If you’re tired of deals stalling out because someone forgot to send a follow-up, you’re not alone. Sales teams spend way too much time chasing reminders and updating spreadsheets. There’s a better way: automating your follow-up tasks. This guide will show you—step by step—how to do it in Sailes, so you can spend less time on busywork and more time actually selling.
Who’s this for? If you’re running a sales team, managing leads yourself, or just sick of “slipping through the cracks,” this one’s for you. You don’t need to be a tech wizard, but you do need to care about not dropping the ball.
Why Automate Follow-Ups? (And What to Ignore)
Let’s get real: Not every sales task should be automated. But follow-ups—the “Hey, did you get my last email?” messages and reminders to call that lead again—are perfect candidates. Here’s why:
- You’ll actually remember to follow up. No more post-it notes or “circle back” emails stuck in drafts.
- You’ll save time. Less clicking around, more conversations that matter.
- You’ll look sharp. Prospects get timely responses, and you stop looking like you’re making it up as you go.
What to ignore: Overcomplicated automations that try to do too much. If you find yourself diagramming your process on a whiteboard and needing three espresso shots to understand it, you’ve gone too far. Start simple.
Step 1: Map Out Your Follow-Up Points
Before you dive into Sailes, take five minutes to sketch out your sales process. Where do you usually follow up? Typical spots:
- After an initial discovery call
- When you’ve sent a proposal
- If the lead goes quiet for a week
- When a deal is marked “stuck” or “on hold”
Write down the natural moments when a nudge helps. Don’t automate every single interaction—just the ones most likely to slip through the cracks.
Pro tip: If your team keeps missing the same step (say, a reminder to send a contract), start there.
Step 2: Set Up Your Sailes Account (If You Haven’t Already)
If you’re new to Sailes, sign up and get your team invited. The setup is pretty straightforward, but a few pointers:
- Use your work email, so notifications land where you’ll see them.
- Add your teammates early. Automation only helps if everyone’s on the same platform.
- Connect your calendar and email (if Sailes supports direct integration; check documentation). This saves manual switching later.
Skip: Customizing every field right away. Sailes is flexible, but don’t get bogged down. You can tweak as you go.
Step 3: Create Your First Automated Follow-Up Task
Now for the good stuff. Sailes has a “Tasks” or “Automations” feature (names may vary—check the left sidebar or top navigation).
- Go to Tasks/Automations.
- Look for a button like “New Automation” or “Create Task Sequence.”
- Choose a Trigger.
- Example: “When a deal moves to ‘Proposal Sent’ stage.”
- Other options: time-based (e.g., 3 days after last contact), manual trigger, or on a specific event.
- Define the Action.
- Most common: “Create a follow-up task for the assigned rep.”
- You could also set an email reminder, schedule a call, or assign a checklist.
- Set the Timing.
- Example: “2 days after trigger event.”
- Don’t make these immediate—give prospects breathing room.
- Add Details.
- Name the task clearly (“Follow up on proposal: {{Deal Name}}”), set due date, assign to the right rep.
- Use placeholders (like {{First Name}}) to personalize.
Pro tip: Test with yourself first. Trigger the automation, see what task lands in your inbox, and tweak the wording or timing.
Step 4: Build a Simple Sequence (But Don’t Overdo It)
Automations can do more than a single reminder. Most deals need more than one nudge, so consider a basic sequence:
- Day 0: Proposal sent → create a follow-up task for 2 days later.
- Day 2: If no response, generate another task or auto-send a gentle email.
- Day 7: Still nothing? Create a “final check-in” task or mark as “needs review.”
How simple is too simple? If your sequence has more than 3-4 steps, stop and see how it works before adding more. Complex doesn’t mean better.
What to ignore: Automated “breakup emails” that sound robotic or pushy. If your automation makes you cringe, so will your leads.
Step 5: Assign Ownership and Make It Visible
Automation is useless if no one knows what’s happening. Make sure:
- Every task has a clear owner. Use Sailes’ assignment features.
- The follow-up tasks show up on the dashboard, not buried in a hard-to-find tab.
- Reminders and notifications are turned on (but not so many you tune them out).
Pro tip: Have a weekly review. Quickly scan overdue or upcoming tasks to spot bottlenecks.
Step 6: Review, Refine, and Don’t Chase Every Trend
Give your new system a week or two. What’s working? What’s not? Ask your team:
- Are follow-ups actually happening on time?
- Are tasks clear, or do reps ignore them?
- Are any automations annoying or redundant?
Tweak the timing, wording, or triggers as needed. Don’t fall for the “set it and forget it” myth—automation works best when you check in regularly.
Ignore: Fancy AI suggestions or “smart” automations that promise to do everything for you. Most of the time, they’re not as smart as advertised. Trust your process, not the hype.
Step 7: Keep It Human
Automated follow-ups are great for reminders, but don’t let them replace real conversations. Use the task to prompt a call or a personal note, not just another canned email.
- If a lead replies, pause the automation. Nothing says “I’m not paying attention” like a robot email after someone just called you back.
- Personalize whenever possible. Even a small tweak (“Hey Sarah, just checking in about the proposal…”) goes a long way.
Pro tip: Use automation to support your workflow, not dictate it. The best salespeople don’t sound like bots.
Troubleshooting: Common Pitfalls and How to Avoid Them
Problem: Too many tasks, not enough action. - Fix: Review triggers and cut anything that isn’t essential.
Problem: Tasks assigned to the wrong person. - Fix: Double-check your assignment rules in Sailes. Make sure ownership lines up with your real sales process.
Problem: Automation stops working after a Sailes update. - Fix: Check for new permissions or re-authenticate integrations. SaaS tools change—don’t assume it’s “set and forget.”
Problem: Leads complain about too many emails. - Fix: Space out follow-ups more. Never automate daily pings.
Real Talk: What Works (and What Doesn’t)
- Works: Simple reminders, clear ownership, and a short sequence.
- Doesn’t: Do-it-all AI bots, over-customized workflows, or “set and forget” thinking.
- Ignore: Anyone telling you that more automation is always better. Start with what helps your team, not what looks flashy in a demo.
Wrapping Up: Keep It Simple, Iterate Often
Automated follow-up tasks in Sailes can seriously boost your sales productivity—if you keep it simple and check in often. Don’t try to automate your entire process overnight. Start with the steps that matter most, get your team using them, and tweak as you go. The goal isn’t to replace your judgment—it’s to help you spend more time selling, and less time chasing reminders.
If you remember one thing: the best automation is the stuff you barely notice, because it just works. Start small, and build from there.