo if no reply,” not just “Follow up after demo.” That way, you can build laser-focused rules instead of a generic mess.
Step 4: Build Your Automations in Setsail
You’ve got your list of what matters. Here’s how to actually set it up in Setsail:
1. Log in and Find Automations
- Go to your Setsail dashboard.
- Look for an “Automations” or “Workflows” section. (If you don’t see it, check your permissions or ask your admin.)
2. Create a New Automation
- Click “New Automation” (or similar).
- Choose your trigger—this is the event that kicks things off. Examples:
- Deal moves to a new stage (e.g., “Proposal Sent”)
- No activity on an account for X days
- Meeting completed, but no follow-up email sent
3. Define the Action
- Most often, you’ll want to “Create Task” or “Send Reminder.”
- Write a clear task description—don’t just say “Follow up.” Try “Send proposal follow-up email if no reply by Friday.”
4. Set Conditions
- Limit automations to the right owners, teams, or deal types.
- Set time windows—e.g., only trigger during business hours.
5. Test Before Rolling Out
- Run the automation on a test deal or fake account.
- Make sure it doesn’t spam you with duplicate tasks or trigger at the wrong time.
- Ask a rep to sanity-check: “Would this actually help, or just annoy you?”
Pro tip:
Keep a spreadsheet or doc listing your automations, triggers, and what each does. That way, when something breaks (and it will), you’re not hunting blind.
Step 5: Train Your Reps (Without the Eye Rolls)
No automation works if your team ignores it. Here’s how to get buy-in:
- Show them why you automated: “We saw 30% of demos didn’t get a follow-up—this catches that.”
- Make sure tasks are clear, not vague. “Send pricing email today” beats “Follow up.”
- Let reps snooze or complete tasks easily—don’t make it a punishment.
- Ask for feedback often. If something’s just clutter, kill it.
What to watch for:
If you notice reps bulk-completing tasks without doing the work, your automations are probably too broad or irrelevant.
Step 6: Monitor, Adjust, and Don’t Be Precious
No automation is perfect out of the gate. You’ll need to tweak:
- Check weekly: Are important follow-ups still being missed? Are there too many tasks?
- Look at completion rates: If reps are ignoring or bulk-completing, simplify or cut back.
- Get real-world feedback: Ask, “What’s actually helping you close deals?”
Ignore:
Vanity metrics like “tasks created” or “emails sent.” Focus on actual sales movement and fewer dropped balls.
Step 7: Avoid These Common Mistakes
- Automating everything: More tasks don’t mean more productivity.
- Vague tasks: If a rep can’t tell what to do in 5 seconds, they’ll skip it.
- Never revisiting automations: Sales processes change. Your automations should, too.
- Letting automation hide real problems: If follow-ups aren’t getting done, figure out if it’s a workflow issue, not just a reminder problem.
What About Integrations and Limitations?
Setsail plays nice with most major CRMs and email tools. But integrations can get weird:
- Test before you trust: Sometimes, integrations drop data or miss activities. Double-check that what Setsail “sees” matches reality.
- Data privacy: If you’re in a regulated industry, check what’s being synced.
- Don’t try to replace human judgment: No automation knows your customer as well as you do. Use it to remind, not to replace.
Keep It Simple, Iterate, and Don’t Overthink It
If you take one thing away: automation should make life easier, not busier. Start with your biggest follow-up gaps, automate just those, and see what actually helps. If an automation turns into more hassle than it’s worth, scrap it. Iterate, keep it simple, and—most importantly—make sure your team has more time for selling, not just clicking.